Product Name

  • Name

    4-Bromo-3,5-dihydroxybenzoic acid

  • EINECS 240-606-4
  • CAS No. 16534-12-6
  • Article Data14
  • CAS DataBase
  • Density 2.026 g/cm3
  • Solubility
  • Melting Point 274-276 °C
  • Formula C7H5BrO4
  • Boiling Point 387.1 °C at 760 mmHg
  • Molecular Weight 233.018
  • Flash Point 187.9 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 16534-12-6 (4-Bromo-3,5-dihydroxybenzoic acid)
  • Hazard Symbols IrritantXi
  • Synonyms a-Resorcylic acid, 4-bromo- (8CI);4-Bromo-3,5-resorcylic acid;NSC 151972;4-Bromo-3,5-dihydroxybenzoic acid;
  • PSA 77.76000
  • LogP 1.55850

Synthetic route

3,5-Dihydroxybenzoic acid
99-10-5

3,5-Dihydroxybenzoic acid

3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride; bromine for 2h; Heating;100%
With hydrogenchloride; bromine In water for 2h; Inert atmosphere; Schlenk technique; Reflux;99%
With hydrogenchloride; bromine In water for 2h; Reflux; Inert atmosphere;99%
3,5-Dihydroxybenzoic acid
99-10-5

3,5-Dihydroxybenzoic acid

A

3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

B

2-bromo-3,5-dihydroxybenzoic acid

2-bromo-3,5-dihydroxybenzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide; sodium bromide; tetraethoxy orthosilicate; 3-aminopropyltriethoxysilane In 1,4-dioxane; phosphate buffer for 19h;A n/a
B 91%
3,5-Dihydroxybenzoic acid
99-10-5

3,5-Dihydroxybenzoic acid

water
7732-18-5

water

bromine water

bromine water

3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

...Expand
ethanol
64-17-5

ethanol

3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

3,5-dihydroxy-4-bromobenzoic acid ethyl ester
350035-53-9

3,5-dihydroxy-4-bromobenzoic acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid for 12h; Reflux;100%
With sulfuric acid for 4h; Reflux;97%
With sulfuric acid for 24h; Reflux;96%
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

methyl 4-bromo-3,5-dimethoxybenzoate
26050-64-6

methyl 4-bromo-3,5-dimethoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone for 4.5h; Reflux;100%
With potassium carbonate In acetone for 12h; Reflux;90%
With potassium carbonate In acetone for 4h; Heating;76%
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

(methoxy)methyl 3,5-bis(methoxymethoxy)-4-bromobenzoate
167832-31-7

(methoxy)methyl 3,5-bis(methoxymethoxy)-4-bromobenzoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;89%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 48h;
methanol
67-56-1

methanol

3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

4-bromo-3,5-dihydroxy-benzoic acid methyl ester
34126-16-4

4-bromo-3,5-dihydroxy-benzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid for 16h; Reflux;99%
With thionyl chloride for 2h; Heating;96%
With sulfuric acid for 12h; Heating;96%
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

4-bromo-3,5-dihydroxy-benzoic acid methyl ester
34126-16-4

4-bromo-3,5-dihydroxy-benzoic acid methyl ester

Conditions
ConditionsYield
With thionyl chloride In methanol at 60℃; for 3h;99%
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

ethyl iodide
75-03-6

ethyl iodide

ethyl 4-bromo-3,5-diethoxybenzoate
149517-92-0

ethyl 4-bromo-3,5-diethoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 15 - 90℃; for 13h;99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;98%
With potassium carbonate In N,N-dimethyl-formamide at 50℃;93%
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

allyl bromide
106-95-6

allyl bromide

3,5-bis-allyloxy-4-bromo-benzoic acid allyl ester
355121-57-2

3,5-bis-allyloxy-4-bromo-benzoic acid allyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h;97%
With K2CO3 In water; N,N-dimethyl-formamide97%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

benzyl bromide
100-39-0

benzyl bromide

benzyl 3,5-bis(benzyloxy)-4-bromobenzoate
158585-09-2

benzyl 3,5-bis(benzyloxy)-4-bromobenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 4h;96%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 60℃; Inert atmosphere;89%
With potassium carbonate In N,N-dimethyl-formamide for 20h; Ambient temperature;75%
Me2SO4

Me2SO4

3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

methyl 4-bromo-3,5-dimethoxybenzoate
26050-64-6

methyl 4-bromo-3,5-dimethoxybenzoate

Conditions
ConditionsYield
95%
methylene chloride
74-87-3

methylene chloride

3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

4-bromo-3,5-dimethoxybenzoic acid
56518-42-4

4-bromo-3,5-dimethoxybenzoic acid

Conditions
ConditionsYield
Stage #1: 3,5-dihydroxy-4-bromobenzoic acid With sodium hydride In water at 70℃; for 0.5h; pH=8;
Stage #2: methylene chloride With sodium 4-dodecylbenzenesulfonate In methanol; water at 75℃; under 1500.15 Torr; for 1h; Temperature; pH-value; Pressure; Reagent/catalyst; Autoclave;		94.49%
ethyl bromide
74-96-4

ethyl bromide

3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

4-bromo-3,5-diethoxybenzoic acid
363166-41-0

4-bromo-3,5-diethoxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 20℃;92%
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

methyl 4-bromo-3,5-dimethoxybenzoate
26050-64-6

methyl 4-bromo-3,5-dimethoxybenzoate

Conditions
ConditionsYield
With potassium carbonate; dimethyl sulfate In acetone for 24h; Reflux; Inert atmosphere;92%
With potassium carbonate; dimethyl sulfate In acetone Reflux; Inert atmosphere;92%
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

isopropyl bromide
75-26-3

isopropyl bromide

C16H23BrO4

C16H23BrO4

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 50℃; for 72h;92%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 50℃; for 72h; Inert atmosphere;92%
Benzyloxymethyl chloride
3587-60-8

Benzyloxymethyl chloride

3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

(benzyloxy)methyl 3,5-bis((benzyloxy)methoxy)-4-bromobenzoate
1450741-52-2

(benzyloxy)methyl 3,5-bis((benzyloxy)methoxy)-4-bromobenzoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; Schlenk technique;87%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;87%
Dimethoxymethane
109-87-5

Dimethoxymethane

3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

(methoxy)methyl 3,5-bis(methoxymethoxy)-4-bromobenzoate
167832-31-7

(methoxy)methyl 3,5-bis(methoxymethoxy)-4-bromobenzoate

Conditions
ConditionsYield
Stage #1: Dimethoxymethane With acetyl chloride; zinc dibromide In dichloromethane at 0℃; for 0.5h;
Stage #2: 3,5-dihydroxy-4-bromobenzoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 13h;		86%
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

4-bromo-3,5-dimethoxymethoxybenzoic acid
167830-45-7

4-bromo-3,5-dimethoxymethoxybenzoic acid

Conditions
ConditionsYield
Stage #1: 3,5-dihydroxy-4-bromobenzoic acid; chloromethyl methyl ether With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 48h;
Stage #2: With sodium hydroxide In methanol at 70℃; for 3h;
Stage #3: With hydrogenchloride In methanol; water at 0℃; pH=5 - 6;		60%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 48h; Inert atmosphere;60%
diethyl sulfate
64-67-5

diethyl sulfate

3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

ethyl 4-bromo-3,5-diethoxybenzoate
149517-92-0

ethyl 4-bromo-3,5-diethoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone for 8h; Esterification; etherification; Heating;51%
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

benzylamine
100-46-9

benzylamine

N-Benzyl-4-bromo-3,5-dihydroxy-benzamide
675850-37-0

N-Benzyl-4-bromo-3,5-dihydroxy-benzamide

Conditions
ConditionsYield
39%
39%
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

methyl 4-bromo-3-hydroxy-5-methoxybenzoate
876170-40-0

methyl 4-bromo-3-hydroxy-5-methoxybenzoate

Conditions
ConditionsYield
With potassium carbonate; methyl iodide In N,N-dimethyl-formamide at 20℃; for 60h;13.1%
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
With potassium hydroxide beim Schmelzen;
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

4-bromo-3,5-dihydroxy-2,6-dinitro-benzoic acid
860757-51-3

4-bromo-3,5-dihydroxy-2,6-dinitro-benzoic acid

Conditions
ConditionsYield
With nitric acid
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

4-bromo-3,5-dimethoxybenzoic acid
56518-42-4

4-bromo-3,5-dimethoxybenzoic acid

Conditions
ConditionsYield
With sodium hydroxide
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

potash

potash

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

Conditions
ConditionsYield
beim Schmelzen;
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

3-({2,11,13,22-tetraoxa-1,12(1,3,2)-dibenzena-23(2,6)-pyridinabicyclo[10.10.1]tricosaphan-6,17-dien-15-yl}methyloxy)benzoic acid

3-({2,11,13,22-tetraoxa-1,12(1,3,2)-dibenzena-23(2,6)-pyridinabicyclo[10.10.1]tricosaphan-6,17-dien-15-yl}methyloxy)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 64 percent / conc. H2SO4 / 18 h / Heating
2.1: 97 percent / PPh3; diisopropyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C
3.1: 90 percent / diisobutylaluminium hydride / hexane; tetrahydrofuran / 2 h / 20 °C
4.1: 87 percent / imidazole / CH2Cl2 / 1 h / 20 °C
5.1: trimethylborate; n-BuLi / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
5.2: 81 percent / H2O
6.1: 92 percent / aq. Na2CO3; Ba(OH)2*H2O / Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O / 19 h / Heating
7.1: 92 percent / benzylidenebis(tricyclohexylphosphane)dichlororuthenium / CH2Cl2 / 48 h / 20 °C
8.1: 98 percent / Bu4NF*3H2O / tetrahydrofuran / 0.75 h / 20 °C
9.1: 87 percent / PPh3; diisopropyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C
10.1: 84 percent / LiOH / tetrahydrofuran; methanol; H2O / 4 h / 40 °C
View Scheme
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

2-[2,6-bis(pent-4-enyloxy)phenyl]-6-[2,6-bis(pent-4-enyloxy)-4-(tert-butyldimethylsilyloxymethyl)phenyl]pyridine
934990-38-2

2-[2,6-bis(pent-4-enyloxy)phenyl]-6-[2,6-bis(pent-4-enyloxy)-4-(tert-butyldimethylsilyloxymethyl)phenyl]pyridine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 64 percent / conc. H2SO4 / 18 h / Heating
2.1: 97 percent / PPh3; diisopropyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C
3.1: 90 percent / diisobutylaluminium hydride / hexane; tetrahydrofuran / 2 h / 20 °C
4.1: 87 percent / imidazole / CH2Cl2 / 1 h / 20 °C
5.1: trimethylborate; n-BuLi / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
5.2: 81 percent / H2O
6.1: 92 percent / aq. Na2CO3; Ba(OH)2*H2O / Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O / 19 h / Heating
View Scheme
3,5-dihydroxy-4-bromobenzoic acid
16534-12-6

3,5-dihydroxy-4-bromobenzoic acid

2-[2,6-bis(hex-5-enyloxy)phenyl]-6-[2,6-bis(hex-5-enyloxy)-4-(2-tetrahydropyranyloxymethyl)phenyl]pyridine
934991-07-8

2-[2,6-bis(hex-5-enyloxy)phenyl]-6-[2,6-bis(hex-5-enyloxy)-4-(2-tetrahydropyranyloxymethyl)phenyl]pyridine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 64 percent / conc. H2SO4 / 18 h / Heating
2.1: 80 percent / K2CO3; KI / dimethylformamide / 16 h / 70 °C
3.1: 87 percent / diisobutylaluminium hydride / hexane; tetrahydrofuran / 3 h / 20 °C
4.1: 88 percent / p-TsOH / CH2Cl2 / 16 h / 20 °C
5.1: trimethylborate; n-BuLi / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
5.2: 60 percent / H2O
6.1: 84 percent / aq. Na2CO3; Ba(OH)2*H2O / Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O / 19 h / Heating
View Scheme

4-Bromo-3,5-dihydroxybenzoic acid Specification

The Benzoicacid, 4-bromo-3,5-dihydroxy-, with the CAS registry number 16534-12-6, is also known as 4-Bromo-3,5-resorcylic acid. It belongs to the product categories of Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organic acids; Alcohols; Monomers; Polymer Science. Its EINECS number is 240-606-4. This chemical's molecular formula is C7H5BrO4 and molecular weight is 233.02. What's more, its systematic name is 4-bromo-3,5-dihydroxybenzoic acid. It is stable at common pressure and temperature, and it should be sealed and stored in a ventilated and dry place. Moreover, it should be protected from oxides and light.

Physical properties of Benzoicacid, 4-bromo-3,5-dihydroxy- are: (1)ACD/LogP: 2.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.53; (4)ACD/LogD (pH 7.4): -0.64; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 5.73; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 44.76 Å2; (13)Index of Refraction: 1.703; (14)Molar Refractivity: 44.63 cm3; (15)Molar Volume: 115 cm3; (16)Polarizability: 17.69×10-24cm3; (17)Surface Tension: 85.7 dyne/cm; (18)Density: 2.026 g/cm3; (19)Flash Point: 187.9 °C; (20)Enthalpy of Vaporization: 67.09 kJ/mol; (21)Boiling Point: 387.1 °C at 760 mmHg; (22)Vapour Pressure: 1.1E-06 mmHg at 25°C.

Uses of Benzoicacid, 4-bromo-3,5-dihydroxy-: it can be used to produce 4-Brom-3,5-dihydroxybenzoesaeure-methylester by heating. It will need reagent SOCl2 with the reaction time of 2 hours. The yield is about 96%.

Benzoicacid, 4-bromo-3,5-dihydroxy- can be used to produce 4-Brom-3,5-dihydroxybenzoesaeure-methylester by heating

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)InChI: InChI=1S/C7H5BrO4/c8-6-4(9)1-3(7(11)12)2-5(6)10/h1-2,9-10H,(H,11,12)
(2)InChIKey: NUTRHYYFCDEALP-UHFFFAOYSA-N
(3)Canonical SMILES: C1=C(C=C(C(=C1O)Br)O)C(=O)O

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