3964-56-5

Basic information

• Product Name: 4-Bromo-2-chlorophenol
• Synonyms: 4-BROMO-2-CHLOROPHENOL;AKOS BBB/367;2-CHLORO-4-BROMO PHENOL;4-Bromo-2-Chloro Phenol 2-Chloro-4-Bromo Phenol;4-Bromo-2-chlorophenol,98%;4-Bromo-2-chlorophenol,99%;4-BroMo-2-chlorophenol, 99% 25GR;4-BroMo-2-chlorophenol, 99% 5GR
• CAS NO: 3964-56-5
• Molecular Formula: C₆H₄BrClO
• Molecular Weight: 207.45
• EINECS: 223-572-5
• Product Categories: Aromatic Phenols;Phenol&Thiophenol&Mercaptan;Bromine Compounds;Chlorine Compounds;Phenols;Organic Building Blocks;Oxygen Compounds;API Intermediate;Pyrazines
• Mol File: 3964-56-5.mol
• Article Data: 46

Chemical Properties

• Melting Point: 47-49 °C(lit.)
• Boiling Point: 232-235 °C(lit.)
• Flash Point: >230 °F
• Appearance: White to off-white/Low Melting Mass or Crystalline Needles, Powder and Chunks
• Density: 1.6170
• Vapor Pressure: 0.037mmHg at 25°C
• Refractive Index: 1.5859
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.92±0.18(Predicted)
• Water Solubility: Practically insoluble in water
• BRN: 2042867
• CAS DataBase Reference: 4-Bromo-2-chlorophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-chlorophenol(3964-56-5)
• EPA Substance Registry System: 4-Bromo-2-chlorophenol(3964-56-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3964-56-5(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white low melting mass or crystalline

Uses

4-Bromo-2-chlorophenol was used as reagent during the synthesis of 7-arylbenzo[b][1,4]oxazin derivatives.

Definition

ChEBI: A halophenol that is phenol in which the hydrogens at positions 2 and 4 have been replaced by chlorine and bromine, respectively.

General Description

4-Bromo-2-chlorophenol is biologically inactive metabolite of profenofos, an organophosphorus pesticide. It undergoes enzyme-catalyzed copolymerization with phenols catalyzed by extracellular laccase of the fungus Rhizoctonia praticola.

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

Synthetic route

2-monochlorophenol (95-57-8) → 4-bromo-2-chlorophenol (3964-56-5)

Conditions	Yield
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 7h; Heating;	100%
With sulfuric acid; C20H22Br2N2O5V; dihydrogen peroxide In methanol; water at 20℃; for 1.33333h; Catalytic behavior;	100%
With N-benzyl-N,N-dimethyl anilinium peroxodisulfate; potassium bromide In acetonitrile for 1.5h; Reflux; regioselective reaction;	97%

4-bromo-phenol (106-41-2) → 4-bromo-2-chlorophenol (3964-56-5)

Conditions	Yield
With 1,3-dichloro-5,5-dimethylhydantoin; diisopropylamine hydrochloride In toluene at 0℃; for 4h; Darkness; regioselective reaction;	91%
With potassium hydrogensulfate; potassium chloride; isoquinolinium dichromate In water at 20℃; Catalytic behavior; Reagent/catalyst; Temperature; Sonication; Green chemistry; regioselective reaction;	69%
With N-chloro-3-methyl-2,6-diphenylpiperidin-4-one; hydrogen cation In ethanol; water at 30℃; Product distribution; Thermodynamic data; ΔH(excit.), ΔS(excit.);

(4-bromo-2-chloro-phenoxy)-tert-butyl-dimethyl-silane → 4-bromo-2-chlorophenol (3964-56-5)

Conditions	Yield
With tin(ll) chloride In ethanol at 20℃; for 5h;	87%

2-monochlorophenol (95-57-8) + di-isopropyl azodicarboxylate (2446-83-5) → bis(1-methylethyl) 1,2-hydrazinedicarboxylate (19740-72-8) + 4-bromo-2-chlorophenol (3964-56-5)

Conditions	Yield
With ZrBr4 In dichloromethane at 20℃; for 8h;	A n/a B 76%

2-monochlorophenol (95-57-8) → 4-bromo-2-chlorophenol (3964-56-5) + 2-bromo-6-chlorophenol (2040-88-2) + 2,4-dibromo-6-chlorophenol (4526-56-1)

Conditions	Yield
With N-Bromosuccinimide; thiourea In acetonitrile at 20℃; for 2h; regioselective reaction;	A 75% B 6 %Chromat. C 6 %Chromat.
With 4-morpholineethanesulfonic acid; VBrPO(AnI) bromoperoxidase; dihydrogen peroxide; sodium bromide In water; tert-butyl alcohol at 23℃; pH=6.2; Overall yield = 39 %;	A n/a B n/a C 26%
With tetrafluoroboric acid diethyl ether; N-Bromosuccinimide In acetonitrile for 7.5h; Ambient temperature; Yield given. Yields of byproduct given;

2,4-dibromo-6-chlorophenol (4526-56-1) → 4-bromo-2-chlorophenol (3964-56-5)

Conditions	Yield
With acetic acid; zinc

4-bromo-2-chloro-1-methoxybenzene (50638-47-6) → 4-bromo-2-chlorophenol (3964-56-5)

Conditions	Yield
With hydrogen bromide; acetic acid

6-bromo-2-chloro-3-hydroxy-benzaldehyde (704892-51-3) → 4-bromo-2-chlorophenol (3964-56-5)

Conditions	Yield
With potassium hydroxide

2-monochlorophenol (95-57-8) → 4-bromo-2-chlorophenol (3964-56-5) + 2-bromo-6-chlorophenol (2040-88-2)

Conditions	Yield
With Amberlyst-A26 tribromide In dichloromethane for 24h; Ambient temperature; Title compound not separated from byproducts;	A 76 % Chromat. B 20 % Chromat.
With oxone; ammonium bromide In acetonitrile at 20℃; for 5h;
Stage #1: 2-monochlorophenol With β‐cyclodextrin for 12h; Stage #2: With bromine In methanol; tetrachloromethane at 20℃; for 2h; Further stages.;
With sulfuric acid; dihydrogen peroxide; cetyltrimethylammonim bromide; sodium dodecyl-sulfate; sodium bromide for 2h; Micellar solution;

2,4-dibromo-6-chlorophenol (4526-56-1) + acetic acid (64-19-7) + zinc dust → 4-bromo-2-chlorophenol (3964-56-5)

6-bromo-2-chloro-3-hydroxy-benzaldehyde (704892-51-3) + aqueous KOH-solution → formic acid (64-18-6) + 4-bromo-2-chlorophenol (3964-56-5)

(S)-2-{(4-Bromo-2-chloro-phenoxy)-[(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethoxy]-phosphorylamino}-propionic acid methyl ester → 4-bromo-2-chlorophenol (3964-56-5) + alaninyl-d4T-monophosphate (180076-92-0)

Conditions	Yield
With Subtilisin Carlsberg serine protease In methanol; water at 20℃; Kinetics; Further Variations:; Reagents;

2-monochlorophenol (95-57-8) → 4-bromo-2-chlorophenol (3964-56-5) + 2,4-dibromo-6-chlorophenol (4526-56-1)

Conditions	Yield
Stage #1: 2-monochlorophenol With β‐cyclodextrin for 12h; Stage #2: With bromine In methanol; tetrachloromethane at 20℃; for 6h; Further stages.;
With N-Bromosuccinimide In acetonitrile at 20℃; for 2h; regioselective reaction;
With vanadate(V)-dependent bromoperoxidase I from Ascophyllum nodosum; dihydrogen peroxide; sodium bromide In water; tert-butyl alcohol at 23℃; for 72h; pH=6.2; Enzymatic reaction; Overall yield = 130 mg;

2-bromo-5-hydroxybenzaldehyde (2973-80-0) → 4-bromo-2-chlorophenol (3964-56-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: carbon dioxide; acetic acid; chlorine / 50 °C 2: aqueous KOH View Scheme

phenol (108-95-2) → 4-bromo-2-chlorophenol (3964-56-5) + 2-bromo-6-chlorophenol (2040-88-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; sulfuric acid; dihydrogen peroxide; cetyltrimethylammonim bromide; sodium dodecyl-sulfate / water / 4 h / Micellar solution 2: sulfuric acid; dihydrogen peroxide; cetyltrimethylammonim bromide; sodium dodecyl-sulfate; sodium bromide / 2 h / Micellar solution View Scheme

Profenofos (41198-08-7) → 4-bromo-2-chlorophenol (3964-56-5)

Conditions	Yield
With C25H32Cl3N2OV; water In chloroform-d1 for 3h; Reagent/catalyst; Time; UV-irradiation;

1-bromo-3-chloro-4-fluorobenzene (60811-21-4) → 4-bromo-2-chlorophenol (3964-56-5)

Conditions	Yield
With syn-benzaldehyde oxime; N1,N2-bis(thiophen-2-ylmethyl)oxalamide; caesium carbonate; copper(l) chloride In dimethyl sulfoxide at 80℃; for 20h; Glovebox; Schlenk technique; Sealed tube; Inert atmosphere;

triisopropylsilyl chloride (13154-24-0) + 4-bromo-2-chlorophenol (3964-56-5) → 1-bromo-3-chloro-4-triisopropylsilyloxybenzene

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	100%
With 1H-imidazole In dichloromethane at 20℃; for 2h;	99.8%
With 1H-imidazole In dichloromethane at 20℃; for 2h;	99.8%

2-chloroethyl tosylate (80-41-1) + 4-bromo-2-chlorophenol (3964-56-5) → C8H7BrCl2O (869569-66-4)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 60℃; for 3h;	100%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;

4-bromo-2-chlorophenol (3964-56-5) + ethyl bromoacetate (105-36-2) → ethyl 2-(4-bromo-2-chlorophenoxy)acetate (588679-10-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 100℃; for 4h;	100%
With potassium carbonate In N,N-dimethyl-formamide at 70℃;	84.1%
With potassium carbonate In N,N-dimethyl-formamide at 70℃;	84.1%
With potassium carbonate In N,N-dimethyl-formamide at 70℃;

4-bromo-2-chlorophenol (3964-56-5) + methyl iodide (74-88-4) → 4-bromo-2-chloro-1-methoxybenzene (50638-47-6)

Conditions	Yield
Stage #1: 4-bromo-2-chlorophenol With caesium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: methyl iodide In N,N-dimethyl-formamide at 50℃;	100%
In tetrahydrofuran	98%
Stage #1: 4-bromo-2-chlorophenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 70℃; for 18.1667h; Inert atmosphere;	97%

2-chloroethyl-p-toluenesulfonate (22381-53-9) + 4-bromo-2-chlorophenol (3964-56-5) → C8H7BrCl2O (869569-66-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;	100%

4-bromo-2-chlorophenol (3964-56-5) + chloroacetic acid ethyl ester (105-39-5) → ethyl 2-(4-bromo-2-chlorophenoxy)acetate (588679-10-1)

Conditions	Yield
Stage #1: 4-bromo-2-chlorophenol; chloroacetic acid ethyl ester With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere; Stage #2: chloroacetic acid ethyl ester In N,N-dimethyl-formamide at 20℃;	100%

4-bromo-2-chlorophenol (3964-56-5) + 4-Fluoronitrobenzene (350-46-9) → 4-bromo-2-chloro-1-(4-nitrophenoxy)benzene (38100-79-7)

Conditions	Yield
Stage #1: 4-bromo-2-chlorophenol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: 4-Fluoronitrobenzene In N,N-dimethyl-formamide at 100℃; for 3.5h;	100%

4-bromo-2-chlorophenol (3964-56-5) + cyanomethyl bromide (590-17-0) → 2-(4-bromo-2-chlorophenoxy)acetonitrile

Conditions	Yield
With potassium carbonate In acetone at 20℃;	100%

bromoacetic acid tert-butyl ester (5292-43-3) + 4-bromo-2-chlorophenol (3964-56-5) → tert-butyl 2-(4-bromo-2-chlorophenoxy)acetate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 18h;	99.8%

4-bromo-2-chlorophenol (3964-56-5) + benzyl bromide (100-39-0) → 1-(benzyloxy)-4-bromo-2-chlorobenzene (56872-27-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	99%
With potassium carbonate In acetone for 5h; Heating;	93%
With potassium carbonate In acetone for 2h; Benzylation; Heating;	90%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;	83%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;

4-bromo-2-chlorophenol (3964-56-5) + phenylboronic acid (98-80-6) → 2-chloro-4-phenylphenol (92-04-6)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 95℃; Suzuki reaction;	99%

4-bromo-2-chlorophenol (3964-56-5) + tert-butyldimethylsilyl chloride (18162-48-6) → (4-bromo-2-chloro-phenoxy)-tert-butyl-dimethyl-silane

Conditions	Yield
With 1H-imidazole In MC at 20℃; for 24h; Inert atmosphere;	99%
With 1H-imidazole In dichloromethane at 20℃; for 4h;	91%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h;	86%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 3h;	708 mg

4-bromo-2-chlorophenol (3964-56-5) + chloromethyl methyl ether (107-30-2) → 4-bromo-2-chloro-1-(methoxymethoxy)benzene (1301146-84-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 17h;	99%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;

4-bromo-2-chlorophenol (3964-56-5) + diethyl phosphorochloridothioate (2524-04-1) → O,O-diethyl O-(2-chloro-4-bromophenyl)thiophosphate

Conditions	Yield
Stage #1: 4-bromo-2-chlorophenol With potassium hydroxide at 80℃; for 2h; Large scale; Stage #2: diethyl phosphorochloridothioate With trimethylamine In water at 50℃; for 6h; Temperature; Large scale;	98.5%
With triethylamine In chlorobenzene at 10 - 20℃; for 12h;

4-bromo-2-chlorophenol (3964-56-5) + dimethyl sulfate (77-78-1) → 4-bromo-2-chloro-1-methoxybenzene (50638-47-6)

Conditions	Yield
With potassium carbonate In acetone for 5h; Heating;	98%
With potassium carbonate In acetone for 2h; Heating;	96%

Cyclopentyl bromide (137-43-9) + 4-bromo-2-chlorophenol (3964-56-5) → 4-bromo-2-chloro-1-(cyclopentyloxy)benzene (1310949-91-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 96h;	98%
With caesium carbonate In N,N-dimethyl acetamide at 150℃; for 16h;
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 145 - 155℃; for 24h;

4-bromo-2-chlorophenol (3964-56-5) + propyl bromide (106-94-5) → 4-bromo-2-chloro-1-propoxybenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 22h;	98%

1-bromo-hexane (111-25-1) + 4-bromo-2-chlorophenol (3964-56-5) → 4-bromo-2-chloro-1-(hexyloxy)benzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 18h;	98%

7-bromo-hept-1-ene (4117-09-3) + 4-bromo-2-chlorophenol (3964-56-5) → 4-bromo-2-chloro-1-(hept-6-en-1-yloxy)benzene

Conditions	Yield
With potassium carbonate In acetonitrile for 12h; Reflux;	98%

hexamethylenetetramine (100-97-0) + 4-bromo-2-chlorophenol (3964-56-5) → 5-bromo-3-chloro-2-hydroxybenzaldehyde (19652-33-6)

Conditions	Yield
With trifluoroacetic acid at 0 - 90℃; for 16.5h; Duff Aldehyde Synthesis;	96%
With trifluoroacetic acid at 0 - 90℃; for 17h;	74%
Stage #1: hexamethylenetetramine; 4-bromo-2-chlorophenol With trifluoroacetic acid at 90℃; for 20h; Duff reaction; Stage #2: With sulfuric acid at 20℃; for 2h;	36%

4-bromo-2-chlorophenol (3964-56-5) + 1-chloro-3-hydroxypropane (627-30-5) → 3-(4-bromo-2-chlorophenoxy)propan-1-ol

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Inert atmosphere; Schlenk technique;	96%

4-bromo-2-chlorophenol (3964-56-5) + 2-chloromethylpyridine hydrochloride (6959-47-3) → 2-((4-bromo-2-chlorophenoxy)methyl)pyridine

Conditions	Yield
With sodium hydroxide In acetonitrile at 50℃; for 4h;	95.9%

4-bromo-2-chlorophenol (3964-56-5) + 2-hydroxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane (1246443-46-8) → 2-((4-bromo-2-chlorophenoxy)methyl)-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane (1246443-47-9)

Conditions	Yield
toluene-4-sulfonic acid In toluene at 28℃; for 13h; Reflux;	95%
toluene-4-sulfonic acid In toluene for 13h; Reflux;	95%

Tetrahydro-pyran-4-ol (2081-44-9) + 4-bromo-2-chlorophenol (3964-56-5) → 4-(4-bromo-2-chlorophenoxy)tetrahydropyrane (1056465-06-5)

Conditions	Yield
With di-tert-butyl-diazodicarboxylate In dichloromethane at 0 - 20℃; for 2h;	95%
With di-tert-butyl-diazodicarboxylate In dichloromethane at 0 - 20℃; for 2h; Mitsunobu reaction;	95%
With di-tert-butyl-diazodicarboxylate In dichloromethane at 0 - 20℃; for 2.08333h; Mitsunobu reaction;	95%

4-bromo-2-chlorophenol (3964-56-5) + 4-i-propylbenzyl bromide (73789-86-3) → C16H16BrClO

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	95%

4-bromo-2-chlorophenol (3964-56-5) + o-fluorophenylboronic acid (1993-03-9) → 3-chloro-2'-fluoro-[1,1'-biphenyl]-4-ol

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 90℃; for 12h; Inert atmosphere;	95%

4-bromo-2-chlorophenol (3964-56-5) → 5-bromo-3-chloro-2-hydroxybenzene-1-sulfonyl chloride

Conditions	Yield
With chlorosulfonic acid at 20℃; for 2h; Time; Temperature;	94%
With chlorosulfonic acid at 20℃; for 2h;	93.57%
With chlorosulfonic acid at 0℃; for 24h;	72%
With chlorosulfonic acid at -10℃;	72%

4-bromo-2-chlorophenol (3964-56-5) + acetic anhydride (108-24-7) → 4-bromo-2-chlorophenyl acetate (102932-05-8)

Conditions	Yield
With zinc perchlorate In diethyl ether at 23℃; for 16h;	92%
With pyridine In dichloromethane at 20℃; for 12h; Cooling with ice;	59.9 g

Upstream product

• 106-41-2 4-bromo-phenol 
• 95-57-8 2-monochlorophenol 
• 2446-83-5 di-isopropyl azodicarboxylate 
• 60811-21-4 1-bromo-3-chloro-4-fluorobenzene 
• 108-95-2 phenol 
• 2973-80-0 2-bromo-5-hydroxybenzaldehyde 
• 704892-51-3 6-bromo-2-chloro-3-hydroxy-benzaldehyde 
• 50638-47-6 4-bromo-2-chloro-1-methoxybenzene 
• 4526-56-1 2,4-dibromo-6-chlorophenol 
• 41198-08-7 Profenofos 
• 64-19-7 acetic acid 

Downstream Products

• 32861-94-2 C₁₄H₁₁BrClNO₄ 
• 32861-96-4 C₁₅H₁₃BrClNO₄ 
• 28253-83-0 Thiophosphoric acid O-(4-bromo-2-chloro-phenyl) ester O'-(2-methoxy-ethyl) ester O''-methyl ester 
• 28253-84-1 Thiophosphoric acid O-(4-bromo-2-chloro-phenyl) ester O'-ethyl ester O''-(2-methoxy-ethyl) ester 
• 86808-96-0 1,2-dichloro-3-(2-chloro-4-bromophenoxy)propane 
• 86808-94-8 1,3-dichloro-2-(2-chloro-4-bromophenoxy)propane 
• 185527-66-6 methyl E-(3-chloro-4-hydroxyphenyl)acrylate 
• 313511-11-4 2-chloro-4-(1-hydroxy-4,4-dimethylcyclohexyl)phenol 
• 957127-58-1 2-chloro-4-((trimethylsilyl)ethynyl)phenol 
• 435287-53-9 1-[2-(4-bromo-2-chloro-phenoxy)-ethyl]-pyrrolidine 
• 869569-66-4 C₈H₇BrCl₂O 
• 1040236-29-0 C₁₄H₁₆BrNO₂ 
• 1040236-26-7 4-benzyl-7-bromo-1,4-benzoxazin-3-one 
• 876549-14-3 C₁₃H₆BrClN₂O₃ 

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