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88-65-3

Basic Information
CAS No.: 88-65-3
Name: 2-Bromobenzoic acid
Article Data: 146
Molecular Structure:
Molecular Structure of 88-65-3 (2-Bromobenzoic acid)
Formula: C7H5BrO2
Molecular Weight: 201.019
Synonyms: Benzoic acid, o-bromo-;Benzoic acid, 2-bromo-;o-Bromobenzoic acid;2-Bromobenzoate;o-Bromobenzoicacid;
EINECS: 201-848-6
Density: 1.701 g/cm3
Melting Point: 146-151 °C
Boiling Point: 296.4 °C at 760 mmHg
Flash Point: 133.1 °C
Solubility: slightly soluble in water
Appearance: White to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38-36-37/38
Safety: 26-36-24/25-37/39
PSA: 37.30000
LogP: 2.14730
Synthetic route
610-94-6

2-bromobenzoic acid methyl ester

88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 10 - 20℃; for 1.08333h;100%
With iodine; aluminium In acetonitrile at 80℃; for 18h;99%
23975-63-5

1-(2-bromophenyl)-4,4,4-trifluorobutane-1,3-dione

88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation;96%
95-46-5

2-methylphenyl bromide

88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h;95%
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h; Rate constant; pH 9;95%
With potassium acetate In water93.2%
6630-33-7

ortho-bromobenzaldehyde

88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
With oxygen; Langlois reagent In acetonitrile at 25℃; under 760.051 Torr; for 12h; Irradiation; Green chemistry;95%
With tert.-butylhydroperoxide; potassium tert-butylate In water at 60℃; for 5h;90%
With oxygen at 120℃; for 5h; Neat (no solvent);85%
18982-54-2

o-bromobenzyl alcohol

88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
With sodium bromate; sodium hydrogen sulfate In acetonitrile for 20h; Heating;95%
With Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;91%
With 3,5-Lutidine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; sodium persulfate; tris(2,2'‐bipyridine)ruthenium(II) hexafluorophosphate In water; acetonitrile at 20℃; for 48h; Sealed tube; Irradiation;75%
2039-88-5

2-bromostyrene

88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
Stage #1: 2-bromostyrene With tert.-butylhydroperoxide; iron(III) chloride hexahydrate; sodium hydroxide In water at 80℃; for 10h;
Stage #2: With hydrogenchloride In water at 20℃;
95%
With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile for 24h;81%
With Oxone In water; acetonitrile for 24h; Reflux;77%

1-(2-bromophenyl)-1,2-ethanediol

88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; potassium tert-butylate In water at 80℃; for 8h;94%
95-46-5

2-methylphenyl bromide

88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
With potassium bromide; potassium acetate92.7%

2-(2-bromophenyl)-2-oxoacetaldehyde

88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
With iodine; dimethyl sulfoxide at 180℃; for 0.0833333h; Inert atmosphere; Microwave irradiation;92%

C12H13BrOS2

88-65-3

2-bromobenzoic-acid

Conditions
ConditionsYield
With sodium hydroxide In water at 100℃; for 9h; Reflux; chemoselective reaction;92%
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    Name 2-Bromobenzoic acid Molecular Structure Molecular Formula C7H5BrO2 Molecular Weight 2

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of this chemical is 2-bromobenzoic acid. With the CAS registry number 88-65-3, it is also named as Benzoic acid, 2-bromo-. The product's categories are Aromatic Compounds; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Benzoic Acid; Organic Acids; Acids & Esters; Bromine Compounds; C7; Carbonyl Compounds; Carboxylic Acids. It is white to light yellow crystal powder which is soluble in alcohol, ether, acetone, chloroform and hot water, slightly soluble in cold water. When heated to decomposition it emits toxic vapors of Br. Additionally, this chemical should be sealed in the container.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.15; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.38; (4)ACD/LogD (pH 7.4): -0.98; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.04; (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: 56.62 kJ/mol; (18)Vapour Pressure: 0.000649 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 2-Bromobenzoic acid: It can be obtained by 1-bromo-2-methyl-benzene. This reaction should react at 350 °C.

Uses of 2-Bromobenzoic acid: It is used in organic synthesis. For example: it can react with 1-(4-amino-phenyl)-ethanone to get N-(4-acetyl-phenyl)-anthranilic acid. This reaction needs reagent potassium carbonate, copper(I) chloride, catalytic agent copper powder and solvent dimethylformamide at temperature of 140-145 °C. The reaction time is 6 hours. The yield is 76%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin, so people should avoid contact with skin and eyes. 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)c1ccccc1Br
2. InChI:InChI=1/C7H5BrO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
3. InChIKey:XRXMNWGCKISMOH-UHFFFAOYAG

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD oral > 500mg/kg (500mg/kg)   National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 7, 1953.