[ CAS No. 150529-73-0 ] {[proInfo.proName]}

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Quality Control of [ 150529-73-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 150529-73-0 ]

SDS Specification

Alternatived Products of [ 150529-73-0 ]

Product Details of [ 150529-73-0 ]

CAS No. :	150529-73-0	MDL No. :	MFCD06858764
Formula :	C₉H₉BrO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	ULSSGHADTSRELG-UHFFFAOYSA-N
M.W :	229.07	Pubchem ID :	11746402
Synonyms :

Calculated chemistry of [ 150529-73-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.01
TPSA :	26.3 ?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) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.44
Log Po/w (XLOGP3) :	2.7
Log Po/w (WLOGP) :	2.16
Log Po/w (MLOGP) :	2.7
Log Po/w (SILICOS-IT) :	2.71
Consensus Log Po/w :	2.54

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.13
Solubility :	0.169 mg/ml ; 0.000736 mol/l
Class :	Soluble
Log S (Ali) :	-2.91
Solubility :	0.285 mg/ml ; 0.00124 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.74
Solubility :	0.0419 mg/ml ; 0.000183 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.71

Safety of [ 150529-73-0 ]

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 [ 150529-73-0 ]

* 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 [ 150529-73-0 ]
Downstream synthetic route of [ 150529-73-0 ]

[ 150529-73-0 ] Synthesis Path-Upstream 1~3

1
[ 150529-73-0 ]
[ 2084-13-1 ]

Reference： [1] Patent: WO2013/52110, 2013, A1,

2
[ 150529-73-0 ]
[ 74-88-4 ]
[ 80622-53-3 ]

Yield	Reaction Conditions	Operation in experiment
82.3%	Stage #1: With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5 h; Inert atmosphere Stage #2: at 20℃; for 3 h; Inert atmosphere	To a dry 100 mL three-necked flask was added methyl 3-bromophenylacetate (4.58 g, 20 mmol, 1.0 eq) under N2.Add anhydrous tetrahydrofuran (30 mL),A 2.0 M solution of lithium diisopropylamide in THF / heptane / ethylbenzene (10.5 mL, 21 mmol, 1.05 eq) was slowly added dropwise at -78 °C.After the completion of the dropwise addition, the mixture was stirred for 30 minutes, and then methyl iodide (2.84 g, 20 mmol,1.0eq). Stirring was continued at room temperature for a further 3 hours.60 mL of water was added to the reaction flask, followed by extraction with 50 mL of dichloromethane, and the mixture was separated.The aqueous phase was extracted twice more with 30 mL of dichloromethane. Combine the organic phase,Wash twice with saturated saline solution,Drying with anhydrous sodium sulfate, concentration, and the residue was separated by column chromatography.Methyl 2-(3-bromophenyl)propanoate 3.95 g was obtained in a yield of 82.3percent.

Reference： [1] Patent: CN108794319, 2018, A, . Location in patent: Paragraph 0033-0035
[2] Green Chemistry, 2017, vol. 19, # 20, p. 4798 - 4803
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 11, p. 3299 - 3311

3
[ 67-56-1 ]
[ 150529-73-0 ]
[ 80622-53-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 21, p. 3373 - 3380

[ 150529-73-0 ] Synthesis Path-Downstream 1~4

1
[ 150529-73-0 ]
[ 71420-95-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2647 - 2652

2
[ 150529-73-0 ]
[ 74-88-4 ]
[ 80622-53-3 ]

Yield	Reaction Conditions	Operation in experiment
82.3%		To a dry 100 mL three-necked flask was added methyl 3-bromophenylacetate (4.58 g, 20 mmol, 1.0 eq) under N2.Add anhydrous tetrahydrofuran (30 mL),A 2.0 M solution of lithium diisopropylamide in THF / heptane / ethylbenzene (10.5 mL, 21 mmol, 1.05 eq) was slowly added dropwise at -78 C.After the completion of the dropwise addition, the mixture was stirred for 30 minutes, and then methyl iodide (2.84 g, 20 mmol,1.0eq). Stirring was continued at room temperature for a further 3 hours.60 mL of water was added to the reaction flask, followed by extraction with 50 mL of dichloromethane, and the mixture was separated.The aqueous phase was extracted twice more with 30 mL of dichloromethane. Combine the organic phase,Wash twice with saturated saline solution,Drying with anhydrous sodium sulfate, concentration, and the residue was separated by column chromatography.Methyl 2-(3-bromophenyl)propanoate 3.95 g was obtained in a yield of 82.3%.
		(3-Bromophenyl)acetic acid 11 (5.0 g, 23.3 mmol) and methanol (50 mL) were refluxed for 3 h in the presence of 0.2 mL of concentrated hydrochloric acid (HCl) to give the methyl (3-bromophenyl)acetate. After neutralization with saturated NaHCO3 and washing with brine, a pure product was obtained from the diethyl ether extract. This methyl acetate (4.9 g, 21.4 mmol) in dry THF (35 mL) was added dropwise to a stirred solution of 2.0 mol/L lithium diisopropylamide (LDA) (12.9 mL, 25.8 mmol) in THF/ethylbenzene/heptane at -78 C under argon (Ar), and after 30 min, iodomethane (CH3I) (2.0 mL, 32.2 mmol) was added slowly. The resulting solution was stirred for 5 h with the temperature changed from -78 to -40 C, then evaporated to dryness, and extracted with CH2Cl2 (50 mL). Evaporation of the solvent and purification of the residue by silica gel chromatography (n-hexane/AcOEt, 20:1) yielded the title compound as a colorless liquid (77.2%). 1H NMR (CDCl3) delta: 1.49 (3H, d, J = 7.1 Hz, alpha-CH3), 3.67 (3H, s, CO2CH3), 3.68 (1H, q, J = 7.1 Hz, CH), 7.18 (1H, t, J = 7.5 Hz, Ar-H5), 7.23 (1H, dt, J = 7.8, 1.7 Hz, Ar-H6), 7.38 (1H, dt, J = 7.3, 1.8 Hz, Ar-H4), 7.44 (1H, st, J = 1.7 Hz, Ar-H2). FAB-MS (m/z): 243.02 (M++H, calcd for C10H1279BrO2: 243.00).

Reference： [1]Patent: CN108794319,2018,A .Location in patent: Paragraph 0033-0035
[2]Green Chemistry,2017,vol. 19,p. 4798 - 4803
[3]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3299 - 3311

3
[ 67-56-1 ]
[ 150529-73-0 ]
[ 80622-53-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 3373 - 3380

4
[ 150529-73-0 ]
[ 60312-83-6 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In methanol; at 20℃; for 18h;	(3-Bromo-phenyl) -acetic acid methyl ester (15.33 g, 66.90 mmol) is dissolved in methanol [(50] ml) and ammonium hydroxide (100 ml). The reaction mixture is stirred at room temperature. The reaction is shown to be complete by TLC after 18 hours. The methanol is removed in vacuo and the product precipitates out. The solid is filtered off, washed with water and dried to give the title compd. MS (ES+) [MLE] 214 [(MH+-BR79),] 216 [(MH+-BR8L).]

Reference： [1]Patent: WO2004/16601,2004,A1 .Location in patent: Page 32

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Isomers

Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Alkylbenzene ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

Historical Records

Related Functional Groups of
[ 150529-73-0 ]

Aryls

[ 41841-16-1 ]

Methyl 2-(4-bromophenyl)acetate

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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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[ CAS No. 150529-73-0 ] {[proInfo.proName]}

Quality Control of [ 150529-73-0 ]

Related Doc. of [ 150529-73-0 ]

Product Details of [ 150529-73-0 ]

Calculated chemistry of [ 150529-73-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 150529-73-0 ]

Application In Synthesis of [ 150529-73-0 ]

[ 150529-73-0 ] Synthesis Path-Upstream 1~3

[ 150529-73-0 ] Synthesis Path-Downstream 1~4

Technical Information

Related Functional Groups of [ 150529-73-0 ]

Aryls

Bromides

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 150529-73-0 ]