141336-51-8

Basic information

• Product Name: Cyclobutanecarbonitrile, 1-(phenylmethyl)-
• CAS NO: 141336-51-8
• Molecular Formula: C12H13N
• Molecular Weight: 171.242
• Mol File: 141336-51-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Cyclobutanecarbonitrile, 1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclobutanecarbonitrile, 1-(phenylmethyl)-(141336-51-8)
• EPA Substance Registry System: Cyclobutanecarbonitrile, 1-(phenylmethyl)-(141336-51-8)

Safety Data

• Hazardous Substances Data: 141336-51-8(Hazardous Substances Data)

Upstream product

• 109-64-8 1,3-dibromo-propane 
• 100-44-7 benzyl chloride 
• 108-18-9 diisopropylamine 
• 101329-85-5 1-(phenylthio)cyclobutanecarbonitrile 
• 100-39-0 benzyl bromide 
• 4426-11-3 cyclobutanecarbonitrile 
• 1360557-41-0 1-(phenylsulfinyl)cyclobutanecarbonitrile 

Downstream Products

• 141336-52-9 [1-[(Phenyl)methyl]cyclobutyl]methanamine 
• 114672-02-5 1-benzylcyclobutane-1-carboxylic acid 

Relevant articles and documents

Arylthio-metal exchange of α-arylthioalkanenitriles

The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me 2CuLi to α-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.

Nitrile alkylations through sulfinyl-metal exchange

Triple alkylation: Phenylsulfinyl- and phenylthioacetonitrile can function as trianion equivalents of acetonitrile by sequential alkylation and sulfinyl-metal exchange (see scheme; mCPBA=meta-chloroperoxybenzoic acid). The metalated nitriles alkylate a range of electrophiles to obtain nitriles with quaternary centers. The sulfinyl-metal exchange proceeds under very mild conditions and has a high functional-group tolerance. Copyright