Basic information
- Standard SMILES
O=C(O)C(=O)CBr- InChIKey
PRRZDZJYSJLDBS-UHFFFAOYSA-N- Molecular formula
- C3H3BrO3
- Average molar mass
- 166.96 g/mol
- Monoisotopic mass
- 165.92655606
Overview
3-bromopyruvic acid is a 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is replaced by bromine. Synthetic brominated derivative and structural analog of pyruvic acid. Highly reactive alkylating agent. Anti-cancer drug. It has a role as an alkylating agent and an antineoplastic agent. It is a 2-oxo monocarboxylic acid and an organobromine compound. It is functionally related to a pyruvic acid. It is a conjugate acid of a 3-bromopyruvate.
Names & identifiers
- Preferred name
- Bromopyruvic Acid
- IUPAC
- 3-bromo-2-oxopropanoic acid
- English name
- 3-Bromopyruvic acid
- Molecular formula
- C3H3BrO3
- Molecular weight
- 166.96
Names & synonyms
bromopyruvic acid3-bromopyruvic acid1113-59-33-bromo-2-oxopropanoic acidbromopyruvate3-Bromo-2-oxopropionic acid63JMV04GRKDTXSID7040940NSC-11731NSC-62343CHEBI:1314613-BrPA cpd
Show more names
2-Oxo-3-bromopropanoic acidbeta-bromopyruvicacidNSC 11731NSC 62343
RefChem:499406DTXCID5020940214-206-53-bromopyruvatePyruvic acid, bromo-Propanoic acid, 3-bromo-2-oxo-3-bromopyruvicacidMFCD00002587
Database identifiers
- CAS
1113-59-3- PubChem CID
- 70684
- DTXSID
DTXSID7040940- ChEMBL
CHEMBL177837- ChEBI
CHEBI:131461- UNII
- 63JMV04GRK
- EC Number
- 214-206-5
- Nikkaji
- J138.327B
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 98.4
Physicochemical properties
- Melting point
- 77 · 77-82 °C
- Boiling point
- 223.4 · 223.4±23.0 °C(Predicted)
- Density
- 1.7314 · 1.7314 (rough estimate)
- refractive index
- 1.465 · 1.4650 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 1 g/10 · water: soluble1g/10 mL, clear, colorless
- form
- White crystalline solid
- pka
- 1.84 · 1.84±0.54(Predicted)
- color
- White to Almost white
- Water Solubility
- Soluble in water, dimethyl sulfoxide, ethyl acetate and water.
- BRN
- 1746786 · 1746786
- InChI
- InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)
- InChIKey
- PRRZDZJYSJLDBS-UHFFFAOYSA-N
- SMILES
- C(O)(=O)C(=O)CBr
- CAS DataBase Reference
- 1113 · 1113-59-3(CAS DataBase Reference)
- FDA UNII
- 63 JMV04GRK · 63JMV04GRK
- EPA Substance Registry System
- 3 · Propanoic acid, 3-bromo-2-oxo- (1113-59-3)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314
- Precautionary statements
- 260 · P260-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C
- Risk Statements
- 34 · 34-20/21/22
- Safety Statements
- 26 · 26-36/37/39-45-27
- RIDADR
- 3261 · UN 3261 8/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 840000 · UZ0840000
- F
- 19 · 19-21
- Hazard Note
- Corrosive
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29183000 · 29183000
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 Skin · Eye Dam. 1Skin Corr. 1B
Safety & regulation
GHS classification
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 6 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Corr. 1B (100%)
Safety data
- F
- 19-21
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UZ0840000
- ridadr
- UN 3261 8/PG 2
- hs_code
- 29183000
- risk_code
- 34-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C
- hazard_note
- Corrosive
- safety_code
- 26-36/37/39-45-27
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- H314
- Hazard Classifications
- Eye Dam. 1Skin Corr. 1B
- Precautionary statements
- P260-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Analogs of those substrates or compounds which bind naturally at the active sites of proteins, enzymes, antibodies, steroids, or physiological receptors. These analogs form a stable covalent bond at the binding site, thereby acting as inhibitors of the proteins or steroids.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Uses & manufacturing
General Manufacturing InformationPropanoic acid, 3-bromo-2-oxo-: ACTIVE
Applications
UsesBromopyruvic 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.
UsesBromopyruvic 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.
Uses3-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.
General DescriptionBromopyruvic acid is an affinity label for cysteine residues. It acts as cross-linker between nucleic acids and proteins. Kinetics of inactivation of pancreatic ribonuclease A by bromopyruvic acid has been investigated.
Preparation methods
PreparationSynthesis method of 3-bromopyruvic acid: add a little concentrated sulfuric acid and solvent dichloromethane to pyruvic acid in a reaction flask, add bromine dropwise for about 3.5h and stir, a white precipitate is produced, then continue to stir for 1h, dilute with cyclohexane and petroleum ether, then cool the reaction mixture to get crystals, filter, wash with petroleum ether and dry to get the finished product of 3-bromopyruvic acid.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: 3-bromopyruvic acid is a 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is replaced by bromine. Synthetic brominated derivative and structural analog of pyruvic acid. Highly reactive alkylating agent. Anti-cancer drug It has a role as an alkylating agent and an antineoplastic agent. It is a 2-oxo monocarboxylic acid and an organobromine compound. It derives from a pyruvic acid. It is a conjugate acid of a 3-bromopyruvate.
Related reactions
55 records
Linked notes
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