31253-11-9

Basic information

• Product Name: methyl 2-bromo-2-cyano-acetate
• Synonyms: methyl 2-bromo-2-cyano-acetate
• CAS NO: 31253-11-9
• Molecular Formula: C₄H₄BrNO₂
• Molecular Weight: 177.98
• Mol File: 31253-11-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 189.9°C at 760 mmHg
• Flash Point: 68.6°C
• Appearance: /
• Density: 1.695g/cm³
• Vapor Pressure: 0.558mmHg at 25°C
• Refractive Index: 1.482
• CAS DataBase Reference: methyl 2-bromo-2-cyano-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-bromo-2-cyano-acetate(31253-11-9)
• EPA Substance Registry System: methyl 2-bromo-2-cyano-acetate(31253-11-9)

Safety Data

• Hazardous Substances Data: 31253-11-9(Hazardous Substances Data)

Usage

General Description

Methyl 2-bromo-2-cyano-acetate is a chemical compound with the formula C5H6BrNO2. It is a colorless liquid with a strong odor, and it is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also used as a building block in organic synthesis, particularly in the production of fine chemicals and pharmaceuticals. Methyl 2-bromo-2-cyano-acetate is highly reactive and can undergo various chemical reactions, including esterification, hydrolysis, and substitution, which makes it a versatile compound in the field of organic synthesis. However, it is also important to handle this compound with caution, as it can be toxic and hazardous if not properly managed.

InChI:InChI=1/C4H4BrNO2/c1-8-4(7)3(5)2-6/h3H,1H3

Upstream product

• 15732-02-2 1-cyano-2,2-bis(methoxy)ethylene 
• 857576-02-4 2-bromo-3,3-dimethoxy-acrylonitrile 
• 64-19-7 acetic acid 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 67-66-3 chloroform 
• 105-34-0 methyl 2-cyanoacetate 

Downstream Products

• 35234-87-8 dimethyl 2,3-dicyanofumarate 
• 86814-28-0 3,5-bis(4-nitrophenyl)-1,2,4-thiadiazole 
• 1334212-42-8 3,5-bis(3-iodophenyl)-1,2,4-thiadiazole 
• 1334212-44-0 3,5-bis(2,3-dichlorophenyl)-1,2,4-thiadiazole 
• 1334212-40-6 3,5-bis(2-iodophenyl)-1,2,4-thiadiazole 
• 4115-17-7 3,5-bis-(4-chloro-phenyl)-[1,2,4]thiadiazole 
• 1334212-49-5 4,4'-(1,2,4-thiadiazole-3,5-diyl)dibenzonitrile 
• 1334212-43-9 3,5-bis(3-fluorophenyl)-1,2,4-thiadiazole 
• 1334212-48-4 3,5-bis(3,4-dichlorophenyl)-1,2,4-thiadiazole 
• 1334212-50-8 3,5-bis(4-(tert-butyl)phenyl)-1,2,4-thiadiazole 
• 1334212-47-3 3,5-bis(5-chloro-2-methylphenyl)-1,2,4-thiadiazole 
• 1334212-46-2 3,5-bis(2-bromo-4-methylphenyl)-1,2,4-thiadiazole 
• 1334212-45-1 3,5-bis(2,5-dichlorophenyl)-1,2,4-thiadiazole 
• 1334212-51-9 3,5-bis(4-butylphenyl)-1,2,4-thiadiazole 

Relevant articles and documents

Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets

Chemoprevention is an approach to decrease cancer morbidity and mortality through inhibition of carcinogenesis and prevention of disease progression. Although the trans stilbene derivative resveratrol has chemopreventive properties, its action is compromised by weak non-specific effects on many biological targets. Replacement of the stilbene ethylenic bridge of resveratrol with a 1,2,4-thiadiazole heterocycle and modification of the substituents on the two aromatic rings afforded potential chemopreventive agents with enhanced potencies and selectivities when evaluated as inhibitors of aromatase and NF-κB and inducers of quinone reductase 1 (QR1).

Bromination by means of sodium monobromoisocyanurate (SMBI)

A variety of aromatic compounds with both activating and deactivating substituents were brominated with sodium monobromoisocyanurate (SMBI) 1, diethyl ether, diethyl ether-methanesulfonic acid, trifluoroacetic acid, or sulfuric acid were employed as solvents. Thus nitrobenzene was conveniently brominated in sulfuric acid, benzene was readily monobrominated in diethyl ether-methanesulfonic acid, and phenol was selectively brominated at the ortho position under mild conditions in refluxing diethyl ether. With substituents that are easily protonated, trifluoroacetic acid may be employed as solvent in the reaction with 1, in contrast NBS was ineffective in trifluoroacetic acid. This renders 1 a superior reagent relative to NBS. In addition to aromatics, alkenes, ketones and esters were also brominated with 1. Diethyl malonate was brominated with 1 and then subjected to a Bingel reaction with NaH to afford the desired methanofullerene in reasonable yield.