3337-62-0

Basic information

• Product Name: 3,5-Dibromo-4-hydroxybenzoic acid
• Synonyms: 3,5-dibromo-4-hydroxy-benzoicaci;Benzoic acid, 3,5-dibromo-4-hydroxy-;Bromoxynylbenzoic acid;RARECHEM AL BO 0009;TIMTEC-BB SBB006717;LABOTEST-BB LT00453976;4-HYDROXY-3,5-DIBROMOBENZOIC ACID;3',5'-DIBROMO-4-HYDROXYBENZOIC ACID
• CAS NO: 3337-62-0
• Molecular Formula: C₇H₄Br₂O₃
• Molecular Weight: 295.91
• EINECS: 222-075-0
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids;Acids & Esters;Bromine Compounds;Phenols;alcohol| carboxylic acid| alkyl bromide
• Mol File: 3337-62-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 271-274 °C
• Boiling Point: 342 ºC at 760 mmHg
• Flash Point: 160.6 ºC
• Appearance: white fine crystalline powder
• Density: 2.0591 (rough estimate)
• Vapor Pressure: 2.98E-05mmHg at 25°C
• Refractive Index: 1.4947 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 3.79±0.10(Predicted)
• BRN: 2416147
• CAS DataBase Reference: 3,5-Dibromo-4-hydroxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dibromo-4-hydroxybenzoic acid(3337-62-0)
• EPA Substance Registry System: 3,5-Dibromo-4-hydroxybenzoic acid(3337-62-0)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 3337-62-0(Hazardous Substances Data)

Usage

Uses

3,5-Dibromo-4-hydroxybenzoic Acid is an intermediate used to prepare benzbromarone (B185200) which is a uricosuric agent used in the treatment of gout and hyperuricemia.

Definition

ChEBI: A monohydroxybenzoic acid that is p-salicylic acid with bromo- substituents at C-3 and C-5 of the benzene ring.

InChI:InChI=1/C7H4Br2O3/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,10H,(H,11,12)/p-1

Synthetic route

4-hydroxy-benzoic acid (99-96-7) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
With hydrogen bromide; dihydrogen peroxide In 1,2-dichloro-ethane at 45℃; for 3h;	97%
With bromine; calcium bromide In water at 25℃; for 0.25h; regioselective reaction;	94%
With bromine In water at 20℃; for 0.166667h;	89%

methyl 3,5-dibromo-4-hydroxybenzoate (41727-47-3) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
With water; sodium hydroxide at 60℃; for 4h;	94%
With sodium hydroxide

3-bromo-4-hydroxy-benzoic acid (14348-41-5) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) + 2,4,6-tribromophenol (118-79-6)

Conditions	Yield
With water; bromine

3,5-dibromo-4-methoxybenzoic acid (4073-35-2) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
With hydrogen iodide

acetic acid-(2,6-dibromo-4-methyl-phenyl ester) (67201-41-6) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
With chromic acid; acetic acid Hydrolyse des Reaktionsproduktes;

2,6-dibromo-4-(trifluoromethyl)phenol (35852-57-4) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
With sodium hydroxide

4-hydroxy-benzoic acid (99-96-7) → 3-bromo-4-hydroxy-benzoic acid (14348-41-5) + 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
With bromine; potassium bromide In water at 25℃; Rate constant; Product distribution; var. pH;
With N-Bromosuccinimide; 1-n-butyl-3-methylimidazolim bromide for 0.05h; Ionic liquid;
With [VO((R,R)-N,N-disalicylidenecyclohexane-1,2-diamine-2H)(methanol)]ClO4; dihydrogen peroxide; potassium bromide In acetonitrile at 60 - 80℃; for 15h; High-pressure reactor;
Stage #1: 4-hydroxy-benzoic acid In acetonitrile at 20℃; for 0.0833333h; Stage #2: With N-Bromosuccinimide In acetonitrile at 20℃; for 48h;

3,3-bis-(4-acetoxy-3,5-dibromo-phenyl)-phthalide (104541-40-4) + acetic acid (64-19-7) + chromic acid → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
durch Verseifung;

acetic acid (64-19-7) + 4-hydroxy-benzoic acid (99-96-7) + bromine (2 mol ) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

iodine (7553-56-2) + acetic acid (64-19-7) + 4-hydroxy-benzoic acid (99-96-7) + bromine (2 mol ) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

4-hydroxy-benzoic acid (99-96-7) + bromine vapour (2 mol ) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

3-bromo-4-hydroxy-benzoic acid (14348-41-5) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) + 2.4.6-tribromo-phenyl

Conditions	Yield
bei Bromierung;

3.5-dibromo-4-oxy-benzaldehyde → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
With potassium hydroxide man gibt waessr. KMnO4-Loesung hinzu;

3.5-dibromo-anisacidic sodium → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
With calcium oxide bei der Destillation;

2,6-dibromo-4-(trifluoromethyl)phenol (35852-57-4) + aqueous NaOH → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

4,4'-diacetoxy-3,5,3',5'-tetrabromo-biphenyl (574706-24-4) + acetic acid (64-19-7) + CrO3 → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
nachfolgend Hydrolyse;

3,5-dibromo-4-methoxy-benzoic acid ; sodium salt + CaO → methyl 3,5-dibromo-4-methoxybenzoate (22812-61-9) + 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

hydrogenchloride (7647-01-0) + 1-(4-acetoxy-3,5-dibromo-phenyl)-propan-1-one + isopentyl nitrite (110-46-3) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) + 2-hydroxyimino-1-<3.5-dibromo-4-hydroxy-phenyl>-propanone-(1)

Conditions	Yield
at 60 - 70℃;

methyl 4-hydroxylbenzoate (99-76-3) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; bromine 2: aq. NaOH solution View Scheme

4-trifluoromethylphenylamine (455-14-1) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: ueber die Diazonium-Verbindung 2: water; bromine 3: aq. NaOH solution View Scheme

4-hydroxybenzotrifluoride (402-45-9) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; bromine 2: aq. NaOH solution View Scheme

p-nitrobenzotrifluoride (402-54-0) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: tin (II)-chloride; aq.-ethanolic hydrochloric acid 2: ueber die Diazonium-Verbindung 3: water; bromine 4: aq. NaOH solution View Scheme

p-nitrobenzylidyne tribromide (14505-17-0) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: SbF3 / 100 °C 2: tin (II)-chloride; aq.-ethanolic hydrochloric acid 3: ueber die Diazonium-Verbindung 4: water; bromine 5: aq. NaOH solution View Scheme

1-dibromomethyl-4-nitro-benzene (619-75-0) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: aqueous NaOBr solution 2: SbF3 / 100 °C 3: tin (II)-chloride; aq.-ethanolic hydrochloric acid 4: ueber die Diazonium-Verbindung 5: water; bromine 6: aq. NaOH solution View Scheme

3,5-dibromo-4-hydroxybenzamide (3037-56-7) → 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0)

Conditions	Yield
With amidase from microbacterium imperiale CBS 498-74; water at 35℃; pH=5.5; Temperature; pH-value; Enzymatic reaction;

3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) + acetic anhydride (108-24-7) → 4-acetoxy-3,5-dibromobenzoic acid (72415-59-9)

Conditions	Yield
With sulfuric acid In dichloromethane at 35℃; for 5h;	100%

3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → 3,5-dibromo-4-hydroxy-benzoyl chloride (77823-55-3)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide for 2h; Ambient temperature;	96%
With thionyl chloride
With thionyl chloride for 6h; Heating / reflux;

methanol (67-56-1) + 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → methyl 3,5-dibromo-4-hydroxybenzoate (41727-47-3)

Conditions	Yield
With acetyl chloride for 18h; Ambient temperature;	95%
With sulfuric acid

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℃;

3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → 2,3,5,6-tetrabromo-1,4-benzoquinone oxime (1400881-33-5)

Conditions	Yield
With sodium nitrite In acetic acid at 20℃; for 4h;	95%

3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) + 5-(2,5-dimethylphenoxy)-2,2-dimethylpentan-1-amine → 3,5-dibromo-N-(5-(2,5-dimethylphenoxy)-2,2-dimethylpentyl)-4-hydroxybenzamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h;	54.6%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h;	51.3%

3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) + butan-1-ol (71-36-3) → butyl 3,5-di-bromo-4-hydroxybenzoate (75254-69-2)

Conditions	Yield
With sulfuric acid Fischer-Speier Esterification; Reflux;	53%

3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → 2,3,6-tribromo-4-hydroxybenzoic acid (1400881-30-2)

Conditions	Yield
With bromine In sulfuric acid at 20 - 45℃;	35%

2,3-Dihydro-1H-4-oxa-1,5-diaza-naphthalene (1112193-37-9) + 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → (3,5-dibromo-4-hydroxy-phenyl)-(2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone (1198153-12-6)

Conditions	Yield
Stage #1: 3,5-dibromo-4-hydroxybenzoic acid With thionyl chloride In ISOPROPYLAMIDE at -5℃; for 0.5h; Stage #2: 2,3-Dihydro-1H-4-oxa-1,5-diaza-naphthalene In ISOPROPYLAMIDE at -5 - 20℃; for 15.3333h;	31%

3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) + 2-amino-phenol (95-55-6) → 2-(3′,5′-dibromo-4′-hydroxyphenyl)-1,3-benzoxazole (1004983-96-3)

Conditions	Yield
With toluene-4-sulfonic acid In xylene for 18h; Heating;	17%

ethyl 2-oximinooxamate (1217428-98-2) + 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → Ethyl 5-(3,5-dibromo-4-hydroxyphenyl)-1,2,4-oxadiazole-3-carboxylate (1191254-12-2)

Conditions	Yield
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20 - 90℃;	12%
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20 - 90℃; for 7h;	12%

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) + 3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → 3,5-dibromo-4-hydroxy-benzoic acid ethyl ester (55771-81-8)

Conditions	Yield
With mineral acid

3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → 3,4,5-trihydroxybenzoic acid (149-91-7)

Conditions	Yield
With barium dihydroxide; water at 175℃; im Kupferkessel;
With potassium hydroxide; copper(I) sulfate; water; copper(II) sulfate at 150℃;

3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → 3,5-dibromo-4-methoxybenzoic acid (4073-35-2)

Conditions	Yield
durch Methylierung;

3,5-dibromo-4-hydroxybenzoic acid (3337-62-0) → 2-bromo-4,6-dinitrophenol (2316-50-9)

Conditions	Yield
bei der Nitrierung;

Upstream product

• 14348-41-5 3-bromo-4-hydroxy-benzoic acid 
• 4073-35-2 3,5-dibromo-4-methoxybenzoic acid 
• 41727-47-3 methyl 3,5-dibromo-4-hydroxybenzoate 
• 35852-57-4 2,6-dibromo-4-(trifluoromethyl)phenol 
• 99-96-7 4-hydroxy-benzoic acid 
• 64-19-7 acetic acid 
• 7553-56-2 iodine 
• 3037-56-7 3,5-dibromo-4-hydroxybenzamide 
• 14505-17-0 p-nitrobenzylidyne tribromide 
• 402-54-0 p-nitrobenzotrifluoride 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 7647-01-0 hydrogenchloride 
• 110-46-3 isopentyl nitrite 
• 574706-24-4 4,4'-diacetoxy-3,5,3',5'-tetrabromo-biphenyl 

Downstream Products

• 608-33-3 2,6-dibromophenol 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 4073-35-2 3,5-dibromo-4-methoxybenzoic acid 
• 2316-50-9 2-bromo-4,6-dinitrophenol 
• 793663-18-0 2,6-dibromo-[1,4]benzoquinone-4-oxime 
• 77823-55-3 3,5-dibromo-4-hydroxy-benzoyl chloride 
• 98278-83-2 2,3,5,6-tetrabromo-4-hydroxybenzoic acid 
• 72415-59-9 4-acetoxy-3,5-dibromobenzoic acid 
• 19643-45-9 2,6-dibromo-1,4-benzoquinone 
• 91203-82-6 4-hydroxy-<3,5-2H2>benzoic acid 
• 118-79-6 2,4,6-tribromophenol 
• 99-96-7 4-hydroxy-benzoic acid 
• 1191254-12-2 Ethyl 5-(3,5-dibromo-4-hydroxyphenyl)-1,2,4-oxadiazole-3-carboxylate 
• 55771-81-8 3,5-dibromo-4-hydroxy-benzoic acid ethyl ester 

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