[ CAS No. 137756-89-9 ] {[proInfo.proName]}

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2D 3D

Structure of 137756-89-9 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 137756-89-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 137756-89-9 ]

SDS Specification

Alternatived Products of [ 137756-89-9 ]

Product Details of [ 137756-89-9 ]

CAS No. :	137756-89-9	MDL No. :	MFCD03095135
Formula :	C₈H₁₁BO₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	KQXBZMDDTQEGMT-UHFFFAOYSA-N
M.W :	165.98	Pubchem ID :	10176286
Synonyms :

Calculated chemistry of [ 137756-89-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	3.0
Molar Refractivity :	47.2
TPSA :	60.69 ?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) :	-7.03 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.4
Log Po/w (WLOGP) :	-1.1
Log Po/w (MLOGP) :	0.06
Log Po/w (SILICOS-IT) :	-0.58
Consensus Log Po/w :	-0.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.29
Solubility :	8.45 mg/ml ; 0.0509 mol/l
Class :	Very soluble
Log S (Ali) :	-1.24
Solubility :	9.53 mg/ml ; 0.0574 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.51
Solubility :	5.07 mg/ml ; 0.0305 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.51

Safety of [ 137756-89-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 137756-89-9 ]

* 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 [ 137756-89-9 ]
Downstream synthetic route of [ 137756-89-9 ]

[ 137756-89-9 ] Synthesis Path-Upstream 1~3

1
[ 4654-39-1 ]
[ 137756-89-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5 h; Stage #2: With hydrogenchloride; Triisopropyl borate In tetrahydrofuran; hexane; water at -78 - 20℃; for 1 h;	To a stirred solution of 4-bromophenethylalcohol (5.00 g, 24.9 mmol) in THF (80 ml) was added a solution of 1.5M n-BuLi in hexane (39.8 ml, 59.7 mmol) at -78° C. over 30 min. After 1 hour, a solution of B(OiPr)3 (8.61 ml, 37.3 mmol) in THF (20 ml) was added slowly to the mixture at -78° C. The resultant mixture was warmed to room temperature, and treated with 2M HCl (100 ml) for 1 hour. This was extracted with CH2Cl2 and dried over MgSO4, then filtered. After evaporation in vacuo, the residue was purified by silica-gel column chromatography eluting with CH2Cl2/MeOH=20/1 to afford 2.61 g (63percent) of the title compound. [2789] 1H-NMR (CD3OD) δ: 7.64-7.48 (2H, m), 7.19-7.13 (2H, m), 3.70 (2H, t, J=7.2 Hz), 2.77 (2H, t, J=7.2 Hz) MS (ESI) m/z: 165 ([M-H]-)
63%	With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 1.5 h;	To a stirred solution of 4-bromophenethylalcohol (5.00 g, 24.9 mmol) in tetrahydrofuran (80 mL) was added a solution of 1.5 M n-butyl lithium in hexane (39.8 mL, 59.7 mmol) at -78° C. over 30 min. After 1 h, a solution of triisopropyl borate (8.61 mL, 37.3 mmol) in tetrahydrofuran (20 mL) was added slowly to the mixture at -78° C. The resultant mixture was warmed to room temperature, and treated with 2 M HCl (100 mL) for 1 h. This mixture was extracted with dichloromethane and dried (MgSO4). After evaporation in vacuo, the residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (20:1) to afford 2.61 g (63percent) of the title compound as white solids

Reference： [1] Patent: US2003/236260, 2003, A1, . Location in patent: Page 114
[2] Patent: US2004/19045, 2004, A1, . Location in patent: Page 52

2
[ 5419-55-6 ]
[ 4654-39-1 ]
[ 7732-18-5 ]
[ 137756-89-9 ]

Yield	Reaction Conditions	Operation in experiment
37%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - 35℃; for 1.5 h; Stage #2: at -78 - 35℃; Stage #3: With ammonium chloride In tetrahydrofuran; hexane	(Step 1) To a solution of 2-(4-bromophenyl)ethanol (3.00 g, 14.9 mmol) in THF (60 mL) was added 1.6 M butyllithium/hexane solution (23.3 mL, 37.3 mmol) at -78° C. and the mixture was stirred at -78° C. for 1 hr and then at room temperature for 30 min. The reaction mixture was cooled again to -78° C. and triisopropylboric acid (7.02 g, 37.3 mmol) was added. The mixture was gradually heated to room temperature. Saturated aqueous ammonium chloride solution (150 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous-sodium sulfate. The solvent was evaporated under reduced pressure, and the concentrated residue was purified by silica gel column chromatography (67-100percent ethyl acetate/hexane-9percent methanol/ethyl acetate) to give [4-(2-hydroxyethyl)phenyl]boronic acid as a colorless amorphous form (925 mg, 37percent).

Reference： [1] Patent: US2015/329556, 2015, A1, . Location in patent: Paragraph 1862-1863

3
[ 4654-39-1 ]
[ 137756-89-9 ]

Yield	Reaction Conditions	Operation in experiment
63%	With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane	Step. 4-(2-hydroxyethyl)phenylboronic acid To a stirred solution of 4-bromophenethylalcohol (5.00 g, 24.9 mmol) in THF (80 ml) was added a solution of 1.5M n-BuLi in hexane (39.8 ml, 59.7 mmol) at -78° C. over 30 min. After 1 hour, a solution of B(OⁱPr)₃ (8.61 ml, 37.3 mmol) in THF (20 ml) was added slowly to the mixture at -78° C. The resultant mixture was warmed to room temperature, and treated with 2M HCl (100 ml) for 1 hour. This was extracted with CH₂Cl₂ and dried over MgSO₄, then filtered. After evaporation in vacuo, the residue was purified by silica-gel column chromatography eluding with CH₂Cl₂/MeOH=20/1 to afford 2.61 g (63percent) of the title compound. ¹H-NMR (CD₃OD) δ: 7.64-7.48 (2H, m), 7.19-7.13 (2H, m), 3.70 (2H, t, J=7.2 Hz), 2.77 (2H, t, J=7.2 Hz) MS (ESI) m/z: 165 ([M-H]^-)

Reference： [1] Patent: US2002/77329, 2002, A1,

[ 137756-89-9 ] Synthesis Path-Downstream 1~2

1
[ 137756-89-9 ]
[ 1221819-46-0 ]
2-(4-(3-((phenylsulfonyl)methyl)oxetan-3-yl)phenyl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide; In 1,4-dioxane; water; at 100℃; for 0.5h;Microwave irradiation;	2-(4-(3-((Phenylsulfonyl)methyl)oxetan-3-yl)phenyl)ethanol To a vial was added the chloro(1,5-cyclooctadiene)rhodium(I), dimer (0.012 g, 0.025 mmol) and 1,4-dioxane (10 mL). The 1.5 M aqueous KOH (0.496 mL, 0.745 mmol) was then added and the reaction stirred for 1 minute at rt. Then the (4-(2-hydroxyethyl)phenyl)boronic acid (0.103 g, 0.621 mmol) and <strong>[1221819-46-0]3-((phenylsulfonyl)methylene)oxetane</strong> (<strong>[1221819-46-0]KSC-352-099</strong>) (0.052 g, 0.248 mmol) in 1 mL dioxane was added and the reaction stirred for 30 minutes at 100 C. in muwaves. The reaction was then cooled to rt and diluted with EtOAc and washed with 1.0 M HCl. The water layer was extracted with EtOAc (3*15 mL). The EtOAc layer was collected and the water was extracted with EtOAc again. The EtOAc layers were combined and dried with MgSO4, filtered and concentrated then purified by reverse-phase MPLC (30 min, 10-100% MeCN:water) to produce pure 2-(4-(3-((phenylsulfonyl)methyl) oxetan-3-yl)phenyl)ethanol (0.063 g, 0.190 mmol, 76% yield). 1H NMR (400 MHz, CDCl3): delta 7.55-7.52 (m, 2H), 7.50-7.46 (m, 1H), 7.36-7.31 (m, 2H), 7.09 (d, J=8.4 Hz, 2H), 7.01 (d, J=8.3 Hz, 2H), 5.03 (d, J=6.4 Hz, 2H), 4.93 (d, J=6.4 Hz, 2H), 4.03 (s, 2H), 3.82 (t, J=7.3 Hz, 2H), 2.80 (t, J=7.3 Hz, 2H).

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 8540 - 8562
[2]Patent: US2015/238473,2015,A1 .Location in patent: Paragraph 0272

2
[ 137756-89-9 ]
[ 876343-10-1 ]
2-(4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
762 mg	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In propan-1-ol; water; at 105℃;Inert atmosphere;	A 100 ml round bottom flask containing a mixture of <strong>[876343-10-1]4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine</strong> (1 .2 g, 4.29 mmol), 4-(2-hydroxyethyl)phenylboronic acid (750 mg, 4.29 mmol), an aq. solution of Na2C03(2.0 M) (4.72 ml, 9.45 mmol), PdCl2(PPh3)2 (154 mg, 0.215 mmol) and 1 -propanol (36 ml) was purged with N2at RT and then stirred at 105C overnight. The mixture was concentrated to dryness and purified by chromatography on silica gel eluting with EtOAc in CHX (from 40 to 100%) to give the title compound as a solid (762 mg).Method A: Rt = 0.82 min; [M+H]+= 274.0.
762 mg	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In propan-1-ol; water; at 105℃;Inert atmosphere;	A yellow milky mixture of <strong>[876343-10-1]4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine</strong> (1.2 g, 4.29 mmol), 4-(2- hydroxyethyl)phenylboronic acid (750 mg, 4.29 mmol), Na2C03 2M in water (4.72 ml, 9.45 mmol) and PdCl2(PPh3)2 (154 mg, 0.215 mmol) in 1 -propanol (36 ml) was flushed with N2 at RT and then stirred in a preheated oil bath at 105C. After stirring at 105C overnight, the brown mixture was concentrated until dryness and dried under HV pump to yield a dark solid. Purification of the crude by flash chromatography on silica gel eluting with 40 - 100% EtOAc in CHX afforded 762 mg of the title compound as a yellow solid. LC-MS (Method A): Rt = 0.82 min, [M+H]+ = 274.0.

Reference： [1]Patent: WO2019/186343,2019,A1 .Location in patent: Page/Page column 82
[2]Patent: WO2019/186358,2019,A1 .Location in patent: Page/Page column 82-83

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Isomers

Technical Information

? Appel Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chugaev Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Friedel-Crafts Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Martin's Sulfurane Dehydrating Reagent ? Mitsunobu Reaction ? Moffatt Oxidation ? Oxidation of Alcohols by DMSO ? Preparation of Alcohols ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alcohols ? Reactions of Benzene and Substituted Benzenes ? Reactions with Organometallic Reagents ? Ritter Reaction ? Sharpless Olefin Synthesis ? Swern Oxidation ? Vilsmeier-Haack Reaction

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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. 137756-89-9 ] {[proInfo.proName]}

Quality Control of [ 137756-89-9 ]

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Calculated chemistry of [ 137756-89-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 137756-89-9 ]

Application In Synthesis of [ 137756-89-9 ]

[ 137756-89-9 ] Synthesis Path-Upstream 1~3

[ 137756-89-9 ] Synthesis Path-Downstream 1~2

Technical Information

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Organoboron

Aryls

Alcohols

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Prevention

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Disposal

Physical hazards

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Environmental hazards

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[ 137756-89-9 ]