183802-98-4

Basic information

• Product Name: 5-Bromo-2-chlorophenol
• Synonyms: 2-ch1oro-5-bromophenol;5-Bromo-2-chlorophenol, 98+%;5-Bromo-2-chlorophenol ,97%;5-BROMO-2-CHLOROPHENOL;2-chloro-5-bromophenol
• CAS NO: 183802-98-4
• Molecular Formula: C₆H₄BrClO
• Molecular Weight: 207.45
• Product Categories: Phenol&Thiophenol&Mercaptan;Bromine Compounds;Chlorine Compounds;Phenols
• Mol File: 183802-98-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 46-47
• Boiling Point: 234°C(lit.)
• Flash Point: 95.9 ºC
• Appearance: Light yellow to White crystals
• Density: 1.788 g/cm³
• Vapor Pressure: 0.0337mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 7.53±0.10(Predicted)
• CAS DataBase Reference: 5-Bromo-2-chlorophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-chlorophenol(183802-98-4)
• EPA Substance Registry System: 5-Bromo-2-chlorophenol(183802-98-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-36/37
• Hazardous Substances Data: 183802-98-4(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to White crystals

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

Synthetic route

5-Bromo-2-chloroanisole (16817-43-9) → 5-bromo-2-chlorophenol (183802-98-4)

Conditions	Yield
Stage #1: 5-Bromo-2-chloroanisole With boron tribromide In dichloromethane at 0 - 20℃; for 20.6667h; Stage #2: With water In dichloromethane at 0℃; for 0.5h;	98%
Stage #1: 5-Bromo-2-chloroanisole With boron tribromide In dichloromethane at 0 - 20℃; for 14h; Stage #2: With potassium carbonate In water at 0℃; Stage #3: With hydrogenchloride In water	96%
Stage #1: 5-Bromo-2-chloroanisole With boron tribromide In dichloromethane at 0 - 20℃; for 14h; Stage #2: With water; potassium carbonate In dichloromethane Stage #3: With hydrogenchloride In water	96%
Stage #1: 5-Bromo-2-chloroanisole With boron tribromide In dichloromethane at 0 - 20℃; for 4h; Stage #2: With sodium hydroxide; water In dichloromethane Stage #3: With hydrogenchloride In water	95%
With boron tribromide In dichloromethane at 0 - 20℃; for 7h;

3-Bromophenol (591-20-8) → 3-bromo-4-chlorophenol (13659-24-0) + 5-bromo-2-chlorophenol (183802-98-4) + 3 -bromo-2-chlorophenol (863870-87-5)

Conditions	Yield
With N-chloro-succinimide; (R)-[1,1′-binaphthalene]-2,2′-diylbis-(diphenylphosphine sulfide) In chloroform-d1 at 20℃; for 2h; regioselective reaction;	A 72% B n/a C n/a
With N-chloro-succinimide; C24H20F12N4OS In chloroform-d1 at 20℃; for 3h; regioselective reaction;	A n/a B 48% C 14%
With 1,3-dichloro-5,5-dimethylhydantoin; diisopropylamine hydrochloride In toluene at 0℃; for 4h; Darkness; Overall yield = 57 %; regioselective reaction;

3-Bromophenol (591-20-8) → 3-bromo-4-chlorophenol (13659-24-0) + 5-bromo-2-chlorophenol (183802-98-4)

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 20℃; for 12h; regioselective reaction;	A n/a B 60%

4-bromo-1,2-dichlorobenzene (18282-59-2) + sodium methylate (124-41-4) → 5-bromo-2-chlorophenol (183802-98-4)

Conditions	Yield
With methanol at 180℃;

5-bromo-2-chloroaniline (60811-17-8) → 5-bromo-2-chlorophenol (183802-98-4)

Conditions	Yield
With sulfuric acid Diazotization.Erhitzen der Diazoniumsalz-Loesung;

2,3,4-tribromo-6-chloro-phenol (876487-15-9) + benzene (71-43-2) → bromobenzene (108-86-1) + 5-bromo-2-chlorophenol (183802-98-4)

Conditions	Yield
With aluminium trichloride

aluminium trichloride (7446-70-0) + 2,3,4-tribromo-6-chloro-phenol (876487-15-9) + benzene (71-43-2) → bromobenzene (108-86-1) + 5-bromo-2-chlorophenol (183802-98-4)

m,p-dichloroaniline (95-76-1) → 5-bromo-2-chlorophenol (183802-98-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuBr und HBr 2: methanol / 180 °C View Scheme

5-Bromo-2-chloroanisole (16817-43-9) → 5-bromo-2-chlorophenol (183802-98-4) + phenol (108-95-2)

Conditions	Yield
With boron tribromide In dichloromethane

5-bromo-2-chlorophenol (183802-98-4) + 2-chloro-5-trifluoromethylpyridine (52334-81-3) → 2-(5-bromo-2-chlorophenoxy)-5-(trifluoromethyl)pyridine (1020330-54-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 110℃; for 12h;	100%

5-bromo-2-chlorophenol (183802-98-4) + benzyl bromide (100-39-0) → 2-benzyloxy-4-bromo-1-chloro-benzene (903579-12-4)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 16h;	100%

3-bromopropanol methyl ether (36865-41-5) + 5-bromo-2-chlorophenol (183802-98-4) → 4-bromo-1-chloro-2-(3-methoxypropoxy)benzene (897954-59-5)

Conditions	Yield
With potassium carbonate In acetone at 50℃; for 15h; Solvent;	99.44%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h;	91%
With potassium carbonate at 20℃; for 16h;	89.1%

5-bromo-2-chlorophenol (183802-98-4) + ethyl iodide (75-03-6) → 1-bromo-4-chloro-3-ethoxybenzene (900174-61-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 55℃; for 3h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 3h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 3h;	94%
With potassium carbonate In acetone at 55℃; for 18h; Sealed tube;

zinc cyanide (748101-41-9) + 5-bromo-2-chlorophenol (183802-98-4) → 4-chloro-3-hydroxybenzonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide	94%

2-(tert-butoxycarbonylamino)ethyl bromide (39684-80-5) + 5-bromo-2-chlorophenol (183802-98-4) → tert-butyl (2-(5-bromo-2-chlorophenoxy)ethyl)carbamate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 6h;	91%

cyclopropyl bromide (4333-56-6) + 5-bromo-2-chlorophenol (183802-98-4) → 4-bromo-1-chloro-2-(cyclopropoxy)benzene (1201196-54-4)

Conditions	Yield
With caesium carbonate In N,N-dimethyl acetamide at 150℃; for 47h;	87%
With caesium carbonate In dimethyl sulfoxide at 170℃; for 48h; High pressure;

oxetan-3-ol (7748-36-9) + 5-bromo-2-chlorophenol (183802-98-4) → 3-(5-bromo-2-chlorophenoxy)oxetane

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 18h;	87%

(3-bromophenyl)boronic acid (89598-96-9) + 5-bromo-2-chlorophenol (183802-98-4) → C12H8BrClO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 5h; Inert atmosphere;	85.42%

5-bromo-2-chlorophenol (183802-98-4) → 5-bromo-2-chloro-4-nitrophenol (48125-11-7)

Conditions	Yield
With nitric acid In chloroform at 0 - 5℃; for 1.16667h;	82%

5-bromo-2-chlorophenol (183802-98-4) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-(tert-butyldimethylsilyl)-2-chlorophenol

Conditions	Yield
Stage #1: 5-bromo-2-chlorophenol; tert-butyldimethylsilyl chloride With triethylamine In dichloromethane at 0℃; for 4h; Stage #2: tert-butyldimethylsilyl chloride With n-butyllithium In tetrahydrofuran at -78 - 60℃; Inert atmosphere; Stage #3: With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 0.5h;	82%

5-bromo-2-chlorophenol (183802-98-4) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → 4'-chloro-3'-hydroxy[1,1'-biphenyl]-4-carboxylate (1198422-80-8)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In ethanol; water; toluene for 0.5h; Suzuki coupling; Reflux; Inert atmosphere;	81%

2-Chloro-N-cyclohexylacetamide (23605-23-4) + 5-bromo-2-chlorophenol (183802-98-4) → (5-bromo-2-chlorophenoxy)-N-cyclohexylacetamide

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 4.5h;	80%

(6S)-2-nitro-6-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (1188329-66-9) + 5-bromo-2-chlorophenol (183802-98-4) → 4-chloro-40-({[(6S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b]-[1,3]oxazin-6-yl]oxy}methyl)[1,10-biphenyl]-3-ol (1198422-57-9)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In ethanol; water; toluene for 1h; Suzuki coupling; Inert atmosphere; Reflux;	76%

tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydropyrrole-1-carboxylate (212127-83-8) + 5-bromo-2-chlorophenol (183802-98-4) → 1-tert-butoxycarbonyl-3-(3-hydroxy-4-chlorophenyl)-2,5-dihydropyrrole

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In N,N-dimethyl-formamide at 100℃; Inert atmosphere;	76%

5-bromo-2-chlorophenol (183802-98-4) + cis-4-(tert-butyl-diphenylsilyloxy)-cyclohexanol (130745-64-1) → 1-bromo-3-[cis-4-(tert-butyl-diphenylsilyloxy)-cyclohexyloxy]-4-chloro-benzene (874650-36-9)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 55℃; for 48h;	72%

5-bromo-2-chlorophenol (183802-98-4) + trans-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]cyclohexanol (130745-65-2) → 1-bromo-3-[cis-4-(tert-butyl-diphenylsilyloxy)-cyclohexyloxy]-4-chloro-benzene (874650-36-9)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 55℃; for 48h;	72%

5-bromo-2-chlorophenol (183802-98-4) + 3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester (141699-57-2) → tert-butyl 3-(5-bromo-2-chlorophenoxy)pyrrolidine-1-carboxylate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 16h;	72%

5-bromo-2-chlorophenol (183802-98-4) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-5-bromo-2-chlorophenyl N,N-dimethylcarbamothioate (740806-61-5)

Conditions	Yield
Stage #1: 5-bromo-2-chlorophenol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #2: N,N-Dimethylthiocarbamoyl chloride In tetrahydrofuran; mineral oil at 20℃;	70%
With potassium carbonate In tetrahydrofuran; water

5-bromo-2-chlorophenol (183802-98-4) + 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) → 5-bromo-2-chlorophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (1259428-86-8)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In toluene at 20℃; for 5h; Inert atmosphere;	67%

ethyl 2-chloro-2,2-difluoroacetate (383-62-0) + 5-bromo-2-chlorophenol (183802-98-4) → 4-Bromo-1-chloro-2-(difluoromethoxy)benzene (1000575-20-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	67%

diethyl (bromodifluoromethyl)phosphonate (65094-22-6) + 5-bromo-2-chlorophenol (183802-98-4) → 4-bromo-1-chloro-2-(difluoromethoxy-d1)benzene

Conditions	Yield
Stage #1: 5-bromo-2-chlorophenol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: With water-d2 In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Inert atmosphere; Stage #3: diethyl (bromodifluoromethyl)phosphonate In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;	65%

5-bromo-2-chlorophenol (183802-98-4) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 4-bromo-1-chloro-2-(2,2-diethoxyethoxy)benzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 18h;	64%
With potassium carbonate In N,N-dimethyl-formamide at 135℃; for 7h;
With potassium carbonate In N,N-dimethyl-formamide at 135℃; for 7h;

5-bromo-2-chlorophenol (183802-98-4) + 5-methylene-1,3,2-dioxathiane 2-oxide (548482-49-1) → 2-((5-bromo-2-chlorophenoxy)methyl)prop-2-en-1-ol

Conditions	Yield
Stage #1: 5-bromo-2-chlorophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: 5-methylene-1,3,2-dioxathiane 2-oxide In N,N-dimethyl-formamide; mineral oil at 55℃; for 4h;	60%

triisopropylsilyl chloride (13154-24-0) + 5-bromo-2-chlorophenol (183802-98-4) → 1-bromo-4-chloro-3-(tri-isopropyl-silyloxy)-benzene (874650-34-7)

Conditions	Yield
With triethylamine; dmap In dichloromethane at 0 - 20℃; for 18h;	59%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 18h;

5-bromo-2-chlorophenol (183802-98-4) + 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate (141699-59-4) → tert-butyl 4-(5-bromo-2-chlorophenoxy)piperidine-1-carboxylate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 16h;	57%

5-bromo-2-chlorophenol (183802-98-4) + 3-hydroxycyclopentyl 4-methylbenzenesulfonate (874650-39-2) → 1-bromo-3-(cis-3-hydroxy-cyclopent-1-yloxy)-4-chloro-benzene

Conditions	Yield
Stage #1: 5-bromo-2-chlorophenol With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 3-hydroxycyclopentyl 4-methylbenzenesulfonate In DMF (N,N-dimethyl-formamide) at 65℃; for 16h;	50%

Upstream product

• 18282-59-2 4-bromo-1,2-dichlorobenzene 
• 124-41-4 sodium methylate 
• 591-20-8 3-Bromophenol 
• 16817-43-9 5-Bromo-2-chloroanisole 
• 95-76-1 m,p-dichloroaniline 
• 7446-70-0 aluminium trichloride 
• 876487-15-9 2,3,4-tribromo-6-chloro-phenol 
• 71-43-2 benzene 
• 60811-17-8 5-bromo-2-chloroaniline 

Downstream Products

• 85117-86-8 3-bromo-2,4,6-trichloro-phenol 
• 876487-15-9 2,3,4-tribromo-6-chloro-phenol 
• 740806-96-6 1-[4-Chloro-3-(2-ethoxy-ethoxy)-phenyl]-piperazine 
• 915201-06-8 (4-chloro-3-hydroxyphenyl)boronic acid 

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