3-bromo-2-oxopropanoic acid

• ChemBase ID: 92281
• Molecular Formular: C3H3BrO3
• Molecular Mass: 166.95812
• Monoisotopic Mass: 165.92655596
• SMILES: BrCC(=O)C(=O)O
• Canonical SMILES: OC(=O)C(=O)CBr
• InChI: InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
• InChIKey: PRRZDZJYSJLDBS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-bromo-2-oxopropanoic acid
• IUPAC Traditional name: bromopyruvic acid
• Synonyms: 3-Bromo-2-oxopropanoic Acid; NSC 11731; NSC 62343; β-Bromopyruvic Acid; 3-Bromopyruvic acid; 3-Bromo-2-oxopropionic acid; 3-Bromo-2-oxopropanoic acid; Bromopyruvate; 3-Bromopyruvate; 3-BrPA; Bromopyruvic acid; Bromopyruvic acid; 3-溴-2-氧代丙酸; 溴丙酮酸

Database IDs

• CAS Number: 1113-59-3
• EC Number: 214-206-5
• MDL Number: MFCD00002587
• Beilstein Number: 1746786
• PubChem SID: 162078979; 24854297; 24850104
• PubChem CID: 70684
• CHEMBL: 177837
• Chemspider ID: 63850
• Wikipedia Title: Bromopyruvic_acid

CALCULATED PROPERTIES

• Acid pKa: 1.7912446
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.5205314
• LogD (pH = 7.4): -2.7371578
• Log P: 0.78871304
• Molar Refractivity: 25.7264 cm^3
• Polarizability: 10.159609 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 75-80°C; 75-82°C; 77 - 82°C; 77-82 °C; 79-82 °C (hydrate)
• Hydrophobicity(logP): -0.631

Safety Information

• Storage Warning: Corrosive/Lachrymatory/Light Sensitive/Air Sensitive/Moisture Sensitive/Store under Argon/Keep Cold
• RTECS: UZ0840000
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 34; R34
• Safety Statements: 26-36/37/39-45; S25 S36/37/39 S45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P280-P303+P361+P353-P305+P351+P338-P310; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97.0% (T); 95%; 97%; 98%
• Linear Formula: BrCH2COCOOH

DETAILS

Sigma Aldrich - 238341

Application
Substrate employed in the synthesis of substituted pyranones.1
Packaging
5 g in glass bottle

Sigma Aldrich - 16490

General description
may contain traces of dibromopyruvic acid
Other Notes
Affinity label for cysteine residues1,2; Cross-linker between nucleic acids and proteins3
Packaging
10, 50, 500 g in glass bottle

Toronto Research Chemicals - B686930

Bromopyruvic Acid is a synthetic brominated derivative of pyruvic acid. Bromopyruvic Acid maybe a potential treatment for certain types of cancer as it has shown to be effective at eliminating aggressive liver tumors.

REFERENCES

• Ko Y.H. et al.: Cancer Lett., 173, 83 (2001)
• Geschwind J.F. et al.: Cancer Res., 62, 3209 (2001)
• Ko Y.H. et al.: J. Bioenerg. Biomembr., 44, 163 (2001)