[ CAS No. 1066-54-2 ] {[proInfo.proName]}

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Quality Control of [ 1066-54-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1066-54-2 ]

SDS Specification

Alternatived Products of [ 1066-54-2 ]

Product Citations

Investigating the Effects of Donors and Alkyne Spacer on the Properties of Donor-Acceptor-Donor Xanthene-Based Dyes

Rajapaksha, Ishanka N. ; Wang, Jing ; Leszczynski, Jerzy , et al. Molecules,2023,28(13):4929. DOI: 10.3390/molecules28134929 PubMed ID: 37446594

Abstract: NIR dyes have become popular for many applications, including biosensing and imaging. For this reason, the mol. switch mechanism of the xanthene dyes makes them useful for in vivo detection and imaging of bioanalytes. Our group has been designing NIR xanthene-based dyes by the donor-acceptor-donor approach; however, the equilibrium between their opened and closed forms varies depending on the donors and spacer. We synthesized donor-acceptor-donor NIR xanthene-based dyes with an alkyne spacer via the Sonogashira coupling reaction to investigate the effects of the alkyne spacer and the donors on the maximum absorption wavelength and the mol. switching (ring opening) process of the dyes. We evaluated the strength and nature of the donors and the presence and absence of the alkyne spacer on the properties of the dyes. It was shown that the alkyne spacer extended the conjugation of the dyes, leading to absorption wavelengths of longer values compared with the dyes without the alkyne group. In addition, strong charge transfer donors shifted the absorption wavelength towards the NIR region, while donors with strong π-donation resulted in xanthene dyes with a smaller equilibrium constant DFT/TDDFT calculations corroborated the exptl. data in most of the cases. Dye 2 containing the N,N-dimethylaniline group gave contrary results and is being further investigated.

Keywords: donor-acceptor-donor ; NIR dyes ; xanthene dyes ; amine donors ; alkyne spacers

Purchased from AmBeed: 589-87-7 ; 768-60-5 ; 201802-67-7 ; 57102-42-8 ; 17573-94-3 ; 1066-54-2 ; 205877-26-5 ; 28611-39-4 ; 262861-81-4 ; 1195931-66-8

Product Details of [ 1066-54-2 ]

CAS No. :	1066-54-2	MDL No. :	MFCD00008569
Formula :	C₅H₁₀Si	Boiling Point :	No data available
Linear Structure Formula :	HCC(Si(CH₃)₃)	InChI Key :	CWMFRHBXRUITQE-UHFFFAOYSA-N
M.W :	98.22	Pubchem ID :	66111
Synonyms :

Calculated chemistry of [ 1066-54-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.6
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	32.18
TPSA :	0.0 ?2

Pharmacokinetics

GI absorption :	Low
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) :	-5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.25
Log Po/w (XLOGP3) :	2.34
Log Po/w (WLOGP) :	1.58
Log Po/w (MLOGP) :	2.08
Log Po/w (SILICOS-IT) :	-0.18
Consensus Log Po/w :	1.61

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.92
Solubility :	1.17 mg/ml ; 0.0119 mol/l
Class :	Very soluble
Log S (Ali) :	-1.98
Solubility :	1.03 mg/ml ; 0.0105 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.15
Solubility :	7.02 mg/ml ; 0.0714 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.95

Safety of [ 1066-54-2 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P261-P305+P351+P338	UN#:	1993
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 1066-54-2 ]

* 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 [ 1066-54-2 ]
Downstream synthetic route of [ 1066-54-2 ]

[ 1066-54-2 ] Synthesis Path-Upstream 1~1

1
[ 223463-13-6 ]
[ 1066-54-2 ]
[ 111770-86-6 ]

Reference： [1] Catalysis Communications, 2014, vol. 47, p. 40 - 44

[ 1066-54-2 ] Synthesis Path-Downstream 1~10

1
[ 34259-99-9 ]
[ 1066-54-2 ]
[ 111600-89-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 823 - 828

2
[ 67442-07-3 ]
[ 1066-54-2 ]
[ 18245-82-4 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5031 - 5034

3
[ 5780-66-5 ]
[ 1066-54-2 ]
1-pyrazin-2-yl-3-trimethylsilanyl-prop-2-yn-1-ol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 12050 - 12051

4
[ 157942-12-6 ]
[ 1066-54-2 ]
[ 478169-68-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 50℃; for 4h;	Methyl 3-hydroxy-4-iodobenzoate (5.22 g, 18.8 mmol) is combined with trimethylsilylacetylene (3.71 mL, 26.3 mmol), bis(triphenylphosphine)palladium dichloride (386 mg, 0.55 mmol) and cuprous iodide (54 mg, 0.28 mmol) in THF (20 mL)/CHCl3 (40 mL) in a dry flask, under nitrogen. Triethylamine (8.14 mL, 58.4 mmol) is added and the mixture is heated to 50° C. for 4 h. The mixture is diluted with CHCl3 (60 mL), washed with 5percent HCl (2.x.40 mL), dried (MgSO4) and concentrated to a brown oily-solid (8.31 g). The crude material is chromatographed over a standard 90 g Biotage column, eluting with 10percent EtOAc/hexane (1 L) followed by 15percent EtOAc/hexane (1 L). The appropriate fractions are combined and concentrated to afford 4.22 g (91percent) of methyl 3-hydroxy-4-[(trimethylsilyl)ethynyl]benzoate as a yellow solid. HRMS (FAB) calcd for C13H16O3SI+H: 249.0947, found 249.0947 (M+H)+.
4.22 g (91%)	With triethanolamine; copper(I) iodide;bis(triphenylphosphine)palladium(II) dichloride; In tetrahydrofuran; hexane; chloroform; ethyl acetate;	Methyl 3-hydroxy-4-iodobenzoate (5.22 g, 18.8 mmol) is combined with trimethylsilylacetylene (3.71 mL, 26.3 mmol), bis(triphenylphosphine)palladium dichloride (386 mg, 0.55 mmol) and cuprous iodide (54 mg, 0.28 mmol) in THF (20 mL) CHCl3 (40 mL) in a dry flask, under nitrogen. TEA (8.14 mL<58.4 mmol) is added and the mixture is heated to 50° C. for 4 h. The mixture is diluted with CHCl3 (60 mL), washed with 5percent HCl (2*40 mL), dried over anhydrous MgSO4 and concentrated to a brown paste (8.31 g). The crude material is chromatographed over a standard 90 g Biotage column, eluding with 10percent EtOAc/hexane (1 L) followed by 15percent EtOAc/hexane (1 L). The appropriate fractions are combined and concentrated to afford 4.22 g (91percent) of methyl 3-hydroxy-4-[(trimethylsilyl)ethynyl]benzoate as a yellow solid. HRMS (FAB) calcd for C13H16O3SI+H1: 249.0947, found 249.0947.
4.22 g (91%)	With triethanolamine; copper(I) iodide;bis(triphenylphosphine)palladium(II) dichloride; In tetrahydrofuran; hexane; chloroform; ethyl acetate;	Methyl-3-hydroxy-4-iodobenzoate (5.22 g, 18.8 mmol) is combined with trimethylsilylacetylene (3.71 mL, 26.3 mmol), bis(triphenylphosphine)palladium dichloride (386 mg, 0.55 mmol) and cuprous iodide (54 mg, 0.28 mmol) in THF (20 mL)/CHCl3 (40 mL) in a dry flask under nitrogen. TEA (8.14 mL<58.4 mmol) is added and the mixture is heated to 50° C. for 4 h. The mixture is diluted with CHCl3 (60 mL), washed with 5percent HCl (2*40 mL), dried over MgSO4 and concentrated to a brown oily-solid (8.31 g). The crude material is chromatographed over a standard 90 g Biotage column, eluding with 10percent EtOAc/hexane (1 L) followed by 15percent EtOAc/hexane (1 L). The appropriate fractions are combined and concentrated to afford 4.22 g (91percent) of methyl 3-hydroxy-4-[(trimethylsilyl)ethynyl]benzoate as a yellow solid. HRMS (FAB) calcd for C13H16O3Si+H: 249.0947, found 249.0947 (M+H)+.

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4425 - 4436
[2]Patent: US2003/232853,2003,A1 .Location in patent: Page 38
[3]Patent: US2003/73707,2003,A1
[4]Patent: US2003/105089,2003,A1

5
[ 34259-99-9 ]
[ 1066-54-2 ]
[ 630094-87-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; at 75℃; for 5h;Inert atmosphere;	[544] Example 129 - 3-ri-Methyl-5-(4-methyl-cvclohexyl)-l,2,3,6-tetrahydro-pyridin-4-yl1-5-(4-HCl; [545] Bromothiazole (1 g, 6.10 mmol), copper (1) iodide (50 mg, 0.26 mmol), Pd(PPh3)2Cl2 (66 mg, 0.94 mmol), and trimethylsilylacetylene (1.04 mL, 7.36 mmol) in TEA (4 mL) were degassed, placed under N2, and stirred at 75 °C for 5 hr. The reaction mixture was cooled to RT and partitioned between DCM and water. The organic phase was dried over MgS04, concentrated, and column chromatography using 0-25percent EtOAc/hexane afforded 129A as a brown residue (1.05 g, 95 percent). MS calcd: (M+H)+ = 182. MS found: (M+H)+ = 182.
79%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 80℃; for 3h;Inert atmosphere;	The mixture of 5a (5 g, 30.5 mmol), Trimethylsilylacetylene (3.6 g, 36.6 mmol), Pd(PPh3)2C12 (210 mg, 0.3 mmol) and Cul (85 mg, 0.45 mmol) in TEA (150 mE) was heated at 80° C. for 3 h under N2, then cooled, diluted with Et20 (100 mE) and washed with brine (100 mE). The organic phase was separated, dried over anhydrous Na2504 and concentrated under reduced pressure. The residue was purified by colunm chromatography (silica, EtOAc/petroleum ether 1:15) to provide Sb (4.3 g, 79percent yield) as a yellow oil. ?H-NMR (CDC13, 400 MHz): oe=8.74 (d, 1H), 7.53 (d, 1H), 0.26 (s, 9H)
72%		Compound 11A was prepared following step 4A starting with 0.59 g of <strong>[34259-99-9]<strong>[34259-99-9]4-bromothiazol</strong>e</strong> and substituting 3-phenyl-1-propyne with trimethylsilyl acetylene. Yield: 0.475 g (72percent).

72.4%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 75℃; for 5h;Inert atmosphere;	4- Bromothiazole (1 g, 6.1 mmol), Cul (58.1 mg, 0.3 mmol), Pd(PPh3)2Cl2 (128.4 mg, 0.18 mmol), and ethynyl(trimethyl)silane (898.2 mg, 9.15 mmol) in TEA (4 mL) were degassed, placed under N2, and stirred at 75 °C for 5 hr. The reaction mixture was cooled to RT and partitioned between DCM and water. The organic phase was dried over MgSC , concentrated, and column chromatography using 0-25percent EtOAc/hexane afforded the title product 800 mg (72.4percent) as a brown oil. ESI-MS m/z calcd for [C8Hi2NSSi]+ (M+H)+: 182.0; found: 182.1.
	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 75℃; for 5h;	Intermediate 4; 4-[(Trimethylsilyl)ethynyl]-1 ,3-thiazole; 4-Bromo-1 ,3-thiazole (1 g), copper (I) iodide (50 mg), Pd(PPh3)2CI2 (66 mg), trimethylsilyl acetylene (1.04 ml_), and triethylamine (4 ml.) were degassed and placed under a nitrogen atmosphere in a Reactivial.(TM). , then heated at 75°C for 5 h. The reaction mixture was allowed to cool, then partitioned between DCM and water. The organic phase was dried by using a hydrophobic frit, and the solvent removed under vacuum to give an oil. This was then purified by ISCO companion silica chromatography eluting with a gradient of EtOAc /cyclohexane (0percent to 25percent) to give the title compound MS calcd for (C8H11 NSiS+ H)+: 182MS found (electrospray): (M+H)+ = 182

Reference： [1]Patent: WO2012/83105,2012,A1 .Location in patent: Page/Page column 122-123
[2]Patent: US2015/252021,2015,A1 .Location in patent: Paragraph 0253; 0254
[3]Patent: WO2003/99206,2003,A2 .Location in patent: Page 42
[4]Patent: WO2018/11093,2018,A1 .Location in patent: Page/Page column 75
[5]Patent: WO2008/125599,2008,A1 .Location in patent: Page/Page column 26

6
[ 1006-33-3 ]
[ 1066-54-2 ]
C₁₃H₁₅FOSi [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2423 - 2432

7
[ 78775-11-8 ]
[ 1066-54-2 ]
C₁₃H₁₆OSi [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2318 - 2321

8
[ 13195-50-1 ]
[ 1066-54-2 ]
[ 294638-17-8 ]

Reference： [1]Organometallics,2014,vol. 33,p. 4655 - 4671

9
[ 3883-58-7 ]
[ 1066-54-2 ]
3-hydroxy-2,2-dimethyl-3-[(trimethylsilyl)ethynyl]cyclopentanone [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 1392 - 1397

10
[ 22282-75-3 ]
[ 1066-54-2 ]
3-fluoro-4-((trimethylsilyl)ethynyl)pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 9756 - 9783

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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. 1066-54-2 ] {[proInfo.proName]}

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