3-Bromopyruvic acid

Base Information

• Chemical Name: 3-Bromopyruvic acid
• CAS No.: 1113-59-3
• Molecular Formula: C3H3BrO3
• Molecular Weight: 166.959
• Hs Code.: 2918.30
• European Community (EC) Number: 214-206-5
• NSC Number: 62343,11731
• UNII: 63JMV04GRK
• DSSTox Substance ID: DTXSID7040940
• Nikkaji Number: J138.327B
• Wikipedia: Bromopyruvic_acid
• Wikidata: Q3608257
• Metabolomics Workbench ID: 71558
• ChEMBL ID: CHEMBL177837
• Mol file: 1113-59-3.mol

Synonyms:3-bromopyruvate;3-bromopyruvic acid;bromopyruvate

Chemical Property of 3-Bromopyruvic acid

Chemical Property:

• Appearance/Colour: white to pale yellow crystalline powder
• Vapor Pressure: 0.0357mmHg at 25°C
• Melting Point: 77-82 °C
• Refractive Index: 1.521
• Boiling Point: 223.4 °C at 760 mmHg
• PKA: 1.84±0.54(Predicted)
• Flash Point: 88.9 °C
• PSA: 54.37000
• Density: 2.011 g/cm³
• LogP: 0.03500
• Storage Temp.: 2-8°C
• Solubility.: water: soluble1g/10 mL, clear, colorless
• Water Solubility.: Soluble in water, dimethyl sulfoxide, ethyl acetate and water.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 165.92656
• Heavy Atom Count: 7
• Complexity: 98.4

Purity/Quality:

99% ^*data from raw suppliers

Bromopyruvic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-20/21/22
• Safety Statements: 26-36/37/39-45-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(=O)C(=O)O)Br
• Uses: 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 aggress ive liver tumors. Bromopyruvic acid is used as an affinity label for cysteine residues and a potential anti-cancer agent. It is involved in the synthesis of imidazo[1,2-a]pyridine-2-carboxylic acids and substituted pyranones. It plays a vital role as a cross-linker between nucleic acids and proteins. It is used as an anticancer agent for lung tumors. 3-Bromopyruvic acid is an intermediate of the fungicide thiabendazole. It was also used in the synthesis of imidazo[1,2-a]pyridine-2-carboxylic acids.

Technology Process of 3-Bromopyruvic acid

There total 7 articles about 3-Bromopyruvic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

→ bromopyruvic acid (1113-59-3)

Guidance literature:

Reference yield: 90.0%

2-oxo-propionic acid (127-17-3) → bromopyruvic acid (1113-59-3)

Guidance literature:

With sulfuric acid; bromine; for 1h;

DOI:10.1021/jo00140a036

Reference yield:

ethyl diazopyruvate (14214-10-9) → bromopyruvic acid (1113-59-3) + ethyl Bromopyruvate (70-23-5)

Guidance literature:

With diethyl ether; hydrogen bromide;

upstream raw materials:

ethyl diazopyruvate

2-oxo-propionic acid

acetylacetone

water

Downstream raw materials:

3-hydroxy-6-methoxy-quinoline-4-carboxylic acid

6-bromo-3-hydroxyquinoline-4-carboxylic acid

2-phenyl-1,3-oxazole-4-carboxylic acid

2-aminothiazole-4-carboxylate

Refernces

• 1、 -. "METHODS OF SYNTHESIS AND USE OF CHEMOSPHERES". . . Retrieved 2011/05/08.
• 2、 Frutos, Rogelio P.,Haddad, Nizar,Houpis, Ioannis N.,Johnson, Michael,Smith-Keenan, Lana L.,Fuchs, Victor,Yee, Nathan K.,Farina, Vittorio,Faucher, Anne-Marie,Brochu, Christian,Hache, Bruno,Duceppe, Jean-Simon,Beaulieu, Pierre. "Practical synthesis of 2-(2-isopropylaminothiazol-4-yl)-7-methoxy-1H- quinolin-4-one: Key intermediate for the synthesis of potent HCV NS3 protease inhibitor BILN 2061". . p. 2563 - 2567. Retrieved 2008/02/04.