29270-30-2

Basic information

• Product Name: 2-Bromo-2-(2'-chlorophenyl) acetic acid
• Synonyms: A-BROMO 2-CHLOROPHENYLACETIC ACID;alpha-Bromo-2-chlorobenzeneacetic acid;2-BROMO-2-(2'-CHLOROPHENYL) ACETIC ACID;à-bromo-2-chlorophenylacetic acid;A-BROMO-2-CHLOROBENZENEACETIC ACID;L-ALPHA-BROMO-(2-CHLORO)PHENYL ACETIC ACID;α-Bromo-2-chlorobenzeneacetic acid;ɑ-Bromo-2-chlorophenylacetic acid, 98%
• CAS NO: 29270-30-2
• Molecular Formula: C₈H₆BrClO₂
• Molecular Weight: 249.49
• Product Categories: Pharmaceutical Intermediates
• Mol File: 29270-30-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 105-108°C
• Boiling Point: 316.7 °C at 760 mmHg
• Flash Point: 145.3 °C
• Appearance: /
• Density: 1.747 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol
• PKA: 2.24±0.10(Predicted)
• CAS DataBase Reference: 2-Bromo-2-(2'-chlorophenyl) acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-2-(2'-chlorophenyl) acetic acid(29270-30-2)
• EPA Substance Registry System: 2-Bromo-2-(2'-chlorophenyl) acetic acid(29270-30-2)

Safety Data

• Hazard Codes: C,Xi
• Statements: 36/37/38
• Safety Statements: 24/25
• RIDADR: UN3261
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 29270-30-2(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

2-Bromo-2-(2-chlorophenyl)acetic Acid is used as an intermediate in the preparation of biologically active compounds such as the antithrombotic Clopidogrel (C587250).

Synthetic route

2'-chloro-benzeneacetic acid (2444-36-2) → α-bromo-2-chlorophenyl acetic acid (29270-30-2)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide; sodium bromide In dichloromethane; water at 10 - 30℃; for 40h; Time; Large scale;	89%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 80℃; for 5h;	48%
With N-Bromosuccinimide In tetrachloromethane
With N-Bromosuccinimide
With sulfuric acid; dihydrogen peroxide; sodium bromide In dichloromethane at 25℃; for 24h; Reagent/catalyst; Solvent; Irradiation;

2-amino-(2-chlorophenyl)ethanoic acid (86169-24-6, 141196-64-7, 141315-50-6, 88744-36-9) → α-bromo-2-chlorophenyl acetic acid (29270-30-2)

Conditions	Yield
With hydrogen bromide; sodium nitrite In water at 0℃; for 7.33333h;	73%
Stage #1: 2-amino-(2-chlorophenyl)ethanoic acid With hydrogen bromide In water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In water at 0 - 20℃; for 3.5h;

Bromoform (75-25-2) + 2-chloro-benzaldehyde (89-98-5) → α-bromo-2-chlorophenyl acetic acid (29270-30-2)

Conditions	Yield
With hydrogenchloride; potassium hydroxide In 1,2-dimethoxyethane; water; toluene	67%
Stage #1: Bromoform; 2-chloro-benzaldehyde With potassium hydroxide In 1,2-dimethoxyethane; water at -5 - 10℃; for 13h; Stage #2: With hydrogenchloride In dichloromethane; water

2-chloromandelic acid (10421-85-9, 52923-23-6, 52950-18-2, 52950-19-3) → α-bromo-2-chlorophenyl acetic acid (29270-30-2)

Conditions	Yield
With hydrogen bromide at 120℃; unter Druck;

2'-chloro-benzeneacetic acid (2444-36-2) → 2-bromo-2-(4-fluorophenyl)acetic acid (29270-33-5) + α-bromo-2-chlorophenyl acetic acid (29270-30-2)

Bromoform (75-25-2) + di-isopropyl ether (108-20-3) + 2-chloro-benzaldehyde (89-98-5) → α-bromo-2-chlorophenyl acetic acid (29270-30-2)

Conditions	Yield
With hydrogenchloride; potassium hydroxide In 1,4-dioxane; water; toluene

methanol (67-56-1) + α-bromo-2-chlorophenyl acetic acid (29270-30-2) → methyl 2-bromo-2-(2-chlorophenyl)acetate (85259-19-4)

Conditions	Yield
With sulfuric acid for 3h; Reflux;	95.07%
With sulfuric acid at 25 - 66℃;	93%
With sulfuric acid at 75℃; Time; Large scale;	90%

4,5,6,7-tetrahydrothieno[3,2-c]pyridine (54903-50-3) + α-bromo-2-chlorophenyl acetic acid (29270-30-2) → 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetic acid (90055-55-3)

Conditions	Yield
In acetonitrile at 20℃;	91%
With triethylamine In dichloromethane for 5h; Product distribution / selectivity; Heating / reflux;	78%

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride (28783-41-7) → 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridine-5(4H)-yl)acetic acid (90055-55-3)

Conditions	Yield
Stage #1: α-bromo-2-chlorophenyl acetic acid; 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride With potassium hydroxide In methanol; water at 10 - 40℃; for 3h; Stage #2: With hydrogenchloride In methanol; water at 5 - 20℃; for 4h; pH=3.5;	88%
Stage #1: α-bromo-2-chlorophenyl acetic acid; 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride With potassium hydroxide In methanol; water at 15 - 40℃; for 3h; Stage #2: With hydrogenchloride In methanol; water at 20℃; for 2h; pH=3.5;	88%
Stage #1: 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride With sodium hydroxide In water at 20 - 35℃; Stage #2: α-bromo-2-chlorophenyl acetic acid In water at 20 - 27℃; Stage #3: With hydrogenchloride In water; ethyl acetate at 20 - 30℃; pH=3.5 - 4.5;
With potassium hydroxide In water at 0 - 20℃; for 24h;	12 g

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 2-bromo-2-(2-chlorophenyl)acetate (85259-19-4)

Conditions	Yield
In methanol; toluene for 0.25h; Inert atmosphere; Cooling in water bath;	86%

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + [1,2,4]triazolo[4',3':1,5][1,2,4]triazolo[4,3-c]thieno-[2,3-e]pyrimidine-9(8H)-thione (1639056-04-4) → 2-([1,2,4]triazolo[4',3':1,5][1,2,4]triazolo[4,3-c]thieno-[2,3-e]pyrimidin-9-ylthio)-2-(2-chlorophenyl)acetic acid (1639056-06-6)

Conditions	Yield
Stage #1: [1,2,4]triazolo[4',3':1,5][1,2,4]triazolo[4,3-c]thieno-[2,3-e]pyrimidine-9(8H)-thione With sodium acetate In ethanol at 20℃; for 0.0833333h; Stage #2: α-bromo-2-chlorophenyl acetic acid In ethanol for 6h; Reflux;	82%

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + [1,2,4]triazolo[4',3':1,5][1,2,4]triazolo[4,3-c]thieno-[3,2-e]pyrimidine-9(8H)-thione (1639055-95-0) → 2-([1,2,4]triazolo[4',3':1,5][1,2,4]triazolo[4,3-c]thieno-[3,2-e]pyrimidin-9-ylthio)-2-(2-chlorophenyl)acetic acid (1639055-97-2)

Conditions	Yield
Stage #1: [1,2,4]triazolo[4',3':1,5][1,2,4]triazolo[4,3-c]thieno-[3,2-e]pyrimidine-9(8H)-thione With sodium acetate In ethanol at 20℃; for 0.0833333h; Stage #2: α-bromo-2-chlorophenyl acetic acid In ethanol for 6h; Reflux;	78%

thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine-3(2H)-thione (1262236-28-1) + α-bromo-2-chlorophenyl acetic acid (29270-30-2) → 2-chlorophenyl(thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidin-3-ylthio)acetic acid

Conditions	Yield
Stage #1: thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine-3(2H)-thione With sodium acetate In ethanol at 20℃; for 0.0833333h; Stage #2: α-bromo-2-chlorophenyl acetic acid In ethanol for 6h; Reflux;	71%

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + thiourea (17356-08-0) → 5-(2-chlorophenyl)-2-imino-1,3-thiazolidin-4-one (85259-20-7)

Conditions	Yield
With hydrogen bromide at 20℃; for 24h;	66%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + α-bromo-2-chlorophenyl acetic acid (29270-30-2) → (2-chlorophenyl)-(3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid (1552304-62-7)

Conditions	Yield
In acetonitrile at 20℃;	50%

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol (24155-42-8) → 2-(2-chlorophenyl)-2-(1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy)acetic acid

Conditions	Yield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.333333h; Inert atmosphere; Stage #2: α-bromo-2-chlorophenyl acetic acid In N,N-dimethyl-formamide; mineral oil at 20℃; for 24h; Inert atmosphere;	41%

2-Vinylnaphthalene (827-54-3) + α-bromo-2-chlorophenyl acetic acid (29270-30-2) → C20H15ClO2

Conditions	Yield
With cobalt(II) nitrate hexahydrate; 2,2,6,6-tetramethylheptane-3,5-dione; potassium carbonate; N,N-dimethyl-formamide at 140℃; for 24h;	39%

1-methyl-piperazine (109-01-3) + α-bromo-2-chlorophenyl acetic acid (29270-30-2) → (+/-)-(2-chlorophenyl)(4-methyl-1-piperazinyl)acetic acid hydrochloride (1092477-37-6)

Conditions	Yield
Stage #1: 1-methyl-piperazine; α-bromo-2-chlorophenyl acetic acid With potassium carbonate In tetrahydrofuran at 20℃; Stage #2: With hydrogenchloride; water	36%

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + 1-amino-9,10-anthracenedione (82-45-1) → (2-chloro-phenyl)-(9,10-dioxo-9,10-dihydro-[1]anthrylamino)-acetic acid

Conditions	Yield
With sodium acetate at 180℃;

ethyl N-hydroxylcarbamate (589-41-3) + α-bromo-2-chlorophenyl acetic acid (29270-30-2) → α--2-chlor-phenylessigsaeure (4718-69-8)

Conditions	Yield
With sodium ethanolate

α-bromo-2-chlorophenyl acetic acid (29270-30-2) → azido-(2-chloro-phenyl)-acetic acid (3380-96-9)

Conditions	Yield
With sodium azide; sodium carbonate In acetone

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + 4-chlorobenzaldehyde (104-88-1) + thiosemicarbazide (79-19-6) → 4-chloro-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone (133192-64-0)

Conditions	Yield
(i) , (ii) /BRN= 2099266/; Multistep reaction;

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + 2-chloro-benzaldehyde (89-98-5) + thiosemicarbazide (79-19-6) → 2-chloro-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone (133192-66-2)

Conditions	Yield
(i) , (ii) /BRN= 2099266/; Multistep reaction;

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + benzaldehyde (100-52-7) + thiosemicarbazide (79-19-6) → benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone (133192-62-8)

Conditions	Yield
(i) , (ii) /BRN= 2099266/; Multistep reaction;

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + 4-hydroxy-benzaldehyde (123-08-0) + thiosemicarbazide (79-19-6) → 4-hydroxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone

Conditions	Yield
(i) , (ii) /BRN= 2099266/; Multistep reaction;

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + 4-methoxy-benzaldehyde (123-11-5) + thiosemicarbazide (79-19-6) → 4-methoxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone (108897-02-5)

Conditions	Yield
(i) , (ii) /BRN= 2099266/; Multistep reaction;

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + salicylaldehyde (90-02-8) + thiosemicarbazide (79-19-6) → 2-hydroxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone (133192-60-6)

Conditions	Yield
(i) , (ii) /BRN= 2099266/; Multistep reaction;

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + 2,4-dichlorobenzaldeyhde (874-42-0) + thiosemicarbazide (79-19-6) → 2,4-dichloro-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone (132465-89-5)

Conditions	Yield
(i) , (ii) /BRN= 2099266/; Multistep reaction;

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + thiosemicarbazide (79-19-6) + 2-methylphenyl aldehyde (529-20-4) → 2-methyl-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone (108897-90-1)

Conditions	Yield
(i) , (ii) /BRN= 2099266/; Multistep reaction;

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + thiosemicarbazide (79-19-6) + ortho-anisaldehyde (135-02-4) → 2-methoxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone (108897-94-5)

Conditions	Yield
(i) , (ii) /BRN= 2099266/; Multistep reaction;

α-bromo-2-chlorophenyl acetic acid (29270-30-2) + thiosemicarbazide (79-19-6) + 4-dimethylamino-benzaldehyde (100-10-7) → 4-dimethylamino-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone (133296-82-9)

Conditions	Yield
(i) , (ii) /BRN= 2099266/; Multistep reaction;

Upstream product

• 2444-36-2 2'-chloro-benzeneacetic acid 
• 75-25-2 Bromoform 
• 108-20-3 di-isopropyl ether 
• 89-98-5 2-chloro-benzaldehyde 
• 86169-24-6 2-amino-(2-chlorophenyl)ethanoic acid 
• 10421-85-9 2-chloromandelic acid 

Downstream Products

• 133192-64-0 4-chloro-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 133192-66-2 2-chloro-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 133192-62-8 benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 108897-02-5 4-methoxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 133192-60-6 2-hydroxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 132465-89-5 2,4-dichloro-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 108897-90-1 2-methyl-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 108897-94-5 2-methoxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 133296-82-9 4-dimethylamino-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 133296-84-1 5-chloro-2-hydroxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 1070803-88-1 C₁₅H₁₃BrClNOS 
• 1552304-62-7 (2-chlorophenyl)-(3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid 
• 1639055-97-2 2-([1,2,4]triazolo[4',3':1,5][1,2,4]triazolo[4,3-c]thieno-[3,2-e]pyrimidin-9-ylthio)-2-(2-chlorophenyl)acetic acid 
• 1639056-06-6 2-([1,2,4]triazolo[4',3':1,5][1,2,4]triazolo[4,3-c]thieno-[2,3-e]pyrimidin-9-ylthio)-2-(2-chlorophenyl)acetic acid 

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