59831-96-8

Basic information

• Product Name: N-cyclopropyl-3-phenylprop-2-enamide
• CAS NO: 59831-96-8
• Molecular Formula: C₁₂H₁₃NO
• Molecular Weight: 187.2377
• Mol File: 59831-96-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 396.3°C at 760 mmHg
• Flash Point: 235.7°C
• Density: 1.1g/cm³
• Vapor Pressure: 1.72E-06mmHg at 25°C
• Refractive Index: 1.579
• CAS DataBase Reference: N-cyclopropyl-3-phenylprop-2-enamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-cyclopropyl-3-phenylprop-2-enamide(59831-96-8)
• EPA Substance Registry System: N-cyclopropyl-3-phenylprop-2-enamide(59831-96-8)

Safety Data

• Hazardous Substances Data: 59831-96-8(Hazardous Substances Data)

Upstream product

• 1447254-55-8 N-cyclopropylcinnamimidoyl cyanide 
• 102-92-1 Cinnamoyl chloride 
• 765-30-0 Cyclopropylamine 
• 140-10-3 (E)-3-phenylacrylic acid 
• 66894-04-0 2,3-dibromo-3-phenyl propanal 
• 33603-90-6 (2Z)-2-bromo-3-phenyl-2-propenal 

Relevant articles and documents

1,3-Difunctionalization of Aminocyclopropanes via Dielectrophilic Intermediates

We report an oxidative ring-opening strategy to transform acyl, sulfonyl or carbamate protected aminocyclopropanes into 1,3-dielectrophilic carbon intermediates bearing a halide atom (Br, I) and a N,O-acetal. Replacing the alkoxy group of the N,O-acetal can be achieved under acidic conditions through an elimination–addition pathway, while substitution of the halides by nucleophiles can be done under basic conditions through a SN2 pathway, generating a wide range of 1,3-difunctionalized propylamines. A proof of concept for asymmetric induction was realized using a chiral phosphoric acid (CPA) as catalyst, highlighting the potential of the method in enantioselective synthesis of important building blocks.

Amidation of aldehydes and alcohols through α-iminonitriles and a sequential oxidative three-component strecker reaction/thio-michael addition/alumina-promoted hydrolysis process to access β-mercaptoamides from aldehydes, amines, and thiols

Mild and general alumina-promoted hydrolysis conditions for converting α-iminonitriles into carboxamides have been developed. In combination with the oxidative three-component Strecker reaction, the one-pot direct amidation of aldehydes and alcohols is reported. Subsequently, an Yb(OTf) 3-catalyzed Michael addition of thiols to α,β-unsaturated α-iminonitriles is reported for the synthesis of β-mercapto-α- iminonitriles. The successful integration of an oxidative Strecker reaction, thio-Michael addition, and neutral-alumina-promoted hydrolysis of β-mercapto-α-iminonitriles into a three-component one-pot process allowed us to develop the direct conversion of amines, aldehydes, and thiols into β-mercaptoamides. All of these procedures were applicable to aromatic and aliphatic amines and aldehydes. First direct: The direct amidation reactions of aldehydes and alcohols were performed in combination with the oxidative three-component synthesis of α-iminonitriles. In addition, β-mercaptoamides were readily accessed from α,β-unsaturated aldehydes, amines, and thiols by a sequential process that involved a three-component Strecker reaction, Yb(OTf)3-catalyzed thio-Michael addition, and hydrolysis of the resulting β-mercapto-α-iminonitriles (see scheme). Copyright