56962-04-0

Basic information

• Product Name: 3-Bromo-5-chlorophenol
• Synonyms: 3-BroMo-chlorophenol;3-BroMo-5-chlorophenol, 97+%
• CAS NO: 56962-04-0
• Molecular Formula: C₆H₄BrClO
• Molecular Weight: 207.45
• Product Categories: Bromine Compounds;Chlorine Compounds;Phenols
• Mol File: 56962-04-0.mol

Chemical Properties

• Melting Point: 66-70℃
• Boiling Point: 256°C (rough estimate)
• Flash Point: 110.075oC
• Appearance: /Solid
• Density: 1.6027 (rough estimate)
• Vapor Pressure: 0.009mmHg at 25°C
• Refractive Index: 1.5730 (estimate)
• Storage Temp.: Refrigerated.
• PKA: 8.04±0.10(Predicted)
• CAS DataBase Reference: 3-Bromo-5-chlorophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-5-chlorophenol(56962-04-0)
• EPA Substance Registry System: 3-Bromo-5-chlorophenol(56962-04-0)

Safety Data

• Hazardous Substances Data: 56962-04-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Bromo-5-chlorophenol is used as an intermediate in the synthesis of pharmaceuticals, contributing to the development of various medicinal compounds due to its reactive bromine and chlorine atoms that facilitate a range of chemical reactions.
Used in Agrochemical Production:
In the agrochemical industry, 3-Bromo-5-chlorophenol serves as a key intermediate, playing a crucial role in the creation of pesticides and other agricultural chemicals that help protect crops and enhance agricultural productivity.
Used in Dye and Pigment Synthesis:
3-Bromo-5-chlorophenol is utilized as a building block for synthesizing dyes and pigments, taking advantage of its chemical structure to produce a spectrum of colorants for various applications in industries such as textiles, plastics, and printing.
Used in Specialty Chemicals:
3-Bromo-5-chlorophenol is also employed in the synthesis of specialty chemicals, which are often used in niche applications across different industries, capitalizing on the unique properties imparted by the bromine and chlorine atoms on the phenol ring.

InChI:InChI=1/C6H4BrClO/c7-4-1-5(8)3-6(9)2-4/h1-3,9H

Synthetic route

1-bromo-3-chloro-5-methoxybenzene (174913-12-3) → 3-bromo-5-chlorophenol (56962-04-0)

Conditions	Yield
Stage #1: 1-bromo-3-chloro-5-methoxybenzene With lithium iodide In 2,4,6-trimethyl-pyridine at 170℃; for 4h; Stage #2: With hydrogenchloride In 2,4,6-trimethyl-pyridine; water at 20℃;	94%
With hydrogen bromide; acetic acid In water at 120℃; for 40h;
Stage #1: 1-bromo-3-chloro-5-methoxybenzene With boron tribromide In dichloromethane at 20℃; Stage #2: With water In dichloromethane at 20℃;
Stage #1: 1-bromo-3-chloro-5-methoxybenzene With boron tribromide In dichloromethane at 20℃; Stage #2: With water In dichloromethane at 20℃;

1-bromo-3-chlorobenzene (108-37-2) → 3-bromo-5-chlorophenol (56962-04-0)

Conditions	Yield
Stage #1: 1-bromo-3-chlorobenzene With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; for 18h; Inert atmosphere; Stage #2: With Oxone In water; acetone for 0.166667h;	81%
Stage #1: 1-bromo-3-chlorobenzene With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; for 18h; Inert atmosphere; Stage #2: With Oxone In water; acetone for 0.166667h;	81%
Stage #1: 1-bromo-3-chlorobenzene With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; (η5-indenyl)(η4-1,5-cyclooctadiene)iridium(I); 1,2-bis(dimethylphosphanyl)ethane at 150℃; for 3.5h; Inert atmosphere; Stage #2: With Oxone; water In acetone Cooling with ice;	62%
Multi-step reaction with 2 steps 1: 1,2-bis(dimethylphosphino)ethane; (indenyl)Ir(1,5-cyclooctadiene) / 3.5 h / 150 °C 2: aq. oxone / acetone / 0.12 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: 1,2-bis(dimethylphosphanyl)ethane / 150 °C 2: oxone; water / acetone / 0.12 h / 25 °C View Scheme

3-chloro-5-(4-methoxybenzyloxy)bromobenzene (210992-77-1) → 3-bromo-5-chlorophenol (56962-04-0)

Conditions	Yield
With methanesulfonic acid; 1,3-Dimethoxybenzene In toluene at 10℃;	81%

3-chloro-2,4,5,6-tetrabromophenol (87504-69-6) → bromobenzene (108-86-1) + 3-bromo-5-chlorophenol (56962-04-0)

Conditions	Yield
With aluminium trichloride; benzene

3-amino-5-chlorophenol (883195-40-2) → 3-bromo-5-chlorophenol (56962-04-0)

aluminium trichloride (7446-70-0) + 3-chloro-2,4,5,6-tetrabromophenol (87504-69-6) + benzene (71-43-2) → bromobenzene (108-86-1) + 3-bromo-5-chlorophenol (56962-04-0)

2-(3-bromo-5-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 3-bromo-5-chlorophenol (56962-04-0)

Conditions	Yield
With Oxone In acetone at 25℃; for 0.116667h;
With Oxone In water; acetone at 0 - 25℃; for 0.15 - 0.25h;
With Oxone; sodium hydroxide; sodium hydrogencarbonate In water; acetone at 0℃; for 0.25h;
With Oxone; sodium hydroxide In water; acetone at 0℃; for 0.283333 - 0.333333h;
With oxone; water In acetone at 25℃; for 0.116667h;

3-monochlorophenol (108-43-0) → 3-bromo-5-chlorophenol (56962-04-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: iron powder; bromine 2: aluminium chloride; benzene View Scheme

1-bromo-3-chloro-5-fluorobenzene (33863-76-2) → 3-bromo-5-chlorophenol (56962-04-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 40 °C 1.2: 60 °C 2.1: methanesulfonic acid; 1,3-Dimethoxybenzene / toluene / 10 °C View Scheme
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide / 20 °C 2.1: boron tribromide / dichloromethane / 20 °C 2.2: 20 °C View Scheme

4-chloro-3-fluoropicolinonitrile (1155847-43-0) + 3-bromo-5-chlorophenol (56962-04-0) → 3-(3-bromo-5-chlorophenoxy)-4-chloropyridine-2-carbonitrile (1155847-61-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 0.333333h;	100%
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 0.166667h;

C31H28Br4O3 + 3-bromo-5-chlorophenol (56962-04-0) → C55H40Br4Cl4O7

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere; Schlenk technique;	95%

3-bromo-5-chlorophenol (56962-04-0) + 1,3-bis(bromomethyl)-5-benzyloxybenzene → C27H20Br2Cl2O3

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere; Schlenk technique;	93%

3-bromo-5-chlorophenol (56962-04-0) + tert-butyldimethylsilyl chloride (18162-48-6) → (3-bromo-5-chloro-phenoxy)-tert-butyl-dimethyl-silane (1392196-71-2)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 25℃; for 15h;	92%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃;	33 g

2-iodo-propane (75-30-9) + 3-bromo-5-chlorophenol (56962-04-0) → 1-bromo-3-chloro-5-isopropoxybenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;	91%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;	91%

3-bromo-5-chlorophenol (56962-04-0) + benzyl bromide (100-39-0) → 1-benzyloxy-3-bromo-5-chloro-benzene (1187966-48-8)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 2h; Reflux;	90%

(chlorodifluoromethylsulfonyl)benzene (930836-30-9) + 3-bromo-5-chlorophenol (56962-04-0) → 1-bromo-3-chloro-5-(difluoromethoxy)benzene (1004112-67-7)

Conditions	Yield
With potassium hydroxide In acetonitrile at 50℃; for 5h;	89%

3-bromo-5-chlorophenol (56962-04-0) + 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → 1-(tert-butyl) 2-methyl (2S,4S)-4-(3-bromo-5-chlorophenoxy)pyrrolidine-1,2-dicarboxylate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	87%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + 3-bromo-5-chlorophenol (56962-04-0) → 2-(3-bromo-5-chlorophenoxy)-1-chloro-3-nitrobenzene (1034474-41-3)

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 2h; Inert atmosphere;	85.4%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 2h;

3-bromo-5-chlorophenol (56962-04-0) + pivaloyl chloride (3282-30-2) → 3-bromo-5-chlorophenyl pivalate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 25℃;	85%

tetrahydrofuran (109-99-9) + 3-bromo-5-chlorophenol (56962-04-0) → 3-chloro-5-(tetrahydrofuran-2-yl)phenol

Conditions	Yield
With bis(acetylacetonate)nickel(II); 5,5'-dimethyl-2,2'-bipyridine; (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone; sodium carbonate at 20℃; for 72h; Schlenk technique; Inert atmosphere; Irradiation; chemoselective reaction;	84%

2-[2-[2-(benzyloxycarbonylamino)ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate + 3-bromo-5-chlorophenol (56962-04-0) → benzyl (2-(2-(2-(3-bromo-5-chlorophenoxy)ethoxy)ethoxy)ethyl)carbamate

Conditions	Yield
Stage #1: 3-bromo-5-chlorophenol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2-[2-[2-(benzyloxycarbonylamino)ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	84%

trifluorormethanesulfonic acid (1493-13-6) + 3-bromo-5-chlorophenol (56962-04-0) → 3-bromo-5-chlorophenyl trifluoromethanesulfonate

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	82%

iodobenzene (591-50-4) + 3-bromo-5-chlorophenol (56962-04-0) → 1-bromo-3-chloro-5-phenyloxybenzene (1620783-10-9)

Conditions	Yield
With 18-crown-6 ether; copper; potassium carbonate In N,N-dimethyl-formamide at 120℃;	81%

3-bromo-5-chlorophenol (56962-04-0) + p-methoxybenzylmercaptan (6258-60-2) → C14H13ClO2S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; nickel dichloride at 110℃; for 2h;	80%

4,5-dichloro-N-(methoxybenzyl)-2-nitroaniline (1345336-82-4) + 3-bromo-5-chlorophenol (56962-04-0) → 5-(3-bromo-5-chlorophenoxy)-4-chloro-N-(4-methoxybenzyl)-2-nitroaniline (1345336-85-7)

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one Heating; Inert atmosphere;	74%

3-bromo-5-chlorophenol (56962-04-0) + 2-Bromoethyl methyl ether (6482-24-2) → 1-bromo-3-chloro-5-(2-methoxyethoxyl)benzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 18h;	70%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 18h;	70%
With caesium carbonate In acetonitrile at 80℃; for 12h;	17 g
With caesium carbonate In acetonitrile at 80℃; for 12h;	17 g
With caesium carbonate In acetonitrile at 80℃; for 12h;	17 g

2-fluoropyridine (372-48-5) + 3-bromo-5-chlorophenol (56962-04-0) → 2-(3-bromo-5-chlorophenoxy)pyridine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 6h; Ullmann Condensation; Microwave irradiation;	65%

3-bromo-5-chlorophenol (56962-04-0) + 3-tert-butyl-1H-pyrazole-5-amine (82560-12-1) → 3-(5-amino-3-tert-butyl-pyrazol-1-yl)-5-chloro-phenol

Conditions	Yield
With copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine In toluene at 110℃; for 24h; Microwave irradiation; Inert atmosphere;	62%
With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; potassium carbonate In toluene at 110℃; for 24h; Inert atmosphere; Microwave irradiation;	62%

1-bromo-3-chloro-5-fluorobenzene (33863-76-2) + 3-bromo-5-chlorophenol (56962-04-0) → C12H6Br2Cl2O

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 180℃; for 16h;	60%

3-bromo-5-chlorophenol (56962-04-0) + 1-cyclohexyl-2,4,6-triphenylpyridin-1-ium tetrafluoroborate salt → 3-chloro-5-cyclohexylphenol

Conditions	Yield
With nickel(II) bromide dimethoxyethane; manganese; 4,4'-Dimethoxy-2,2'-bipyridin In 1-methyl-pyrrolidin-2-one at 20℃; for 20h; Inert atmosphere; chemoselective reaction;	51%

(6-(4-(dimethylamino)piperidin-1-yl)pyridin-3-yl)boronic acid + 3-bromo-5-chlorophenol (56962-04-0) → 3-chloro-5-{6-[4-(dimethylamino)piperidin-1-yl]pyridin-3-yl}phenol

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 90℃; Inert atmosphere; Schlenk technique;	50%

1-methyl-piperazine (109-01-3) + 3-bromo-5-chlorophenol (56962-04-0) → 3-chloro-5-(4-methylpiperazin-1-yl)phenol

Conditions	Yield
With palladium diacetate; lithium hexamethyldisilazane; 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane In toluene at 80℃; Inert atmosphere;	45%

(1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5-(methoxycarbonyl)-3-methyl-1H-pyrazol-4-yl)boronic acid + 3-bromo-5-chlorophenol (56962-04-0) → C24H20Cl3N3O3S2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 85℃; for 16h; Inert atmosphere;	41%

formaldehyd (50-00-0) + 3-bromo-5-chlorophenol (56962-04-0) → 3-bromo-5-chloro-4-(hydroxymethyl)phenol

Conditions	Yield
With water; sodium hydroxide at 45℃;	31%

3-bromo-5-chlorophenol (56962-04-0) + bis(pinacol)diborane (73183-34-3) → 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (960388-56-1)

Conditions	Yield
With water; potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,2-dimethoxyethane at 150℃; for 0.25h;	28%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 150℃; for 0.25h; Irradiation in a microwave;	28%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 150℃; for 0.25h; Microwave irradiation;	28%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane at 150℃; for 0.25h; Microwave irradiation;	28%

3-bromo-5-chlorophenol (56962-04-0) + phenylboronic acid (98-80-6) → 1-bromo-3-chloro-5-phenyloxybenzene (1620783-10-9)

Conditions	Yield
With copper diacetate; triethylamine In dichloromethane at 20℃; for 3h; Molecular sieve;	20%

Upstream product

• 87504-69-6 3-chloro-2,4,5,6-tetrabromophenol 
• 883195-40-2 3-amino-5-chlorophenol 
• 7446-70-0 aluminium trichloride 
• 71-43-2 benzene 
• 488850-91-5 2-(3-bromo-5-chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 174913-12-3 1-bromo-3-chloro-5-methoxybenzene 
• 33863-76-2 1-bromo-3-chloro-5-fluorobenzene 
• 210992-77-1 3-chloro-5-(4-methoxybenzyloxy)bromobenzene 
• 108-43-0 3-monochlorophenol 
• 108-37-2 1-bromo-3-chlorobenzene 

Downstream Products

• 855839-00-8 3,4-dibromo-5-chloro-phenol 
• 846040-53-7 3-bromo-2,4,5,6-tetrachloro-phenol 
• 855836-56-5 3-bromo-5-chloro-2,4,6-triiodo-phenol 
• 1004112-67-7 1-bromo-3-chloro-5-(difluoromethoxy)benzene 
• 874974-96-6 [3-(3-bromo-5-chloro-phenoxy)-2-fluoro-4-nitro-phenyl]-acetic acid ethyl ester 
• 1620783-11-0 N³-(3-chloro-5-phenoxyphenyl)-1,N⁵,N⁵-tris-(4-methoxybenzyl)-1H-[1,2,4]triazole-3,5-diamine 
• 1620782-75-3 N³-(3-chloro-5-phenoxphenyl)-1H-[1,2,4]triazole-3,5-diamine 
• 1620783-10-9 1-bromo-3-chloro-5-phenyloxybenzene 
• 1034474-46-8 tert-butyl {2-[[(3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridin-1-yl)carbonyl](methyl)amino]ethyl}carbamate 
• 1034474-45-7 tert-butyl {2-[[(3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridin-1-yl)carbonyl](methyl)amino]ethyl}methylcarbamate 
• 1034474-24-2 2-[[(3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridin-1-yl)carbonyl](methyl)amino]ethanaminium chloride 
• 1034474-22-0 2-[[(3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridin-1-yl)carbonyl](methyl)amino]-N-methylethanaminium chloride 

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