2-bromobenzoic acid

• ChemBase ID: 89431
• Molecular Formular: C7H5BrO2
• Molecular Mass: 201.0174
• Monoisotopic Mass: 199.9472914
• SMILES: OC(=O)c1c(cccc1)Br
• Canonical SMILES: OC(=O)c1ccccc1Br
• InChI: InChI=1S/C7H5BrO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
• InChIKey: XRXMNWGCKISMOH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromobenzoic acid
• IUPAC Traditional name: O-bromobenzoic acid
• Synonyms: 2-Bromobenzoic acid 97%; 2-Bromobenzoic acid; 2-Bromobenzoic acid; 2-Bromobenzoic acid; o-BROMOBENZOIC ACID; 2-溴苯甲酸

Database IDs

• CAS Number: 88-65-3
• EC Number: 201-848-6
• MDL Number: MFCD00002402
• Beilstein Number: 971266
• PubChem SID: 162076311; 24850027; 24848342
• PubChem CID: 6940

CALCULATED PROPERTIES

• Acid pKa: 3.2514994
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.17080286
• LogD (pH = 7.4): -1.036349
• Log P: 2.3995814
• Molar Refractivity: 40.937 cm^3
• Polarizability: 15.599813 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 146-150°C; 146-150°C; 147-150 °C(lit.)
• Density: 1.930
• Vapor Pressure: >1 mmHg ( 20 °C)

Safety Information

• Storage Condition: 0°C
• Storage Warning: Irritant/Light Sensitive
• RTECS: DG4448035
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 36/37/38; R:36/37/38
• Safety Statements: 26-36; 26-37; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (HPLC); 97%; 98%
• Grade: purum
• Linear Formula: BrC6H4CO2H

DETAILS

MP Biomedicals - 02154865

(2-Bromobenzoic acid) Crystalline

Sigma Aldrich - 137677

Packaging
25, 100 g in poly bottle

REFERENCES

• Forms a dimetallated derivative with n-BuLi, which reacts with electrophiles preferentially at the ortho-carbon: J. Org. Chem., 39, 2051, 2053 (1974); e.g. with aroyl halides leads to 2-carboxybenzophenones which can be cyclized by acid to substituted anthraquinones: J. Org. Chem., 46, 1057 (1981).
• The Br can be displaced by malonate-type carbanions, in the presence of Cu catalysts: Angew. Chem. Int. Ed., 13, 340 (1974). For coupling with Na 2,4-pentanedionate, see: Org. Synth. Coll., 6, 36 (1988).