63909-24-0

Basic information

• Product Name: Benzenebutanenitrile, a-methylene-
• CAS NO: 63909-24-0
• Molecular Formula: C11H11N
• Molecular Weight: 157.215
• Mol File: 63909-24-0.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Benzenebutanenitrile, a-methylene-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenebutanenitrile, a-methylene-(63909-24-0)
• EPA Substance Registry System: Benzenebutanenitrile, a-methylene-(63909-24-0)

Safety Data

• Hazardous Substances Data: 63909-24-0(Hazardous Substances Data)

Upstream product

• 2408-36-8 lithium cyanide 
• 87837-53-4 (E)-[(4-phenylbut-1-en-1-yl)sulfonyl]benzene 
• 147297-67-4 S-<(E)-Non-1-enyl>-S-phenyl-N-(p-tolylsulfonyl)sulfoximine 
• 147297-66-3 (S)-(+)-(E)-S-phenyl-S-(4-phenylbut-1-enyl)-N-(p-tolylsulfonyl)sulfoximine 
• 557-21-1 zinc(II) cyanide 
• 16520-62-0 4-Phenyl-1-butyne 
• 14906-59-3 4-cyanopyridine N-oxide 
• 7677-24-9 trimethylsilyl cyanide 
• 768-56-9 4-Phenylbut-1-ene 
• 103-63-9 1-phenyl-2-bromoethane 
• 107-13-1 acrylonitrile 
• 104-53-0 3-phenyl-propionaldehyde 
• 80922-14-1 (E)-(4-nitrobut-3-enyl)benzene 
• 17200-53-2 α-(bromomethyl)acrylonitrile 

Downstream Products

• 136091-86-6 1,2-dicyano-4-phenylbutane 

Relevant articles and documents

Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer

We report nickel-catalyzed cyanation and hydrocyanation methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and nontoxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerances. In hydrocyanation of alkynes, the method demonstrated good regioselectivity, producing predominantly E- or Z-alkenyl nitriles in a controlled manner and exclusively Markovnikov vinyl nitriles when internal diaryl alkynes and terminal alkynes were applied as the substrates, respectively. The preliminary mechanistic investigation indicated that the C-CN bond cleavage process is promoted by oxidative addition to the nickel(I) complex in the cyanation of aryl halides, and further studies via a series of deuterium exchange experiments indicated that water serves as the hydrogen source for the hydrocyanation of alkynes.

Nickel-catalyzed regioselective hydrocyanation of terminal alkynes by assistance of a tosyl group

Nickel-catalyzed regioselective hydrocyanation of terminal alkynes is described. A tosylamide functionality at the propargyl position was the most suitable group for controlling the regiochemistry for C–CN bond formation as well as rate enhancement. A gram-scale synthesis was achieved by minimizing the catalyst loading to 2 mol%. The major HCN adduct could be transformed to the corresponding indoline through construction of a benzylic quaternary carbon under iron catalysis.

Nickel-Catalyzed Highly Regioselective Hydrocyanation of Terminal Alkynes with Zn(CN)2 Using Water as the Hydrogen Source

The first efficient and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)2 in the presence of water has been developed. The reaction provides a regioselective protocol for the synthesis of functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions while obviating use of the volatile and hazardous reagent of HCN. Deuterium-labeling experiments confirmed the role of water as the hydrogen source in this hydrocyanation reaction.