3-Bromopyruvic acid Property

Melting point:

77-82 °C

Boiling point:

223.4±23.0 °C(Predicted)

Density 

1.7314 (rough estimate)

refractive index 

1.4650 (estimate)

storage temp. 

2-8°C

solubility 

water: soluble1g/10 mL, clear, colorless

form 

White crystalline solid

pka

1.84±0.54(Predicted)

color 

White to Almost white

Water Solubility 

Soluble in water, dimethyl sulfoxide, ethyl acetate and water.

BRN 

1746786

InChIKey

PRRZDZJYSJLDBS-UHFFFAOYSA-N

CAS DataBase Reference

1113-59-3(CAS DataBase Reference)

EPA Substance Registry System

Propanoic acid, 3-bromo-2-oxo- (1113-59-3)

Safety

Hazard Codes 

C

Risk Statements 

34-20/21/22

Safety Statements 

26-36/37/39-45-27

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

RTECS 

UZ0840000

F 

19-21

Hazard Note 

Corrosive

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29183000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Bromopyruvic acid Chemical Properties,Usage,Production

Chemical Properties

Off-white solid

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.

Uses

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.

Uses

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.

Preparation

Synthesis 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.

Definition

ChEBI: 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.

General Description

Bromopyruvic 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.

storage

Store at -20°C

Purification Methods

Dry it by azeotropic distillation (with toluene), and then recrystallise it from dry CHCl3. Dry for 48hours at 20o (0.5 torr) over P2O5. Store it at 0o. [Labandiniere et al. J Org Chem 52 157 1987, Beilstein 3 III 1167.]