59772-49-5

Basic information

• Product Name: Benzenamine, 2-bromo-6-chloro-
• Synonyms: 2-Bromo-6-chloroaniline;2-Bromo-6-chlorobenzenamine
• CAS NO: 59772-49-5
• Molecular Formula: C₆H₅BrClN
• Molecular Weight: 206.4676
• Mol File: 59772-49-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 57-58 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 242.8 °C at 760 mmHg
• Flash Point: 100.6 °C
• Appearance: /
• Density: 1.722 g/cm³
• Vapor Pressure: 0.0333mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform, Dichloromethane, Methanol
• PKA: 0.59±0.10(Predicted)
• CAS DataBase Reference: Benzenamine, 2-bromo-6-chloro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 2-bromo-6-chloro-(59772-49-5)
• EPA Substance Registry System: Benzenamine, 2-bromo-6-chloro-(59772-49-5)

Safety Data

• Hazardous Substances Data: 59772-49-5(Hazardous Substances Data)

Usage

Description

Benzenamine, 2-bromo-6-chloro-, also known as 2-Bromo-6-chloroaniline, is an organic compound derived from benzenamine with a bromine atom at the 2nd position and a chlorine atom at the 6th position. It is characterized by its chemical structure and properties, which make it a valuable intermediate in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
Benzenamine, 2-bromo-6-chlorois used as an intermediate in the synthesis of Diclofenac Monobromo Sodium Salt (D436490) for the pharmaceutical industry. Benzenamine, 2-bromo-6-chloroserves as a bromide impurity of Diclofenac (D436450), which is a nonsteroidal anti-inflammatory drug (NSAID) used to relieve pain and inflammation.

InChI:InChI=1/C6H5BrClN/c7-4-2-1-3-5(8)6(4)9/h1-3H,9H2

Synthetic route

2-bromo-6-chlorobenzoic acid (93224-85-2) → 2-Chloro-6-bromoaniline (59772-49-5)

Conditions	Yield
Stage #1: 2-bromo-6-chlorobenzoic acid With sulfuric acid at 60℃; for 1.5h; Stage #2: With sodium azide at 20℃; for 42h; Schmidt rearrangement; Stage #3: With ammonium hydroxide at 0℃;	92%

4-amino-3-bromo-5-chlorobenzenesulfonamide → 2-Chloro-6-bromoaniline (59772-49-5)

Conditions	Yield
With sulfuric acid at 150℃; for 2h; Temperature;	85%

2'-Chloro-6'-bromobenzanilide (90493-87-1) → 2-Chloro-6-bromoaniline (59772-49-5)

Conditions	Yield
With sulfuric acid for 3h; Heating;	66%

2-bromoaniline (615-36-1) → 2-Chloro-6-bromoaniline (59772-49-5) + 4-chloro-2-bromoaniline (873-38-1)

Conditions	Yield
With N-chloro-succinimide; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S,2S)-2-(mesitylselanyl)-2,3-dihydro-1H-inden-1-yl)thiourea In chloroform-d1 at 0℃; for 18h; regioselective reaction;	A 40% B n/a

2-Chloroaniline (95-51-2) → 2-Chloro-6-bromoaniline (59772-49-5) + 2-chloro-4-bromoaniline (38762-41-3)

Conditions	Yield
With dihydrogen peroxide; ammonium bromide; acetic acid at 20℃; for 2.5h;
Stage #1: o-chloroaniline With dihydrogen peroxide; acetic acid; potassium bromide In water at 20℃; for 3h; Stage #2: With sodium hydrogencarbonate In diethyl ether; water regioselective reaction;

N-(2-bromophenyl)hydroxylamine (35758-75-9) → 2-Chloro-6-bromoaniline (59772-49-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaHCO3 / diethyl ether; H2O / 1 h / T < 5 deg C; or in benzene 2: 71 percent / SOCl2 / diethyl ether / 1 h / T < 5 deg C 3: 66 percent / 70percent H2SO4 / 3 h / Heating View Scheme

N-(2-Bromo-phenyl)-N-hydroxy-benzamide (90493-81-5) → 2-Chloro-6-bromoaniline (59772-49-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / SOCl2 / diethyl ether / 1 h / T < 5 deg C 2: 66 percent / 70percent H2SO4 / 3 h / Heating View Scheme

2-Chloroaniline (95-51-2) → 2-Chloro-6-bromoaniline (59772-49-5) + 2-chloro-4,6-dibromoaniline (874-18-0) + 2-chloro-4-bromoaniline (38762-41-3)

Conditions	Yield
With bromine at 20 - 25℃; for 0.0333333h; pH=8.5 - 9; aq. buffer;

sulfanilamide (63-74-1) → 2-Chloro-6-bromoaniline (59772-49-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-chloro-succinimide / tetrahydrofuran / 25 h / 40 °C 2: N-Bromosuccinimide / acetonitrile / 3 h / 20 °C 3: sulfuric acid / 2 h / 150 °C View Scheme

2-Chloro-6-bromoaniline (59772-49-5) → 1-bromo-3-chloro-2-nitrobenzene (59772-48-4)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 70℃; for 2h;	94%
With trifluoroacetyl peroxide In dichloromethane at -5 - 5℃; for 2h;	75%

2-Chloro-6-bromoaniline (59772-49-5) + benzo[b]thiophen-3-yl-3-boronic acid (113893-08-6) → C14H10ClNS

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; toluene for 4h; Reflux;	91%

2-Chloro-6-bromoaniline (59772-49-5) + benzofurane-3-ylboronic acid → C14H10ClNO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; toluene for 4h; Reflux;	91%

3-chloro-4-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-N-(TIPS)pyrrole (1126425-82-8) + 2-Chloro-6-bromoaniline (59772-49-5) → 2-chloro-6-(4-chloro-1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline (1126425-92-0)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 35℃; for 12h; Suzuki-Miyaura coupling; Inert atmosphere;	82%

2-Chloro-6-bromoaniline (59772-49-5) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline (1126425-86-2)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 35℃; for 12h; Suzuki-Miyaura coupling; Inert atmosphere;	82%

methyl (S)-2-((tert-butoxycarbonyl)amino)-5-(triethylsilyl)pent-4-ynoate (1152312-10-1) + 2-Chloro-6-bromoaniline (59772-49-5) → C23H35ClN2O4Si

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); N-Methyldicyclohexylamine In 1,4-dioxane at 60℃; for 36h; Inert atmosphere; Sealed tube;	82%

2-Chloro-6-bromoaniline (59772-49-5) + phenylboronic acid (98-80-6) → 3-chloro-[1,1'-biphenyl]-2-amine (76838-82-9)

Conditions	Yield
Stage #1: 2-bromo-6-chloroaniline; phenylboronic acid With potassium carbonate In 1,4-dioxane; water for 0.166667h; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water for 1h;	81.1%

2-Chloro-6-bromoaniline (59772-49-5) + 2-Biphenylboronic acid (4688-76-0) → C18H14ClN

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; water; toluene at 100℃; for 15h;	80%

iodobenzene (591-50-4) + 2-Chloro-6-bromoaniline (59772-49-5) → C18H13BrClN

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 4h; Inert atmosphere; Reflux;	70%

2-Chloro-6-bromoaniline (59772-49-5) + potassium vinyltrifluoroborate → 2-chloro-6-vinylaniline

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In tetrahydrofuran; water at 80℃; for 9h;	56%

2-Chloro-6-bromoaniline (59772-49-5) + chloroacetyl chloride (79-04-9) → chloro-acetic acid-(2-bromo-6-chloro-anilide)

2-Chloro-6-bromoaniline (59772-49-5) → N,N-diethyl-glycine-(2-bromo-6-chloro-anilide) (100140-98-5)

2-Chloro-6-bromoaniline (59772-49-5) → methyl 2-vinyl-6-chloroaniline-N-carboxylate

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / tetrahydrofuran; water / 9 h / 80 °C 2: pyridine / dichloromethane / 0 - 25 °C View Scheme

2-Chloro-6-bromoaniline (59772-49-5) → methyl 7-chloro-indole-1-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / tetrahydrofuran; water / 9 h / 80 °C 2: pyridine / dichloromethane / 0 - 25 °C 3: bis(benzonitrile)palladium(II) dichloride; tert.-butylnitrite; oxygen / tert-butyl alcohol / 15 h / 70 °C / 760.05 Torr / Schlenk technique View Scheme

2-Chloro-6-bromoaniline (59772-49-5) → 7-chloro-1H-indole (53924-05-3)

Conditions

Yield

Multi-step reaction with 4 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / tetrahydrofuran; water / 9 h / 80 °C 2: pyridine / dichloromethane / 0 - 25 °C 3: bis(benzonitrile)palladium(II) dichloride; tert.-butylnitrite; oxygen / tert-butyl alcohol / 15 h / 70 °C / 760.05 Torr / Schlenk technique 4: potassium hydroxide / methanol / 1 h / Reflux View Scheme

2-Chloro-6-bromoaniline (59772-49-5) → 7-(o-tolyl)-1H-indole (1073494-35-5)

Conditions

Yield

Multi-step reaction with 5 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / tetrahydrofuran; water / 9 h / 80 °C 2: pyridine / dichloromethane / 0 - 25 °C 3: bis(benzonitrile)palladium(II) dichloride; tert.-butylnitrite; oxygen / tert-butyl alcohol / 15 h / 70 °C / 760.05 Torr / Schlenk technique 4: potassium hydroxide / methanol / 1 h / Reflux 5: palladium diacetate; potassium phosphate; ruphos / tetrahydrofuran; toluene / 22 h / 100 °C / Schlenk technique; Inert atmosphere View Scheme

2-Chloro-6-bromoaniline (59772-49-5) → C21H12ClNO

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / toluene; ethanol / 4 h / Reflux 2: triethylamine / 0 °C 3: trichlorophosphate / nitrobenzene / 12 h / 150 °C View Scheme

2-Chloro-6-bromoaniline (59772-49-5) → C27H24BNO3

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / toluene; ethanol / 4 h / Reflux 2: triethylamine / 0 °C 3: trichlorophosphate / nitrobenzene / 12 h / 150 °C 4: potassium acetate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / 1,4-dioxane / 12 h / Reflux View Scheme

2-Chloro-6-bromoaniline (59772-49-5) → C54H33N5S

Conditions

Yield

Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / toluene; ethanol / 4 h / Reflux 2: triethylamine / 0 °C 3: trichlorophosphate / nitrobenzene / 12 h / 150 °C 4: potassium acetate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / 1,4-dioxane / 12 h / Reflux 5: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 12 h / Reflux View Scheme

2-Chloro-6-bromoaniline (59772-49-5) → C54H32N4S

Conditions

Yield

Multi-step reaction with 6 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / toluene; ethanol / 4 h / Reflux 2: triethylamine / 0 °C 3: trichlorophosphate / nitrobenzene / 12 h / 150 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / Reflux 5: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 5 h / Reflux 6: tris-(dibenzylideneacetone)dipalladium(0); XPhos; potassium phosphate / 1,4-dioxane / 12 h / Reflux View Scheme

Upstream product

• 90493-87-1 2'-Chloro-6'-bromobenzanilide 
• 95-51-2 o-chloroaniline 
• 63-74-1 sulfanilamide 
• 615-36-1 2-bromoaniline 
• 93224-85-2 2-bromo-6-chlorobenzoic acid 
• 90493-81-5 N-(2-Bromo-phenyl)-N-hydroxy-benzamide 
• 35758-75-9 N-(2-bromophenyl)hydroxylamine 

Downstream Products

• 100140-98-5 N,N-diethyl-glycine-(2-bromo-6-chloro-anilide) 
• 1126425-92-0 2-chloro-6-(4-chloro-1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline 
• 59772-48-4 1-bromo-3-chloro-2-nitrobenzene 
• 1126425-86-2 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline 
• 53924-05-3 7-chloro-1H-indole 
• 1073494-35-5 7-(o-tolyl)-1H-indole 

Relevant articles and documents

Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst

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Selective oxidation of sulfides and oxidative bromination of organic substrates catalyzed by polymer anchored Cu(II) complex

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