19521-13-2

Basic information

• Product Name: α,β-dibromo-β-phenylpropionitrile
• Synonyms: α,β-dibromo-β-phenylpropionitrile
• CAS NO: 19521-13-2
• Molecular Weight: 288.969
• Mol File: 19521-13-2.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: α,β-dibromo-β-phenylpropionitrile(CAS DataBase Reference)
• NIST Chemistry Reference: α,β-dibromo-β-phenylpropionitrile(19521-13-2)
• EPA Substance Registry System: α,β-dibromo-β-phenylpropionitrile(19521-13-2)

Safety Data

• Hazardous Substances Data: 19521-13-2(Hazardous Substances Data)

Upstream product

• 4360-47-8 cinnamonitrile 
• 1885-38-7 cinnamic nitrile 
• 621-79-4 cinnamamide 
• 66913-75-5 2-cyano-3-phenylaziridine 

Downstream Products

• 85485-60-5 1-methyl-5-phenyl-1H-pyrazol-3-amine 
• 4360-47-8 cinnamonitrile 
• 1079850-26-2 1,2-dimethylindazolium bromide 
• 1092776-44-7 3-bromo-1,2-dimethylindazolium bromide 
• 19522-37-3 (E)-1-bromo-1-cyano-2-phenylethene 
• 91164-91-9 3-((Z)-2-Cyano-1-phenyl-vinyl)-1-methyl-3H-imidazol-1-ium; iodide 
• 88218-84-2 phenyl-3-thiophenyl-3-propenonitrile 
• 54232-30-3 3-phenyl-3-pyrrolidin-1-yl-acrylonitrile 
• 93173-73-0 (Z)-3-Ethylsulfanyl-3-phenyl-acrylonitrile 
• 77643-62-0 1-Cyclohexyl-2,4-diphenyl-1H-pyrrole-3-carbonitrile 
• 77643-64-2 1-Benzyl-2,4-diphenyl-1H-pyrrole-3-carbonitrile 
• 77643-59-5 (Z)-3-tert-Butylamino-3-phenyl-acrylonitrile 
• 77643-58-4 3-(N-Isopropyl)amino-3-phenylpropanenitrile 
• 35303-22-1 erythro-1-benzyl-2-cyano-3-phenylaziridine 

Relevant articles and documents

Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes

Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is

NOVEL COMPOUNDS

The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase L1 (UCHL1). The invention further relates to the use of DUB inhibitors in the treatment of cancer and other indications. Compounds of the invention include compounds having the formula (I) or a pharmaceutically acceptable salt thereof, wherein R1 to R8 are as defined herein.

The synthesis of alkyl aryl nitriles from N-(1-arylalkylidene)-cyanomethylamines. Part 2. Mechanism

The mechanism of the rearrangement of N-(1-arylalkylidene)cyanomethylamines ArC(=NCH2CN)R 1 to the corresponding nitriles ArCH(CN)R2 (in DMF, at 150°C, with K2CO3) is described. Reaction 1 → 2 was investigated for different types of imine 1, and it was found that with a leaving group other than CN- the reaction does not proceed to yield the nitrile, whereas imines such as PhC(=NCH2CN)H, prepared starting from aldehydes rather than ketones, yield the expected phenylacetonitrile even at temperatures as low as 120°C. Evidence for the mechanism comes from a study of the reactivity of the postulated intermediates: 2-cyano-3-phenylaziridine 4c, and 2,2-diphenyl-2H-azirine 5b. The route involving aziridine 4c is ruled out, since this compound does not react at all under the investigated conditions. The 2H-azirine 5b instead, yields the corresponding diphenylacetonitrile in DMF with K2CO3, at 150°C. The transformation seems to involve an initial deprotonation, followed by an intramolecular ring closure-CN elimination step, which yields the 2H-azirine. The azirine then isomerizes to the nitrile. Additional evidence for the intermediacy of the 2H-azirine, based on 1H NMR monitoring of the reaction 1 → 2, is described. Finally, the results of a simple isotope exchange experiment provide a rationale for the previously observed scrambling of labels, and further confirm the proposed mechanism.