1187-46-8

Basic information

• Product Name: ethyl 2-bromo-2-cyano-acetate
• Synonyms: ethyl 2-bromo-2-cyano-acetate;Bromocyanoacetic acid ethyl ester;Acetic acid, 2-broMo-2-cyano-, ethyl ester;Ethyl-alpha-broMo-alpha-cyanoacetate
• CAS NO: 1187-46-8
• Molecular Formula: C₅H₆BrNO₂
• Molecular Weight: 192.03
• Mol File: 1187-46-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 208.6°C at 760 mmHg
• Flash Point: 79.9°C
• Appearance: /
• Density: 1.6662 (rough estimate)
• Vapor Pressure: 0.212mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: ethyl 2-bromo-2-cyano-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-bromo-2-cyano-acetate(1187-46-8)
• EPA Substance Registry System: ethyl 2-bromo-2-cyano-acetate(1187-46-8)

Safety Data

• Hazardous Substances Data: 1187-46-8(Hazardous Substances Data)

Usage

General Description

Ethyl 2-bromo-2-cyano-acetate is a chemical compound with the molecular formula C6H7BrO2N. It is a colorless liquid with a fruity odor and is commonly used in organic synthesis as a reagent for the preparation of various pharmaceutical and agrochemical compounds. The compound is known for its versatile reactivity, particularly in the formation of carbon-carbon and carbon-nitrogen bonds. It is also used as a key intermediate in the synthesis of active pharmaceutical ingredients, making it of great interest to the pharmaceutical industry. However, it is important to handle ethyl 2-bromo-2-cyano-acetate with caution as it is considered harmful if swallowed, inhaled, or absorbed through the skin, and it may cause skin and eye irritation upon contact.

InChI:InChI=1/C5H6BrNO2/c1-2-9-5(8)4(6)3-7/h4H,2H2,1H3

Upstream product

• 18852-51-2 sodium cyanoacetic acid ethyl ester 
• 13280-85-8 ethyl 2,2-dibromo-2-cyanoacetate 
• 134890-52-1 ethyl 2-cyano-3-(4-methylphenyl)oxirane-2-carboxylate 
• 35768-29-7 ethyl 3-(4-chlorophenyl)-2-cyanooxirane-2-carboxylate 
• 292638-85-8 acrylic acid methyl ester 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 2169-68-8 ethyl (E)-3-(4-chlorophenyl)-2-cyanoacrylate 
• 127136-62-3 ethyl 2-cyano-5-phenylpenta-2,4-dienoate 
• 512785-45-4 4-amino-5-cyano-6-oxo-1-phenyl-3-carbohydrazido-N-(5-cyano-3-phenyl-4-hydroxythiazolidin-2-ylideno)pyridazine 
• 1391013-23-2 4-amino-2-benzoylimino-3-phenyl-2,3-dihydro-thiazole-5-carboxylic acid ester 
• 23998-32-5 4-(2-chloro-acetylamino)-3-(3-chloro-phenyl)-2-imino-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 23998-31-4 4-(2-chloro-acetylamino)-2-imino-3-p-tolyl-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 23998-34-7 4-(2-chloro-acetylamino)-2-imino-3-o-tolyl-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 24231-81-0 4-(2-chloro-acetylamino)-2-imino-3-phenyl-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 23998-10-9 4-(4-bromo-phenyl)-3'-(2-chloro-phenyl)-2,2'-diimino-2',3'-dihydro-[3,4']bithiazolyl-5'-carboxylic acid ethyl ester 
• 23998-09-6 4-(4-chloro-phenyl)-3'-(2-chloro-phenyl)-2,2'-diimino-2',3'-dihydro-[3,4']bithiazolyl-5'-carboxylic acid ethyl ester 
• 23998-05-2 3'-(4-ethoxy-phenyl)-2,2'-diimino-4-p-tolyl-2',3'-dihydro-[3,4']bithiazolyl-5'-carboxylic acid ethyl ester 
• 23998-07-4 4-(4-chloro-phenyl)-2,2'-diimino-3'-o-tolyl-2',3'-dihydro-[3,4']bithiazolyl-5'-carboxylic acid ethyl ester 
• 23998-11-0 4-(4-bromo-phenyl)-2,2'-diimino-3'-o-tolyl-2',3'-dihydro-[3,4']bithiazolyl-5'-carboxylic acid ethyl ester 
• 23998-03-0 3'-(2-chloro-phenyl)-2,2'-diimino-4-p-tolyl-2',3'-dihydro-[3,4']bithiazolyl-5'-carboxylic acid ethyl ester 

Relevant articles and documents

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Alkyl Halides via Visible Light Mediated Dehalogenation

Net selective bromination and chlorination of activated C-H bonds can be effected in generally high yield via a simple perhalogenation/dehalogenation sequence. The photochemical reductions require no photocatalyst, relying instead on the formation of an electron donor-acceptor complex of the substrate and reductant, or alternatively autophotocatalysis. Some reactions proceed despite any apparent photon absorption, serving as a cautionary tale for other photochemical reactions involving amines. Mechanistic experiments provide an explanation for this observation.

Tetrameric DABCO-bromine: An efficient and versatile reagent for bromination of various organic compounds

Tetrameric DABCO-bromine is a powerful brominating agent but shows reasonable selectivity with certain substrates. The selective bromination for activated aromatic compounds and alkenes is reported. Synthesis of α-bromo ketones and nitriles has also been achieved by using this reagent and the results are also reported. All products reported were obtained in good to excellent yields.