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585-76-2

Basic Information
CAS No.: 585-76-2
Name: 3-Bromobenzoic acid
Article Data: 169
Cas Database
Molecular Structure:
Molecular Structure of 585-76-2 (3-Bromobenzoic acid)
Formula: C7H5BrO2
Molecular Weight: 201.019
Synonyms: Benzoic acid, m-bromo- (8CI);m-Bromobenzoic acid;Benzoic acid, m-bromo-;Benzoic acid, 3-bromo-;
EINECS: 209-562-3
Density: 1.701 g/cm3
Melting Point: 154-158 °C
Boiling Point: 308.2 °C at 760 mmHg
Flash Point: 140.2 °C
Solubility: 0.54 g/L (32 °C) in water
Appearance: White to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38-37/38-36
Safety: 26-36-37/39
Transport Information: N/A
PSA: 37.30000
LogP: 2.14730
Synthetic route
6952-59-6

3-cyanobromobenzene

585-76-2

m-bromobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; carbon monoxide; bis(benzonitrile)palladium(II) dichloride; triphenylphosphine In xylene at 90℃; for 4h; Hydrolysis;100%
With sodium hydroxide
3132-99-8

m-bromobenzoic aldehyde

585-76-2

m-bromobenzoic acid

Conditions
ConditionsYield
With Oxone In N,N-dimethyl-formamide at 20℃; for 3h;97%
Stage #1: m-bromobenzoic aldehyde With sodium dihydrogenphosphate In tetrahydrofuran; water at 20℃; for 0.166667h;
Stage #2: With sodium chlorite; dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 3h;
95%
With sodium chlorite; disodium hydrogenphosphate; dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 3h; Cooling with ice;95%
618-89-3

methyl 3-bromobenzoate

585-76-2

m-bromobenzoic acid

Conditions
ConditionsYield
With iodine; aluminium In acetonitrile at 80℃; for 18h;97%
With potassium hydroxide In methanol at 35℃; for 0.0833333h;80%
591-17-3

meta-bromotoluene

585-76-2

m-bromobenzoic acid

Conditions
ConditionsYield
With oxygen; pyridinium chlorochromate In water at 120℃; under 45004.5 Torr; for 2h;95%
With Oxone; potassium bromide In dichloromethane; water at 20℃; for 24h; visible light irradiation;93%
With oxygen; Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Green chemistry;93%
115665-95-7, 15795-14-9

3-bromo-β-nitro-styrene

585-76-2

m-bromobenzoic acid

Conditions
ConditionsYield
With Amberlyst A-26 (OH-); dihydrogen peroxide In 1,4-dioxane at 20℃; for 9h;95%
10075-50-0

5-bromo-1H-indole

A

201227-38-5

5-bromo-1H-indazole-3-carboxaldehyde

B

585-76-2

m-bromobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride; water; sodium nitrite In N,N-dimethyl-formamide at 0 - 50℃; for 5h; Inert atmosphere;A 94%
B n/a
65-85-0

benzoic acid

585-76-2

m-bromobenzoic acid

Conditions
ConditionsYield
With sodium bromate; potassium sulfate; sulfuric acid In water at 85 - 90℃; for 1.5h; regioselective reaction;93.7%
With sulfuric acid; bromine; mercury(II) oxide In tetrachloromethane for 2.5h; Heating;79%
With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid at 25℃; for 44h; Bromination;78%
15852-73-0

(3-Bromophenyl)methanol

585-76-2

m-bromobenzoic acid

Conditions
ConditionsYield
With [2,2]bipyridinyl; Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; acetic acid at 80℃; under 760.051 Torr; for 3h;91%
With Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;89%
With tert.-butylhydroperoxide at 100℃; for 5h;80%
35309-72-9

3-bromo-N,N-diisopropylbenzamide

A

585-76-2

m-bromobenzoic acid

B

35306-75-3

3-bromobenzoic acid isopropylamide

Conditions
ConditionsYield
With hydrogenchloride; zinc(II) chloride at 160℃; for 72h;A 90%
B 8%
339094-04-1

benzyl 3-bromobenzoic acid

585-76-2

m-bromobenzoic acid

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.166667h; chemoselective reaction;90%
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Specification

The IUPAC name of this chemical is 3-bromobenzoic acid. With the CAS registry number 585-76-2, it is also named as Benzoic acid, 3-bromo-. The product's categories are Blocks; Carboxes; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Benzoic Acid Derivative; Acids & Esters; Bromine Compounds; C7; Carbonyl Compounds; Carboxylic Acids. It is white to light yellow crystal powder which is soluble in alcohol and ether.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.71; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.03; (4)ACD/LogD (pH 7.4): -0.3; (5)ACD/BCF (pH 5.5): 1.41; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 14.78; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.608; (13)Molar Refractivity: 40.87 cm3; (14)Molar Volume: 118.1 cm3; (15)Polarizability: 16.2×10-24 cm3; (16)Surface Tension: 53.7 dyne/cm; (17)Enthalpy of Vaporization: 57.95 kJ/mol; (18)Vapour Pressure: 0.0003 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 199.947292; (21)MonoIsotopic Mass: 199.947292; (22)Topological Polar Surface Area: 37.3; (23)Heavy Atom Count: 10; (24)Complexity: 136.

Preparation of 3-Bromobenzoic acid: It can be obtained by m-bromotoluene through the oxidation of potassium permanganate. Mixing the m-bromotoluene, potassium hydroxide and water and heating to boiling. Adding potassium permanganate slowly, then refluxing 4h. After filtrate and acidification, filtering to get the crude. Using ammonia to disolve the crude in ethanol, and then using hydrochloric acid to acidize. Finally, after filtration and washing, we can get the product.

Uses of 3-Bromobenzoic acid: It can react with methanol to get 3-bromo-benzoic acid methyl ester. This reaction needs reagent HCl.

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, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)c1cc(Br)ccc1
2. InChI:InChI=1/C7H5BrO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H,9,10)
3. InChIKey:VOIZNVUXCQLQHS-UHFFFAOYAC