4-bromo-2-nitrobenzoic acid

• ChemBase ID: 12188
• Molecular Formular: C7H4BrNO4
• Molecular Mass: 246.01496
• Monoisotopic Mass: 244.93236961
• SMILES: c1c(cc(c(c1)C(=O)O)[N+](=O)[O-])Br
• Canonical SMILES: Brc1ccc(c(c1)[N+](=O)[O-])C(=O)O
• InChI: InChI=1S/C7H4BrNO4/c8-4-1-2-5(7(10)11)6(3-4)9(12)13/h1-3H,(H,10,11)
• InChIKey: ZIRHHEZLJGORGU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-bromo-2-nitrobenzoic acid
• IUPAC Traditional name: 4-bromo-2-nitrobenzoic acid
• Synonyms: 4-Bromo-2-nitrobenzoic acid; 4-Bromo-2-nitrobenzoic acid; 5-Bromo-2-carboxynitrobenzene; 4-溴-2-硝基苯甲酸

Database IDs

• CAS Number: 99277-71-1
• MDL Number: MFCD01013599
• PubChem SID: 24884696; 160975495
• PubChem CID: 3774467

CALCULATED PROPERTIES

• Acid pKa: 1.6352308
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.0249962
• LogD (pH = 7.4): -1.1873839
• Log P: 2.3395655
• Molar Refractivity: 47.2575 cm^3
• Polarizability: 17.742582 Å^3
• Polar Surface Area: 80.44 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 165-169; 165-169 °C; 165-169°C; 165-169°C
• Partition Coefficient: 2.351
• Hydrophobicity(logP): 2.365

Safety Information

• Storage Warning: Harmful; IRRITANT
• European Hazard Symbols: Nature polluting (N); Irritant (Xi); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-36/37/38-43-50; 36/37/38
• Safety Statements: 26-36/37-61; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H317-H319-H335-H400; H315-H319-H335
• GHS Precautionary statements: P261-P273-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Product Information

• Purity: 95%; 95+%; 97%; 98%
• Linear Formula: (Br)C6H3(NO2)CO2H

DETAILS

Sigma Aldrich - 664855

Application
Undergoes Negishi-type coupling with dimethylzinc in the presence of palladium-phosphine catalysis.1
Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - B686225

4-Bromo-2-nitrobenzoic acid is an intermediate in the synthesis of Lonafarnib (L469445), a potential anticancer agent.

REFERENCES

• Pellicani, R.Z., et al.: J. Med. Chem., 55, 424 (2012)