[ CAS No. 4654-39-1 ] {[proInfo.proName]}

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2D 3D

Structure of 4654-39-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 4654-39-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4654-39-1 ]

SDS Specification

Alternatived Products of [ 4654-39-1 ]

Product Details of [ 4654-39-1 ]

CAS No. :	4654-39-1	MDL No. :	MFCD00002897
Formula :	C₈H₉BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PMOSJSPFNDUAFY-UHFFFAOYSA-N
M.W :	201.06	Pubchem ID :	72851
Synonyms :

Calculated chemistry of [ 4654-39-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.08
TPSA :	20.23 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.07
Log Po/w (XLOGP3) :	1.47
Log Po/w (WLOGP) :	1.98
Log Po/w (MLOGP) :	2.61
Log Po/w (SILICOS-IT) :	2.68
Consensus Log Po/w :	2.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.32
Solubility :	0.952 mg/ml ; 0.00474 mol/l
Class :	Soluble
Log S (Ali) :	-1.5
Solubility :	6.34 mg/ml ; 0.0315 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.49
Solubility :	0.0652 mg/ml ; 0.000324 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.16

Safety of [ 4654-39-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4654-39-1 ]

* 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 [ 4654-39-1 ]
Downstream synthetic route of [ 4654-39-1 ]

[ 4654-39-1 ] 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,

[ 4654-39-1 ] Synthesis Path-Downstream 1~6

1
[ 4654-39-1 ]
[ 46112-46-3 ]

Reference： [1]Journal of the American Chemical Society,1948,vol. 70,p. 4177

2
[ 109-72-8 ]
[ 60-29-7 ]
[ 124-38-9 ]
[ 4654-39-1 ]
[ 46112-46-3 ]

Reference： [1]Journal of the American Chemical Society,1948,vol. 70,p. 4177

3
[ 4654-39-1 ]
[ 214360-70-0 ]
[ 876915-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 60℃;	The starting material, 2-(4-(thiophen-3-yl)phenyl)ethanol, was synthesized asfollows: In a sealed vessel was combined 2-(4-bromophenyl)ethanol (70 jxL), 4,4,5,5-tetramethyl-2-(thiophen-3-yl)-l,3,2-dioxaborolane (126 mg), K2CO3 (207 mg), catalyticPd(PPh3)4, 4.5 mL THF, and 0.5 mL H2O. The vessel was heated in an oil bath at 60 Covernight. The reaction mixture was diluted with water and DCM. The organic layerwas concentrated to yield 2-(4-(thiophen-3-yl)phenyl)ethanol (80 mg) as a solid whiteproduct. 80 mg tert-butyl (S)-2-(4-(4-(thiophen-3-yl)phenethyloxy)phenylcarbamoyl)-l-hydroxypropan-2-ylcarbamate was synthesized following the general procedureemploying 2-(4-(thiophen-3-yl)phenyl)ethanol (200 mg), 7V-(Boc)-a-methylserine (175mg), HATU (375 mg), and DIPEA (430 uL). MS (ESI, M+Na+) = 519. 2.6 mg of thephosphate was then synthesized from the carbamate (40 mg) as a solid white solid. MS(ESI, M+H+) = 477; *H NMR (400 MHz, DMSO-d6) 5 9.96 (br s, 1H), 7.81 (m, 1H),7.65 (m, 3H), 7.5 (m, 3H), 7.3 (m, 2H), 6.9 (m, 2H), 4.28 (m, 1H), 4.17 (m, 2H), 4.06(m, 1H), 3.04 (t, 2H), 1.48 (s, 3H).

Reference： [1]Patent: WO2006/20951,2006,A1 .Location in patent: Page/Page column 126-127

4
[ 4654-39-1 ]
[ 131184-73-1 ]
[ 1194551-47-7 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 5154 - 5157

5
[ 827-99-6 ]
[ 4654-39-1 ]
1-(4-bromophenethyloxy)-3-(trifluoromethoxy)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.2%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 15.5h;	(1) 17.42 g (66.42 mmol) of triphenylphosphine was added at room temperature to a solution having 9.21 g (45.81 mmol) of 2-(4-bromophenyl)ethanol and 8.61 g (48.34 mmol) of <strong>[827-99-6]3-(trifluoromethoxy)phenol</strong> dissolved in 160 ml of THF, followed by stirring for 10 minutes. Then, 31.23 ml (68.41 mmol) of DEAD (2.2 M toluene solution) was dropwise added over a period of 20 minutes, followed by stirring further for 15 hours. The solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (developing solvent: heptane/ethyl acetate=98/2 to 95/5, volume ratio, the same applies hereinafter) to obtain 14.10 g (yield: 85.2percent) of 1-(4-bromophenethyloxy)-3-(trifluoromethoxy)benzene as a colorless oil. 1H-NMR(300 MHz, CDCl3, deltappm): 7.44(d, 2H, J=8.1 Hz), 7.26(dd, 1H, J=8.1 Hz, 8.1 Hz), 7.16(d, 2H, J=8.1 Hz), 6.81(d, 1H, J=8.1 Hz), 6.80(d, 1H, J=8.1 Hz), 6.75-6.71(br, 1H), 4.14(t, 2H, J=6.9 Hz), 3.05(t, 2H, J=6.9 Hz)

Reference： [1]Patent: US2016/192651,2016,A1 .Location in patent: Paragraph 0279

6
[ 3973-08-8 ]
[ 4654-39-1 ]
4-bromophenethyl thiazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.7%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 5h;	General procedure: 2.5mmol thiazole-4-carboxyli acid and 2.0mmol alcohol were dissolved in 25mL dichloromethane (DCM) in a dry flask with continuous stirring, followed by the addition of 2.5mmol 3-(3-dimethylaminopropyl) -1-ethylcarbodiimide hydrochloride. When the temperature of the reaction system cooled to 0°C, 0.2mmol 4-dimethylaminopyridine was added dropwise and reacted for 1hat 0°C. Then the temperature was elevated to room temperature for another 4h reaction. The reaction was stopped by adding 25mL saturated NaHCO3 solution and extracted twice with 20mL dichloromethane (2×20mL). The extracted organic layers were first dried by anhydrous Na2SO4, and then filtered and concentrated under vacuum distillation, obtaining the crude products. Finally, the crude products were further purified using column chromatography (ethy lacetate:petroleum ether, 1:5).

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 145,p. 64 - 73

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Technical Information

? Alkyl Halide Occurrence ? 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 ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Jones Oxidation ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? 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 Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Ritter Reaction ? Sharpless Olefin Synthesis ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Swern Oxidation ? Vilsmeier-Haack Reaction

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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. 4654-39-1 ] {[proInfo.proName]}

Quality Control of [ 4654-39-1 ]

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Product Details of [ 4654-39-1 ]

Calculated chemistry of [ 4654-39-1 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 4654-39-1 ]

Application In Synthesis of [ 4654-39-1 ]

[ 4654-39-1 ] Synthesis Path-Upstream 1~3

[ 4654-39-1 ] Synthesis Path-Downstream 1~6

Technical Information

Related Functional Groups of [ 4654-39-1 ]

Aryls

Bromides

Alcohols

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Physical hazards

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[ 4654-39-1 ]