56961-77-4

Basic information

• Product Name: 1-Bromo-2,3-dichlorobenzene
• Synonyms: 2,3-DICHLOROBROMOBENZENE;2,3-DICHLORO-1-BROMOBENZENE;1-BROMO-2,3-DICHLOROBENZENE;Benzene, 1-bromo-2,3-dichloro-;1-Bromo-2,3-Dichlorobenzene,>98%;1-BROMO-2,3-DICHLOROBENZENE 98%;1,2-Dichloro-3-bromobenzene;1-Bromo-2,3-dichlorobenzene,99%
• CAS NO: 56961-77-4
• Molecular Formula: C₆H₃BrCl₂
• Molecular Weight: 225.9
• EINECS: 260-476-2
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Bromine Compounds;Chlorine Compounds;Aryl;C6;Halogenated Hydrocarbons
• Mol File: 56961-77-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 58-61 °C(lit.)
• Boiling Point: 243 °C765 mm Hg(lit.)
• Flash Point: 243°C
• Appearance: light yellow crystalline flakes
• Density: 1.6351 (rough estimate)
• Vapor Pressure: 0.0556mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: insoluble
• BRN: 2246806
• CAS DataBase Reference: 1-Bromo-2,3-dichlorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-2,3-dichlorobenzene(56961-77-4)
• EPA Substance Registry System: 1-Bromo-2,3-dichlorobenzene(56961-77-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-28A-24/25
• WGK Germany: 3
• Hazardous Substances Data: 56961-77-4(Hazardous Substances Data)

Usage

Uses

1-Bromo-2,3-dichlorobenzene is a reagent used in the preparation of selective nonpeptidic inhibitors of striatal-enriched protein tryosine phosphatase.

InChI:InChI=1/C6H3BrCl2/c7-4-2-1-3-5(8)6(4)9/h1-3H

Synthetic route

2,3-dichloroaniline (608-27-5) → 1-bromo-2,3-dichlorobenzene (56961-77-4)

Conditions	Yield
With hydrogen bromide; sodium nitrite; copper In water at 35 - 65℃; Product distribution / selectivity; Sandmeyer Reaction;	87.7%
With hydrogen bromide; sodium bromide; sodium nitrite; copper(I) bromide In water at 60 - 65℃; for 2.5h; Product distribution / selectivity; Sandmeyer Reaction;	84%
With hydrogen bromide; sodium bromide; sodium nitrite; copper(II) sulfate In water at 45 - 65℃; Product distribution / selectivity; Sandmeyer Reaction;	83%
With hydrogen bromide; sodium nitrite; copper(I) bromide In water at 45 - 65℃; Product distribution / selectivity; Sandmeyer Reaction;	80%

4-bromo-2,3-dichloro-phenylamine (56978-48-4) → 1-bromo-2,3-dichlorobenzene (56961-77-4)

N-(4-bromo-3-chlorophenyl)acetamide (22459-81-0) → 1-bromo-2,3-dichlorobenzene (56961-77-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: glacial acetic acid / durch Chlorierung 2: sulfuric acid; alcohol View Scheme

4-Bromo-2,3-dichloroacetanilide (113571-16-7) → 1-bromo-2,3-dichlorobenzene (56961-77-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; alcohol View Scheme

1-bromo-2,3-dichlorobenzene (56961-77-4) + bis-(2-chloroethyl)amine hydrochloride (821-48-7) → C10H11Cl4N

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,4-dioxane at 80℃; for 9h; Temperature; Inert atmosphere;	94.5%

1-bromo-2,3-dichlorobenzene (56961-77-4) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(2,3-dichlorophenyl)piperazine-1-carboxylate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; XPhos In acetonitrile at 100℃; for 6h; Inert atmosphere;	91.1%
Stage #1: 1-bromo-2,3-dichlorobenzene; 1-t-Butoxycarbonylpiperazine With caesium carbonate In 1-methyl-pyrrolidin-2-one Heating; Stage #2: With tris(dibenzylideneacetone)dipalladium (0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1-methyl-pyrrolidin-2-one at 70 - 110℃; for 4h;	80%

1-bromo-2,3-dichlorobenzene (56961-77-4) + N1,N1,N3-triphenylbenzene-1,3-diamine → N1-(2,3-dichlorophenyl)-N1,N3,N3-triphenyl-1,3-phenylenediamine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene for 3h; Reflux;	90%
With dichloro bis((p-dimethylaminophenyl)-ϖ-di-tert-butylphosphine)palladium(II); potassium tert-butylate In o-xylene at 90℃; for 2.5h;
With sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 90℃; for 2h; Inert atmosphere;	61.8g
With sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 90℃; for 2h; Inert atmosphere;	61.8 g
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 90℃; for 2h; Inert atmosphere;	61.8 g

1-bromo-2,3-dichlorobenzene (56961-77-4) + C26H24N2O → C32H26Cl2N2O

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene for 3h; Reflux;	90%

1-bromo-2,3-dichlorobenzene (56961-77-4) + 3-chloro-10H-spiro[acridine-9,9'-xanthene] → C31H18Cl3NO

Conditions	Yield
With 2-(benzothiophen-2-yl)pyridine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 180℃; for 12h;	89%

1-bromo-2,3-dichlorobenzene (56961-77-4) + 4-(1-phenyl-1H-benzoimidazol-2-yl)-aniline (65847-34-9) → C25H17Cl2N3

Conditions	Yield
With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 1h; Inert atmosphere;	88%
With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 1h; Inert atmosphere;	88%

1-bromo-2,3-dichlorobenzene (56961-77-4) + C21H19N3 → C27H21Cl2N3

Conditions	Yield
With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 1h; Inert atmosphere;	87%
With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 1h; Inert atmosphere;	87%

1-bromo-2,3-dichlorobenzene (56961-77-4) + diphenylamine (122-39-4) → 2,3-dichloro-N,N-diphenylaniline

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In toluene at 110℃; Inert atmosphere;	84%
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 80℃; for 2h; Inert atmosphere;	80%
With tetrabutoxytitanium; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 180℃; for 12h;	57%

1-bromo-2,3-dichlorobenzene (56961-77-4) + (2,6-dimethoxyphenyl)boronic acid (23112-96-1) → 2,3-dichloro-2',6'-dimethoxy-1,1'-biphenyl

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 90℃; for 2h;	83%

1-bromo-2,3-dichlorobenzene (56961-77-4) + C39H30N2S → C45H32Cl2N2S

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 90℃; for 12h; Inert atmosphere;	82.6%

1-bromo-2,3-dichlorobenzene (56961-77-4) + phenylboronic acid (98-80-6) → 2,3-dichlorobiphenyl (16605-91-7)

Conditions	Yield
With potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 0.5h;	82%
With (R,R)-N,N'-bis[(2-fluorophenyl)methyl]-1,2-cyclohexanediamine PdCl2 complex; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 24h; Suzuki coupling; Aerobic conditions;	51%

di-tert-butyl dicarbonate (24424-99-5) + 1-bromo-2,3-dichlorobenzene (56961-77-4) → tert-butyl 2,3-dichlorobenzoate (1018948-94-1)

Conditions	Yield
Stage #1: 1-bromo-2,3-dichlorobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -10℃; Stage #3: With citric acid In tetrahydrofuran; hexane; toluene Further stages.;	80%
Stage #1: 1-bromo-2,3-dichlorobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃; for 1h; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -10℃; for 2h; Inert atmosphere;	80%

4-(pyridin-2-yl)aniline (18471-73-3) + 1-bromo-2,3-dichlorobenzene (56961-77-4) → C17H12Cl2N2

Conditions	Yield
With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 1h;	80%

1-bromo-2,3-dichlorobenzene (56961-77-4) + C22H21N3 → C28H23Cl2N3

Conditions	Yield
With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 1h; Inert atmosphere;	80%
With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 110℃; for 1h; Inert atmosphere;	80%

1-bromo-2,3-dichlorobenzene (56961-77-4) + C31H20N2 → C37H22Cl2N2

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 12h;	77%

piperazine (110-85-0) + di-tert-butyl dicarbonate (24424-99-5) + 1-bromo-2,3-dichlorobenzene (56961-77-4) → tert-butyl 4-(2,3-dichlorophenyl)piperazine-1-carboxylate

Conditions	Yield
Stage #1: piperazine; 1-bromo-2,3-dichlorobenzene With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 60 - 70℃; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In dichloromethane; toluene at 20℃;	76%

C13H12NO2(1+)*Cl(1-) (948838-40-2) + 1-bromo-2,3-dichlorobenzene (56961-77-4) → (4-(2,3-dichlorophenyl)pyridin-1(4H)-yl)(phenyl)methanone

Conditions	Yield
Stage #1: 1-bromo-2,3-dichlorobenzene With isopropylmagnesium bromide In tetrahydrofuran at -30 - -20℃; Stage #2: C13H12NO2(1+)*Cl(1-) at 0 - 20℃;	76%

1-bromo-2,3-dichlorobenzene (56961-77-4) + aniline (62-53-3) → 2-chloro-N,N’-diphenyl-1,3-benzenediamine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 72h; Inert atmosphere; chemoselective reaction;	76%
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In toluene for 6h; Reflux; Inert atmosphere;	75%
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In toluene for 6h; Inert atmosphere; Reflux;	75%
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 26h; Buchwald-Hartwig Coupling; Inert atmosphere;	63%
Stage #1: 1-bromo-2,3-dichlorobenzene With sodium t-butanolate In toluene for 1h; Reflux; Stage #2: aniline With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene Heating;	50%

1-bromo-2,3-dichlorobenzene (56961-77-4) + diphenylamine (122-39-4) → 2-chloro-N1,N1,N3,N3-tetraphenylbenzene-1,3-diamine

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate In toluene for 3h; Reflux;	75.8%
With dichloro bis((p-dimethylaminophenyl)-ϖ-di-tert-butylphosphine)palladium(II); potassium tert-butylate In o-xylene at 80 - 120℃; for 5h;	66%
With sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 80 - 120℃; for 5h; Inert atmosphere;	65 g
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 80 - 120℃; for 5h;	65 g

[1,4]diazepine-1-carboxylic acid tert-butyl ester + 1-bromo-2,3-dichlorobenzene (56961-77-4) → 1-(2,3-dichlorophenyl)-[1,4]diazepine hydrochloride salt

Conditions	Yield
Stage #1: [1,4]diazepine-1-carboxylic acid tert-butyl ester; 1-bromo-2,3-dichlorobenzene With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene for 8h; Heating / reflux; Stage #2: With hydrogenchloride In ethyl acetate at 10℃;	75%

bis(4-tert-butylphenyl)amine (4627-22-9) + 1-bromo-2,3-dichlorobenzene (56961-77-4) → N1,N1,N3,N3-tetrakis(4-(tert-butyl)phenyl)-2-chlorobenzene-1,3-diamine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In toluene at 90℃; for 5h; Inert atmosphere;	75%

1-bromo-2,3-dichlorobenzene (56961-77-4) + C31H29NO → C37H31Cl2NO

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 5h; Reflux;	75%

4,7-diaza-spiro[2,5]octane-4-carboxylic acid tert-butyl ester (674792-08-6) + 1-bromo-2,3-dichlorobenzene (56961-77-4) → tert-butyl 7-(2,3-dichlorophenyl)-4,7-diazaspiro[2.5]octane-4-carboxylate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 90℃; Inert atmosphere;	74%

4-tert-Butylaniline (769-92-6) + 1-bromo-2,3-dichlorobenzene (56961-77-4) → C16H17Cl2N

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 90℃; for 10h;	73%

1-bromo-2,3-dichlorobenzene (56961-77-4) + aniline (62-53-3) → 2,3-Dichlor-diphenylamin (105837-54-5)

Conditions	Yield
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 24h; Reflux;	71.2%

1,4-Diazacycloheptane (505-66-8) + di-tert-butyl dicarbonate (24424-99-5) + 1-bromo-2,3-dichlorobenzene (56961-77-4) → tert-butyl 4-(2,3-dichlorophenyl)-1,4-diazepane-1-carboxylate (1354030-12-8)

Conditions	Yield
Stage #1: 1,4-Diazacycloheptane; 1-bromo-2,3-dichlorobenzene With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 60 - 70℃; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In dichloromethane; toluene at 20℃;	70%
Stage #1: 1,4-Diazacycloheptane; 1-bromo-2,3-dichlorobenzene With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 80℃; for 24h; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In toluene at 20℃; for 2h; Inert atmosphere;

3,6-di(tert-butyl)-9H-carbazole (37500-95-1) + 1-bromo-2,3-dichlorobenzene (56961-77-4) → C46H51ClN2

Conditions	Yield
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); potassium tert-butylate at 80 - 120℃; for 5h;	68%

1-bromo-2,3-dichlorobenzene (56961-77-4) + bis[4-(2-phenyl-2-propyl)phenyl]amine (10081-67-1) → C66H63ClN2

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate at 130℃; Inert atmosphere;	66.2%

Upstream product

• 608-27-5 2,3-dichloroaniline 
• 113571-16-7 4-Bromo-2,3-dichloroacetanilide 
• 22459-81-0 N-(4-bromo-3-chlorophenyl)acetamide 
• 56978-48-4 4-bromo-2,3-dichloro-phenylamine 

Downstream Products

• 108-37-2 1-bromo-3-chlorobenzene 
• 95-50-1 1,2-dichloro-benzene 
• 1057096-65-7 [(2,3-dichlorophenyl)ethynyl](trimethyl)silane 
• 151169-74-3 2,3-dichlorobenzeneboronic acid 
• 1018948-94-1 tert-butyl 2,3-dichlorobenzoate 
• 1067677-91-1 C₃₂H₃₀Cl₂O₅ 
• 41202-77-1 1-(2,3-dichlorophenyl)piperazine 
• 38444-84-7 2,3,3'-trichlorobiphenyl 
• 89900-87-8 C₁₇H₁₈Cl₂NO 
• 849766-56-9 4-(2,3-dichloro-benzyl)-piperidine 
• 849766-49-0 4-(2,3-dichloro-benzyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 2051-61-8 m-chlorobiphenyl 
• 16605-91-7 2,3-dichlorobiphenyl 

Relevant articles and documents

Isomerization of bromohalogenobenzenes

Bromohalogenobenzenes are isomerized to useful, e.g., pharmaceutical or phytosanitary intermediates, by contacting the same with an alkaline base and a catalyst compound which forms a complex with the cation of said alkaline base.