125847-92-9

Basic information

• Product Name: benzyl 3-cyanopropanoate
• Synonyms: benzyl 3-cyanopropanoate
• CAS NO: 125847-92-9
• Molecular Weight: 189.214
• Mol File: 125847-92-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: benzyl 3-cyanopropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 3-cyanopropanoate(125847-92-9)
• EPA Substance Registry System: benzyl 3-cyanopropanoate(125847-92-9)

Safety Data

• Hazardous Substances Data: 125847-92-9(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 107-13-1 acrylonitrile 
• 100-51-6 benzyl alcohol 
• 292638-85-8 acrylic acid methyl ester 
• 40230-91-9 [(2-methoxyphenyl)ethynyl]trimethylsilane 
• 1624363-23-0 3-azido-2-methylbut-3-en-2-ol 
• 5437-45-6 Benzyl bromoacetate 
• 638-32-4 succinamic acid 

Relevant articles and documents

Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

Radical cyanomethylation via vinyl azide cascade-fragmentation

Herein, a novel methodology for radical cyanomethylation is described. The process is initiated by radical addition to the vinyl azide reagent 3-azido-2-methylbut-3-en-2-ol which triggers a cascade-fragmentation mechanism driven by the loss of dinitrogen and the stabilised 2-hydroxypropyl radical, ultimately effecting cyanomethylation. Cyanomethyl groups can be efficiently introduced into a range of substrates via trapping of α-carbonyl, heterobenzylic, alkyl, sulfonyl and aryl radicals, generated from a variety of functional groups under both photoredox catalysis and non-catalytic conditions. The value of this approach is exemplified by the late-stage cyanomethylation of pharmaceuticals.

Cobalt Carbonyl Mediated Michael Addition: Direct Synthesis of Esters Containing Other Functional Groups from Activated Olefins

Hydrocarbalkoxylation of acrylonitrile with stoichiometric amounts of alcohols in the presence of catalytic amounts of Co2(CO)8 and pyridine bases leads to 2,4-dicyano-2-methylbutanoic acid esters.The yield of these Michael adducts shows a maximum as a function of the pyridine/cobalt ratio.Analogues reactions using equimolar amounts of alcohol, acrylonitrile, and an other activated olefin result in products with at least three different functional groups.Acrylonitrile with pyH gives (1-cyanoethyl)cobalt tetracarbonyl, which is proposed to be the key intermediate of the hydrocarbalkoxylation.This complex may be deprotonated to a "Michael donor" anion, i.e. the Michael adducts are most probably formed in a cobalt-mediated way.The above catalytic system promoted also the Michael addition of some C-H acids to activated olefins under atmospheric conditions.