608-33-3

Basic information

• Product Name: 2,6-Dibromophenol
• Synonyms: 2,6-DIBROMOPHENOL;2,6-dibromo-pheno;2,6-DIBROMOPHENOL, 1000MG,NEAT;2 6-DIBROMOPHENOL 99% (HPLC);2,6-Dibromophenol98%;2,6-Dibromophenol,99%;Phenol, 2,6-dibromo-;Dibromophenol, 2,6-
• CAS NO: 608-33-3
• Molecular Formula: C₆H₄Br₂O
• Molecular Weight: 251.9
• EINECS: 210-161-0
• Product Categories: Aromatic Phenols;Alpha Sort;BromoVolatiles/ Semivolatiles;Chemical Class;D;DAlphabetic;DIA - DIC;Halogenated;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 608-33-3.mol
• Article Data: 22

Chemical Properties

• Melting Point: 53-56 °C(lit.)
• Boiling Point: 255-256 °C740 mm Hg(lit.)
• Flash Point: 255-256°C
• Appearance: White/Crystals or Needles
• Density: 1.8854 (rough estimate)
• Vapor Pressure: 0.009mmHg at 25°C
• Refractive Index: 1.5380 (estimate)
• Storage Temp.: Room temperature.
• PKA: 6.89±0.10(Predicted)
• Water Solubility: Soluble in ethanol and ether. Slightly soluble in water.
• BRN: 2043614
• CAS DataBase Reference: 2,6-Dibromophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dibromophenol(608-33-3)
• EPA Substance Registry System: 2,6-Dibromophenol(608-33-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 28-36/37-37/39-26-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 608-33-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 608-33-3 differently. You can refer to the following data:
1. 2,6-Dibromophenol is used in the production of 3,4,5-trimethoxybenzaldehyde and 2-(2,6-dibromophenoxy)ethylbromide.
2. 2,6-Dibromophenol is an off-flavor compound that is a metabolite of the spoilage bacteria Alicyclobacillus acidoterrestris. 2,6-Dibromophenol is a metabolic inhibitor and an auxin-like molecule.

General Description

2,6-Dibromophenol has been isolated from a luminous marine enteropneust, Balanoglossus biminiensis and is responsible for the characteristic ″iodoform-like″ odor of these animals.

Purification Methods

Distil the phenol under vacuum (at 10mm), then crystallise it from cold CHCl3 or from EtOH/water. [Beilstein 6 H 202, 6 I 106, 6 II 188, 6 III 755, 6 IV 1064.]

InChI:InChI=1/C6H4Br2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H

Synthetic route

3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
With quinoline; copper(I) oxide at 220℃; for 6h; Autoclave;	95%
With water at 165℃;
With sodium hydroxide at 165℃;

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (269409-70-3) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
Stage #1: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol With N-Bromosuccinimide In dichloromethane at 20℃; for 12h; Stage #2: With water In dimethyl sulfoxide at 120℃; for 24h;	93%
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / dichloromethane / 12 h / 20 °C / Inert atmosphere 2: dimethyl sulfoxide; water / 24 h / 120 °C / Inert atmosphere View Scheme

2,6-Dibrom-methylammonium-phenolat (100477-81-4) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
With sulfuric acid Heating;	87%

2,6-Dibromo-phenol; compound with tert-butylamine (100782-00-1) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
With sulfuric acid Heating;	87%

2-hydroxybromobenzene (95-56-7) → 2,6-dibromophenol (608-33-3) + 2,4,6-tribromophenol (118-79-6)

Conditions	Yield
With N-Bromosuccinimide; diisopropylamine In dichloromethane for 1h; Ambient temperature;	A 80% B 5.7 % Chromat.

2,6-dibromophenyl dimethylcarbamate (1375931-46-6) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
With hydrazine hydrate at 60℃; for 2h; Sealed tube; regioselective reaction;	80%

phenol (108-95-2) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
With N-Bromosuccinimide; diisopropylamine In dichloromethane at 23℃; for 4h; Schlenk technique;	79%
With N-Bromosuccinimide; diisopropylamine In dichloromethane at 20℃; for 1h;	72%
With N-Bromosuccinimide; diisopropylamine In dichloromethane at 20℃; Inert atmosphere;	69%
With bromine; tert-butylamine
With tetra-N-butylammonium tribromide In methanol; dichloromethane at 20℃; for 1h;

2,4,6-tribromophenol (118-79-6) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
With Hβ-zeolite; sodium sulfite In methanol for 48h; Heating;	57%
With potassium hydrogensulfate; sodium sulfite In methanol for 48h; Heating;	45%
With aluminium; sodium hydroxide In water at 25℃; for 16h;	14 %Spectr.

piperidine (110-89-4) + 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
at 150 - 165℃;

quinoline (91-22-5) + 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
at 190 - 200℃;

ethanol (64-17-5) + 2,6-dibromo-4-aminophenol (609-21-2) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
With sulfuric acid; sodium nitrite; benzene Kochen der erhaltenen Diazoniumsalz-Loesung;

2,2,6,6-tetrabromo-cyclohexanone (29170-71-6) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
at 120 - 130℃;
at 120 - 130℃;

2,6-dibromoaniline (608-30-0) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
Diazotization.Erhitzen des sauren Diazoniumsulfats mit Schwefelsaeure;

2,6-dibromo-4-aminophenol (609-21-2) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
Diazotization.Kochen des Reaktionsprodukts mit Alkohol und konz. Schwefelsaeure;

2-(3,5,3',5'-tetrabromo-4,4'-dihydroxy-benzhydryl)-benzoic acid (28818-25-9) → 2,6-dibromophenol (608-33-3) + 1,3-dibromo-2-hydroxyanthraquinone (861075-99-2)

Conditions	Yield
With sulfuric acid bei der Destillation;

3,5-dibromo-2-methoxybenzoic acid (13130-23-9) + aniline hydrochloride (142-04-1) + aniline (62-53-3) → 2,4-dibromophenol (615-58-7) + 2-hydroxybromobenzene (95-56-7) + 2,6-dibromophenol (608-33-3)

Conditions	Yield
at 220℃;

2,6-dibromoanisole (38603-09-7) + aniline hydrochloride (142-04-1) + aniline (62-53-3) → 2-hydroxybromobenzene (95-56-7) + 2,6-dibromophenol (608-33-3) + phenol (108-95-2)

Conditions	Yield
at 220℃;

phenol (108-95-2) → 2-hydroxybromobenzene (95-56-7) + 2,6-dibromophenol (608-33-3)

Conditions	Yield
With sulfuric acid at 100 - 110℃; Behandeln des Reaktionsprodukts mit rauchender Schwefelsaeure in Nitrobenzol <10grad und mit Brom und anschliessendes Erhitzen mit Wasserdampf auf 175-180grad;
With sulfuric acid at 100 - 110℃; Behandeln des Reaktionsprodukts mit rauchender Schwefelsaeure in Nitrobenzol unterhalb 10grad und mit Brom und anschliessendes Kochen mit Wasser;

2-hydroxybromobenzene (95-56-7) → 4-bromo-phenol (106-41-2) + 2,4-dibromophenol (615-58-7) + 2,6-dibromophenol (608-33-3) + phenol (108-95-2)

Conditions	Yield
With trifluorormethanesulfonic acid; tetramethylammonium bromide	A 32 % Chromat. B 29 % Chromat. C 3 % Chromat. D 24 % Chromat.

phenol (108-95-2) → 4-bromo-phenol (106-41-2) + 2,4-dibromophenol (615-58-7) + 2-hydroxybromobenzene (95-56-7) + 2,6-dibromophenol (608-33-3)

Conditions	Yield
With trifluorormethanesulfonic acid; bromine	A 60 % Chromat. B 13 % Chromat. C 4 % Chromat. D 1 % Chromat.
With monobromoisocynaurate In dichloromethane for 1h; Product distribution; Further Variations:; Reagents; Solvents; reaction time; Heating;

phenol (108-95-2) → 4-bromo-phenol (106-41-2) + 2,4-dibromophenol (615-58-7) + 2-hydroxybromobenzene (95-56-7) + 2,6-dibromophenol (608-33-3) + 2,4,6-tribromophenol (118-79-6)

Conditions	Yield
With N-Bromosuccinimide; diisopropylamine In dichloromethane for 1h; Product distribution; Mechanism; Ambient temperature; also 2-substituted phenols and other bromination agent; var. primary and secondary amines and conditions;	A 0.8 % Chromat. B 1.4 % Chromat. C 3.2 % Chromat. D 81.8 % Chromat. E 10.7 % Chromat.

sulfuric acid (7664-93-9) + 3,3-bis(3,5-dibromo-4-hydroxyphenyl)phthalide (76-62-0) → 2,6-dibromophenol (608-33-3) + 1,3-dibromo-2-hydroxyanthraquinone (861075-99-2)

ethanol (64-17-5) + sulfuric acid (7664-93-9) + 4-Diazo-2,6-dibromo-2,5-cyclohexadienone (38676-25-4) → 2,6-dibromophenol (608-33-3)

tetrachloromethane (56-23-5) + 2.6-dibromo-4-tert.-pentyl-phenol → 2,6-dibromophenol (608-33-3)

Conditions	Yield
With aluminium trichloride

2.6-dibromo-quinone-(1.4)-diazide-(4) → 2,6-dibromophenol (608-33-3)

Conditions	Yield
With ethanol; copper

acidic 2.6-dibromo-benzenediazonium sulfate → 2,6-dibromophenol (608-33-3)

Conditions	Yield
With water Sonnenlicht;

hydrogenchloride (7647-01-0) + 3,5-dibromo-2-methoxybenzoic acid (13130-23-9) → 2,4-dibromophenol (615-58-7) + 2-hydroxybromobenzene (95-56-7) + 2,6-dibromophenol (608-33-3)

Conditions	Yield
at 220℃;

hydrogenchloride (7647-01-0) + 3,5-dibromo-4-methoxybenzoic acid (4073-35-2) → 2,4-dibromophenol (615-58-7) + 2-hydroxybromobenzene (95-56-7) + 2,6-dibromophenol (608-33-3)

Conditions	Yield
at 200℃;

hydrogenchloride (7647-01-0) + 2,4-dibromoanisole (21702-84-1) → 4-bromo-phenol (106-41-2) + 2,4-dibromophenol (615-58-7) + 2-hydroxybromobenzene (95-56-7) + 2,6-dibromophenol (608-33-3)

Conditions	Yield
at 220℃;

2,6-dibromophenol (608-33-3) + acetic anhydride (108-24-7) → 1-acetoxy-2,6-dibromobenzene (28165-72-2)

Conditions	Yield
With pyridine	100%
With pyridine at 80℃; for 3h;	98%
With pyridine

2,6-dibromophenol (608-33-3) + 1-Bromo-2-chloroethane (107-04-0) → (2,6-dibromophenyl) (2-chloroethyl) ether (281678-66-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	100%
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 4h;	97%

2,6-dibromophenol (608-33-3) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyldimethylsilyl 2,6-dibromophenyl ether (1089665-82-6)

Conditions	Yield
With 1H-imidazole In tetrahydrofuran at 20℃; for 0.583333h; Inert atmosphere;	100%

2,6-dibromophenol (608-33-3) + 3-(dimethylamino)propyl chloride hydrochloride (5407-04-5) → C11H15Br2NO

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; Inert atmosphere; Schlenk technique;	100%

2,6-dibromophenol (608-33-3) + benzyl bromide (100-39-0) → 2-(Benzyloxy)-1,3-dibromobenzene (122110-76-3)

Conditions	Yield
With potassium carbonate In butanone for 1.5h; Heating / reflux;	99%
Stage #1: 2,6-dibromophenol; benzyl bromide With potassium carbonate In acetonitrile at 20℃; for 24h; Heating / reflux; Stage #2: With piperidine In acetonitrile at 60℃; for 1h;	99%
With potassium carbonate; sodium iodide In acetonitrile for 16h; Reflux;	82%
With potassium carbonate In acetone for 48h; Heating;	80%
With sodium hydride In mineral oil at 80℃;

2,6-dibromophenol (608-33-3) + chloromethyl methyl ether (107-30-2) → 1,3-dibromo-2-(methoxymethoxy)benzene (142273-81-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran; acetic acid methyl ester at 0 - 20℃; for 2h;	99%
With triethylamine In dichloromethane at 0℃; for 7h; Inert atmosphere;	99%
Stage #1: 2,6-dibromophenol With sodium hydride In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: chloromethyl methyl ether In tetrahydrofuran at 25℃; for 2h;	97%

chloro-trimethyl-silane (75-77-4) + 2,6-dibromophenol (608-33-3) → 2-bromo-6-(trimethylsilyl)phenol (58144-49-3)

Conditions	Yield
Stage #1: chloro-trimethyl-silane; 2,6-dibromophenol With sodium hydride In tetrahydrofuran at 0℃; for 4h; Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 5h; Further stages.;	99%

2,6-dibromophenol (608-33-3) + methyl iodide (74-88-4) → 2,6-dibromoanisole (38603-09-7)

Conditions	Yield
With potassium carbonate Inert atmosphere;	99%
With potassium carbonate In acetone Heating;	98%
Stage #1: 2,6-dibromophenol With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: methyl iodide In acetone at 60℃; for 3h;	98%

2,6-dibromophenol (608-33-3) + 3,5-bis[3,5-bis(benzyloxy)benzyloxy]benzyl bromide (129536-41-0) → C55H46Br2O7 (1332878-07-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; Williamson synthesis; Inert atmosphere;	99%

2,6-dibromophenol (608-33-3) + 2-(N-tert-butoxycarbonylamino)ethanol (26690-80-2) → tert-butyl (2-(2,6-dibromophenoxy)ethyl)carbamate

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 24h;	99%

2,6-dibromophenol (608-33-3) + tetramethylammonium trifluoromethylselenate(0) (75264-92-5) → 7-bromo-2,2-difluorobenzo[d][1,3]oxaselenole

Conditions	Yield
With potassium fluoride; 1,10-Phenanthroline; copper(l) cyanide In N,N-dimethyl-formamide at 100℃; for 3h; Inert atmosphere; Glovebox; Sealed tube;	99%

2,6-dibromophenol (608-33-3) + 1-dodecylbromide (143-15-7) → 2,6-dibromo(dodecyloxy)benzene

Conditions	Yield
With potassium carbonate In acetonitrile for 20h; Reflux;	98%

2,6-dibromophenol (608-33-3) + naphthalene-2-boronic acid (32316-92-0) → 2-(naphthalen-2-yl)-6-(naphthalen-7-yl)phenol (1187669-96-0)

Conditions	Yield
With potassium phosphate; palladium diacetate; ruphos In water; toluene at 100℃; for 16h; Suzuki coupling; Inert atmosphere;	98%

tetraethylene glycol di(p-toluenesulfonate) (37860-51-8) + 2,6-dibromophenol (608-33-3) → C20H22Br4O5

Conditions	Yield
With cesium fluoride In acetonitrile at 20℃; for 6h; Substitution; Heating;	97%

2,6-dibromophenol (608-33-3) + 3,5-bis(benzyloxy)benzyl bromide (24131-32-6) → C27H22Br2O3 (1332878-06-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; Williamson synthesis; Inert atmosphere;	97%

2,6-dibromophenol (608-33-3) → 2,6-dibromoanisole (38603-09-7)

Conditions	Yield
With potassium carbonate; dimethyl sulfate In n-heptane; ethyl acetate; acetonitrile	96%
With diazomethane; diethyl ether

2,6-dibromophenol (608-33-3) + tert-butyl N-(2-chloroethyl)carbamate (71999-74-1) → tert-butyl (2-(2,6-dibromophenoxy)ethyl)carbamate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; Inert atmosphere; Schlenk technique;	96%

1,4-dibromo-butane (110-52-1) + 2,6-dibromophenol (608-33-3) → 1,3-dibromo-2-(4-bromobutoxy)benzene (1094627-64-1)

Conditions	Yield
Stage #1: 2,6-dibromophenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; Schlenk technique; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; Schlenk technique;	95%
With sodium hydroxide In water for 17h; Heating / reflux;

2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione (118-29-6) + 2,6-dibromophenol (608-33-3) → C15H9Br2NO3

Conditions	Yield
With sulfuric acid In tetrahydrofuran at 20℃; Cooling with ice;	95%

2,6-dibromophenol (608-33-3) + 8-tosyloxy-3,6-dioxaoctanol (77544-68-4) → 1,3-dibromo-2-(9-hydroxy-1,4,7-trioxanonyl)benzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 35h;	94%

2,6-dibromophenol (608-33-3) + 1-bromo-5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluorodecane (181997-60-4) → 2,6-dibromo-(5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluorodecyloxy)benzene

Conditions	Yield
With potassium carbonate In acetonitrile for 20h; Reflux;	94%

2,6-dibromophenol (608-33-3) + 3,5-bis[3,5-bis[3,5-bis(benzyloxy)benzyloxy]benzyloxy]benzyl bromide (137472-17-4) → C111H94Br2O15

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; Williamson synthesis; Inert atmosphere;	94%

2,6-dibromophenol (608-33-3) + cesium trifluoromethanethiolate → 7-bromo-2,2-difluorobenzo[d][1,3]oxathiole

Conditions	Yield
With 1,10-Phenanthroline; copper(I) thiocyanate; cesium fluoride In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; Glovebox; Sealed tube;	94%

Isopropenyl acetate (108-22-5) + 2,6-dibromophenol (608-33-3) → 1-acetoxy-2,6-dibromobenzene (28165-72-2)

Conditions	Yield
With methanesulfonic acid In 1,2-dichloro-ethane for 0.5h; Heating;	93%

2,6-dibromophenol (608-33-3) + sodium chlorodifluoroacetate (1895-39-2) → 1,3-dibromo-2-difluoromethoxy-benzene (1182728-50-2)

Conditions	Yield
In water; N,N-dimethyl-formamide at 100℃; for 3h;	93%
With potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 3h;	93%

2,6-dibromophenol (608-33-3) + ethyl bromoacetate (105-36-2) → ethyl 2-(2,6-dibromophenoxy)acetate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;

2,6-dibromophenol (608-33-3) → 2,6-dibromo-4-iodophenol (187407-15-4)

Conditions	Yield
With N-iodo-succinimide In acetonitrile at 20℃; for 4h;	92%
With N-iodo-succinimide In acetonitrile at 20℃; for 4h;	89%

2,6-dibromophenol (608-33-3) + 2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (16977-78-9, 85193-55-1, 86651-32-3, 86651-40-3) → 2-(2,6-dibromophenoxy)ethyl 2,3,4,6-tetra-O-acetyl-D-glucopyranoside (1207987-62-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 20h; Inert atmosphere;	92%

Upstream product

• 91-22-5 quinoline 
• 3337-62-0 3,5-dibromo-4-hydroxybenzoic acid 
• 608-30-0 2,6-dibromoaniline 
• 108-95-2 phenol 
• 95-56-7 2-hydroxybromobenzene 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 38603-09-7 2,6-dibromoanisole 
• 87448-02-0 2,6-dibromo-[1,4]benzoquinone-4-benzoylhydrazone 
• 118-79-6 2,4,6-tribromophenol 
• 100477-81-4 2,6-Dibrom-methylammonium-phenolat 
• 13130-23-9 3,5-dibromo-2-methoxybenzoic acid 
• 142-04-1 aniline hydrochloride 
• 62-53-3 aniline 

Downstream Products

• 69-72-7 salicylic acid 
• 6315-70-4 3-(3,5-dibromo-4-hydroxy-phenyl)-3-phenyl-phthalide 
• 28165-72-2 1-acetoxy-2,6-dibromobenzene 
• 52751-69-6 4-benzyl-2,6-dibromo-phenol 
• 855358-86-0 2,6-dibromo-4-(2-bromo-benzyl)-phenol 
• 72764-02-4 2,6-dibromophenol allyl ether 
• 71581-85-6 2-(3,5-Dibromo-4-hydroxy-benzoyl)-chromen-4-one 
• 117923-78-1 2,6-dibromoanisole-α-13C 
• 79020-64-7 cis-1,4-bis(2,6-dibromophenoxy)cyclopent-2-ene 
• 576-26-1 2.6-dimethylphenol 
• 13319-71-6 2-bromo-6-methylphenol 
• 32750-14-4 3,3'-dimethyl-[1,1'-biphenyl]-2,2'-diol 
• 95-48-7 ortho-cresol 
• 2362-50-7 thianthrene-5-oxide 

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