[ CAS No. 87199-17-5 ] {[proInfo.proName]}

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Quality Control of [ 87199-17-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Citations Expand+

Additive Mixing of Emissive Ligands in Covalent Organic Frameworks for White Light Emission

Nyakuchena, James ; Chiromo, Humphrey ; Radpour, Shahrzad , et al. ACS Appl. Mater. Interfaces,2024,16(34):44921-44926. DOI: 10.1021/acsami.4c09728 PubMed ID: 39137062

Abstract: Emissive covalent organic frameworks (COFs) are a promising class of crystalline materials that have demonstrated applications for sensing and light-emitting diodes. However, white light emission from a single COF has not been achieved yet as it requires multicomponent organic chromophores that simultaneously emit blue, green, and red light. In this work, we report the successful synthesis of a single COF with efficient white light emission by utilizing tunable emission properties of 2,1,3- benzothiadazole after incorporating different functional groups on its core structure, which results in the formation of three ligands, i.e., 4′,4-(benzothiadiazole-4,7-diyl)-dibenzaldehyde (BTD), 4,4′-(benzoselenadiazole-4,7-diyl)-dibenzaldehyde (BSD), and 4,4′-(naphtho[2,3-c][1,2,3] selenadiazole-4,9-diyl)-dibenzaldehyde (NSD), that emit in the blue, green, and red regions of the visible light spectrum. We show that white light emission can only occur when BTD, BSD, and NSD are assembled in a single COF structure due to the facilitated energy transfer process from BTD to BSD/NSD. This work demonstrates a unique approach to developing new white light-emitting materials based on the COF structure.

Keywords: covalent ; organic ; framework ; emissive ; white ; light

Purchased from AmBeed: 13214-70-5 ; 15155-41-6 ; 87199-17-5 ; 78525-34-5

Photophysical and Cellular Studies of pH-Sensitive Boron-Functionalised Far-Red Fluorophores

Anita Marfavi ; Liam D. Adair ; Elizabeth J. New , et al. J. Organomet. Chem.,2024,123132. DOI: 10.1016/j.jorganchem.2024.123132

Abstract: Two novel chromenylium-based probes were developed by functionalisation of the 5-position of the xanthene core with either a para-N-methyldiaminoacetic acid (MIDA) boronate ester (CRpMD) or closo?1,7-carborane (CRmCB). CRpMD revealed near-infrared emission at 655 nm, demonstrating a bathochromic shift compared to the analogous phenyl derivative (CRPh). Both boron-containing probes were found to be sensitive to changes in acidic pH, with CRpMD also displaying a dual fluorescence response at alkaline pH (pKa1 = 2.40 and pKa2 = 9.16). CRmCB showed a ca. 3-fold increase in fluorescence intensity at 638 nm from pH 7.01 to 2.00, with a pKa = 2.08. Moreover, CRpMD and CRmCB were successfully taken up by A549 lung cancer cells to assess their intracellular biodistributions, thereby showcasing the future potential of these probes for time-resolved pH measurements using confocal microscopy.

Keywords: Near-infrared ; Fluorescence microscopy ; Fluorescent probes ; BoronpH sensor

Purchased from AmBeed: 4408-64-4 ; 5809-23-4 ; 87199-17-5

Product Details of [ 87199-17-5 ]

CAS No. :	87199-17-5	MDL No. :	MFCD00151823
Formula :	C₇H₇BO₃	Boiling Point :	-
Linear Structure Formula :	OCH(C₆H₄)B(OH)₂	InChI Key :	VXWBQOJISHAKKM-UHFFFAOYSA-N
M.W :	149.94	Pubchem ID :	591073
Synonyms :

Calculated chemistry of [ 87199-17-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	41.66
TPSA :	57.53 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.29
Log Po/w (WLOGP) :	-0.82
Log Po/w (MLOGP) :	-0.36
Log Po/w (SILICOS-IT) :	-0.6
Consensus Log Po/w :	-0.3

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.22
Solubility :	8.95 mg/ml ; 0.0597 mol/l
Class :	Very soluble
Log S (Ali) :	-1.06
Solubility :	13.1 mg/ml ; 0.087 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.22
Solubility :	9.08 mg/ml ; 0.0605 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.35

Safety of [ 87199-17-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P272-P273-P280-P302+P352-P333+P313-P362+P364-P501	UN#:	N/A
Hazard Statements:	H317-H401	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 87199-17-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 87199-17-5 ]
Downstream synthetic route of [ 87199-17-5 ]

[ 87199-17-5 ] Synthesis Path-Upstream 1~2

1
[ 392-83-6 ]
[ 87199-17-5 ]
[ 198205-95-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium carbonate In 1,4-dioxane; water at 80 - 100℃;	To a stirred solution of 2-trifluromethyl-bromobenzene (0.7 g, 2.75 mmol) and 4-carbaldehyde boronic acid (0.5 g, 3.3 mmol) in dioxane (20 ml_) under nitrogen at 80 ⁵C was added Pd(PPh₃)₄ (0.05 g) followed by the addition of a solution of Na₂CO₃ (0.7 g) in H₂O (5 m). The mixture was stirred at 100 ⁵C for 6 h. The solvent was evaporated and the residue was diluted to 50 ml with EtOAc and washed with H₂O. The solvent was devaporated to dryness and the residue was purified by FCC (SiO₂) to give the title compound (0.61 g; 88percent), as creamy solid. ¹H-NMR (CDCI₃) 7.49 (d, 1 H, J = 7.41 Hz); 7.48 (d, 2H, J = 8.13 Hz); 7.61 - 7.53 (m, 2H); 7.76 (d, 1 H, J = 7.8 Hz); 7.91 (d, 2H, J = 8.34 Hz); 10.07 (s, 1 H).

Reference： [1] Patent: WO2010/42998, 2010, A1, . Location in patent: Page/Page column 95

2
[ 87199-17-5 ]
[ 283173-50-2 ]

Reference： [1] Patent: WO2018/140377, 2018, A1,

[ 87199-17-5 ] Synthesis Path-Downstream 1~10

1
[ 87199-17-5 ]
3-pyridyl halide [ No CAS ]
[ 4385-76-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 631 - 634

2
[ 87199-17-5 ]
[ 302348-51-2 ]

Reference： [1]Synthetic Communications,2002,vol. 32,p. 2669 - 2676
[2]Molecules,2013,vol. 18,p. 12346 - 12367

3
[ 1120-95-2 ]
[ 87199-17-5 ]
4-[Pyridazin-3-yl]-Benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; for 20h;Heating / reflux;	Step B Ethanol (10 ml) and 1.0M Na2CO3 (18 ml) were added to a suspension of the compound from step A (2.8 g, 24.0 mmole), 4-formylphenylboronic acid (4.7 g, 31.2 mmole), and tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmole0 in toluene (35 ml). The mixture was refluxed for 20 hours then cooled, diluted with EtOAc, washed with NaHCO3, washed with brine, dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 4:1 hexanes/EtOAc) yielded 4.1 g (93percent) of 4-(3-pyridazinyl)benzaldehyde.

Reference： [1]Patent: US2005/250713,2005,A1 .Location in patent: Page/Page column 30

4
[ 475160-93-1 ]
[ 87199-17-5 ]
[ 224311-51-7 ]
[ 475160-94-2 ]

Yield	Reaction Conditions	Operation in experiment
63%	With KF;palladium diacetate; In tetrahydrofuran;	(4'-Formylbiphenyl-2-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S29). 4-Formylphenylboronic acid (4.97 g, 33.2 mmol), aryl bromide S28 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.884 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated moderately (30° C.) with stirring. After 24 h, the reaction was diluted with CH2Cl2 and was washed with 1 M NaOH. The aqueous layer was extracted with CH2Cl2 and the combined organics were then washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude solid was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain a white solid (6.0 g, 63percent). 1H NMR (400 MHz, d6-DMSO): delta10.04 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.88 (d, 2H, J=7.5 Hz), 7.82 (t, 1H, J=5.9 Hz, NH), 7.67 (d, 2H, J=7.5 Hz), 7.59 (d, 2H, J=8.2 Hz), 7.43-7.30 (m, 7H), 7.24 (d, 1H, J=7.7 Hz), 4.29 (d, 2H, J=7.0 Hz), 4.19 (t, 1H, J=7.0 Hz), 4.12 (d, 2H, J=5.9 Hz). APCI/MS: 434 (M+H+).
63%	With KF;palladium diacetate; In tetrahydrofuran;	(4'-Formylbiphenyl-2-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S29). 4-Formylphenylboronic acid (4.97 g, 33.2 mmol), aryl bromide S28 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.884 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated moderately (30° C.) with stirring. After 24 h, the reaction was diluted with CH2Cl2 and was washed with 1 M NaOH. The aqueous layer was extracted with CH2Cl2 and the combined organics were then washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude solid was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain a white solid (6.0 g, 63percent). 1H NMR (400 MHz, d6-DMSO): delta10.04 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.88 (d, 2H, J=7.5 Hz), 7.82 (t, 1H, J=5.9 Hz, NH), 7.67 (d, 2H, J=7.5 Hz), 7.59 (d, 2H, J=8.2 Hz), 7.43-7.30 (m, 7H), 7.24 (d, 1H, J=7.7 Hz), 4.29 (d, 2H, J=7.0 Hz), 4.19 (t, 1H, J=7.0 Hz), 4.12 (d, 2H, J=5.9 Hz). APCI/MS: 434 (M+H+).

Reference： [1]Patent: US2003/187027,2003,A1
[2]Patent: US2004/72849,2004,A1

5
[ 87199-17-5 ]
[ 224311-51-7 ]
[ 475160-92-0 ]
[ 475160-95-3 ]
[ 475160-94-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With KF;palladium diacetate; In tetrahydrofuran;	(4'-Formylbiphenyl-3-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S30). 4-Formylphenylboronic acid (5.0 g, 33 mmol), aryl bromide S27 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.88 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated to reflux with stirring. After 5 h, the reaction was diluted with ethyl acetate, filtered through a celite pad and washed with 1 M NaOH. The aqueous layer was extracted with ethyl acetate and the combined organics were then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford an orange oil (13 g). The crude oil was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain aldehyde S29 as a yellow oil (5.7 g, 60percent). 1H NMR (400 MHz, CDCl3): delta10.06 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.76 (d, 2H, J=7.5 Hz), 7.74 (d, 2H, J=8.2 Hz), 7.59 (d, 2H, J=7.5 Hz), 7.56 (m, 1H), 7.55 (s, 1H), 7.46 (dd, 1H, J=7.9 Hz, 7.9 Hz), 7.39 (dd, 2H, J=7.5 Hz, 7.5 Hz), 7.33 (m, 1H), 7.29 (dd, 2H, J=7.5 Hz, 7.5 Hz), 5.16 (broad s, 1H), 4.48 (d, 2H, J=7.0 Hz), 4.47 (s, 2H), 4.24 (t, 1H, J=7.0 Hz). ESI/MS: 456 (M+Na+).
60%	With KF;palladium diacetate; In tetrahydrofuran;	(4'-Formylbiphenyl-3-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S30). 4-Formylphenylboronic acid (5.0 g, 33 mmol), aryl bromide S27 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.88 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated to reflux with stirring. After 5 h, the reaction was diluted with ethyl acetate, filtered through a celite pad and washed with 1 M NaOH. The aqueous layer was extracted with ethyl acetate and the combined organics were then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford an orange oil (13 g). The crude oil was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain aldehyde S29 as a yellow oil (5.7 g, 60percent). 1H NMR (400 MHz, CDCl3): delta10.06 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.76 (d, 2H, J=7.5 Hz), 7.74 (d, 2H, J=8.2 Hz), 7.59 (d, 2H, J=7.5 Hz), 7.56 (m, 1H), 7.55 (s, 1H), 7.46 (dd, 1H, J=7.9 Hz, 7.9 Hz), 7.39 (dd, 2H, J=7.5 Hz, 7.5 Hz), 7.33 (m, 1H), 7.29 (dd, 2H, J=7.5 Hz, 7.5 Hz), 5.16 (broad s, 1H), 4.48 (d, 2H, J=7.0 Hz), 4.47 (s, 2H), 4.24 (t, 1H, J=7.0 Hz). ESI/MS: 456 (M+Na+).

Reference： [1]Patent: US2003/187027,2003,A1
[2]Patent: US2004/72849,2004,A1

6
[ 33543-78-1 ]
[ 87199-17-5 ]
[ 920511-27-9 ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen;di-mu-hydroxo-bis[(N,N,N?,N?-tetramethylethylene-diamine)copper(II)] chloride; In 1,2-dichloro-ethane; at 60℃; for 20h;	Description 45; Ethyl 1-(4-formylphenyl)-1H-imidazole-2-carboxylate (D45); <strong>[33543-78-1]Ethyl imidazole-2-carboxylate</strong> (140 mg, 1.0 mmol), 4-formylbenzeneboronic acid (300 mg, 2.0 mmol) and catalyst [Copper(OH).TMEDA]2Cl2 (46 mg, 0.10 mmol) were dissolved in 1,2-dichloroethane (5 ml) and heated to 60° C. under an O2 atmosphere for 20 h. The mixture was diluted with DCM, filtered through Celite and evaporated to dryness. The crude residue was purified by column chromatography on silica, eluting with a 0-5percent [2M NH3 in MeOH]/DCM gradient to give the title compound (152 mg). deltaH (CDCl3, 250 MHz) 1.32 (3H, t), 4.32 (2H, q), 7.22 (1H, s), 7.34 (1H, s), 7.52 (2H, d), 8.01 (2H, d), 10.11 (1H, s). MS (ES): MH+ 245.
	With oxygen;di-mu-hydroxo-bis[(N,N,N?,N?-tetramethylethylene-diamine)copper(II)] chloride; In 1,2-dichloro-ethane; at 60℃; for 20h;	Description 45; Ethyl 1-(4-formylphenyl)-1H-imidazole-2-carboxylate (D45); <strong>[33543-78-1]Ethyl imidazole-2-carboxylate</strong> (140mg, 1. Ommol), 4-formylbenzeneboronic acid (300mg, 2.0mmo.) and catalyst [Copper(OH).TMEDA] 2CI2 (46mg, 0.1 Ommol) were dissolved in 1 ,2-dichloroethane (5ml) and heated to 60°C under an O2 atmosphere for 2Oh. The mixture was diluted with DCM, filtered through Celite and evaporated to dryness. The crude residue was purified by column chromatography on silica, eluting with a 0-5percent [2M NH3 in MeOH]/DCM gradient to give the title compound (152mg). deltaH (CDCI3, 250MHz) 1.32 (3H, t), 4.32 (2H, q), 7.22 (1 H, s), 7.34 (1H, s), 7.52 (2H, d), 8.01 (2H, d), 10.11 (1H, s). MS (ES): MH+ 245.

Reference： [1]Patent: US2008/312209,2008,A1 .Location in patent: Page/Page column 19
[2]Patent: WO2007/7018,2007,A1 .Location in patent: Page/Page column 54

7
[ 87199-17-5 ]
[ 34259-99-9 ]
[ 127406-12-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 16h;Reflux; Inert atmosphere;	To a solution of <strong>[34259-99-9]<strong>[34259-99-9]4-bromothiazol</strong>e</strong> (see The Journal of Organic Chemistry, 71, 3754 (2006)) (1.31 g, 7.98 mmol) in 1,2-dimethoxyethane (38.0 ml) were added 4-formylphenylboronic acid (1.45 g, 9.67 mmol), sodium hydrogencarbonate (2.00 g, 23.8 mmol) and water (19 ml), which was deaerated under reduced pressure, followed by argon substitution. Tetrakis(triphenylphosphine)palladium (270 mg, 0.234 mmol) was then added, followed by heating to reflux for 16 hours under argon atmosphere. After completion of the reaction, a saturated aqueous sodium chloride solution was added to the reaction solution, followed by extraction with chloroform. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=4:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.29 g) as a slightly yellow solid. (Yield: 85percent) Mass spectrum (CI, m/z): 190 (M++1). 1H-NMR spectrum (CDCl3, ppm): 10.05 (s, 1H), 8.93 (d, J=2.0Hz, 1H), 8.14-8.10 (m, 2H), 799-7.94 (m, 2H), 7.73 (d, J=2.0Hz, 1H).
85%	With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 16h;Inert atmosphere; Reflux;	15-(a) 4-(Thiazol-4-yl)benzaldehyde To a solution of <strong>[34259-99-9]<strong>[34259-99-9]4-bromothiazol</strong>e</strong> (see The Journal of Organic Chemistry, 71, 3754 (2006)) (1.31 g, 7.98 mmol) in 1,2-dimethoxyethane (38.0 ml) were added 4-formylphenylboronic acid (1.45 g, 9.67 mmol), sodium hydrogencarbonate (2.00 g, 23.8 mmol) and water (19 ml), which was deaerated under reduced pressure, followed by argon substitution. Tetrakis(triphenylphosphine)palladium (270 mg, 0.234 mmol) was then added, followed by heating to reflux for 16 hours under argon atmosphere. After completion of the reaction, a saturated aqueous sodium chloride solution was added to the reaction solution, followed by extraction with chloroform. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=4:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.29 g) as a slightly yellow solid. (Yield: 85percent) Mass spectrum (CI, m/z): 190 (M++1). 1H-NMR spectrum (CDCl3, deltappm): 10.05 (s, 1H), 8.93 (d, J=2.0Hz, 1H), 8.14-8.10 (m, 2H), 7.99-7.94 (m, 2H), 7.73 (d, J=2.0Hz, 1H).

Reference： [1]Patent: EP2264009,2010,A1 .Location in patent: Page/Page column 106
[2]Patent: EP2415763,2012,A1 .Location in patent: Page/Page column 108

8
[ 87199-17-5 ]
[ 57103-20-5 ]
C₃₂H₂₁NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.24%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; toluene; at 90℃;Inert atmosphere;	B.Compound <strong>[57103-20-5]3,6-dibromo-9-phenylcarbazole</strong> (157.7 mg, 0.40 mmol)4-formylphenylboronic acid (129.7 mg, 0.87 mmol),Bis (triphenylphosphine) palladium dichloride Pd (PPh3) 2Cl2 (28.1 mg, 0.04 mmol)Was dissolved in 40 mL of a mixed solution of toluene and tetrahydrofuran (Vtoluene: VTHF = 1: 1)The reaction was refluxed at 90 ° C under nitrogen,Thin layer chromatography to the reaction is complete.After the resulting solution was spin off the organic solvent,Extracted with ethyl acetate,Organic layer washed three times,Saturated NaCl solution once,Dried over anhydrous sodium sulfate,The solvent is evaporated under reduced pressure;The crude product was passed through a column of petroleum ether and ethyl acetate mixed solvent (20: 1)4,4 '- (9-phenyl-9H-carbazole-3,6-diyl) benzaldehyde(Yellow powder, 123.1 mg, yield 68.24percent).

Reference： [1]Patent: CN106883182,2017,A .Location in patent: Page/Page column 11; 12

9
[ 4181-20-8 ]
[ 87199-17-5 ]
4',4''',4'''''-nitrilotris(([1,1'-biphenyl]-4-carbaldehyde)) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 14149 - 14153
Angew. Chem.,2017,vol. 129,p. 14337 - 14341,5

10
[ 10016-52-1 ]
[ 87199-17-5 ]
C₂₆H₁₆O₃ [ No CAS ]

Reference： [1]Journal of Materials Chemistry A,2018,vol. 6,p. 19775 - 19781

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Technical Information

? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Stetter Reaction ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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[ 87199-16-4 ]

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 87199-17-5 ] {[proInfo.proName]}

Quality Control of [ 87199-17-5 ]

Related Doc. of [ 87199-17-5 ]

Product Citations Expand+

Product Details of [ 87199-17-5 ]

Calculated chemistry of [ 87199-17-5 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 87199-17-5 ]

Application In Synthesis of [ 87199-17-5 ]

[ 87199-17-5 ] Synthesis Path-Upstream 1~2

[ 87199-17-5 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 87199-17-5 ]

Organoboron

Aryls

Aldehydes

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 87199-17-5 ]