130457-35-1

Basic information

• Product Name: Carbamic acid, (1-cyano-2-methylpropyl)-, 1,1-dimethylethyl ester (9CI)
• Synonyms: tert-butyl 1-cyano-2-methylpropylcarbamate;Tert-Butyl N-(1-Cyano-2-Methylpropyl)Carbamate;Tert-Butyl N-(1-Cyano-2-Methylpropyl)Carbamate(WXC03918)
• CAS NO: 130457-35-1
• Molecular Formula: C10H18N2O2
• Molecular Weight: 198.26
• Product Categories: N-BOC
• Mol File: 130457-35-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, (1-cyano-2-methylpropyl)-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (1-cyano-2-methylpropyl)-, 1,1-dimethylethyl ester (9CI)(130457-35-1)
• EPA Substance Registry System: Carbamic acid, (1-cyano-2-methylpropyl)-, 1,1-dimethylethyl ester (9CI)(130457-35-1)

Safety Data

• Hazardous Substances Data: 130457-35-1(Hazardous Substances Data)

Upstream product

• 130457-26-0 t-butyl  
• 151-50-8 potassium cyanide 
• 4248-19-5 tert-butyl carbazate 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 365441-87-8 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methylpropanoic acid 
• 13734-41-3 N-Boc-(S/R)-valine 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 

Relevant articles and documents

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation

The one-step conversion of aliphatic carboxylic acids to the corresponding nitriles has been accomplished via the merger of visible light mediated photoredox and cyanobenziodoxolones (CBX) reagents. The reaction proceeded in high yields with natural and non-natural α-amino and α-oxy acids, affording a broad scope of nitriles with excellent tolerance of the substituents in the α position. The direct cyanation of dipeptides and drug precursors was also achieved. The mechanism of the decarboxylative cyanation was investigated both computationally and experimentally and compared with the previously developed alkynylation reaction. Alkynylation was found to favor direct radical addition, whereas further oxidation by CBX to a carbocation and cyanide addition appeared more favorable for cyanation. A concerted mechanism is proposed for the reaction of radicals with EBX reagents, in contrast to the usually assumed addition elimination process.

Photoinduced direct cyanation of C(sp3)-H bonds

A general and practical synthetic protocol for the direct transformation of unreactive C(sp3)-H bonds to C(sp3)-CN bonds has been developed. The homolytic cleavage of the C-H bond is initiated by photo-excited benzophenone, and the resulting carbon radical subsequently reacts with tosyl cyanide to afford the corresponding nitrile in a highly efficient manner. The present methodology is widely applicable to various starting materials including ethers, alcohols, amine derivatives, alkanes, and alkylbenzenes. This newly developed C-H cyanation protocol provides a powerful tool for selective one-carbon elongation for the construction of architecturally complex molecules. Georg Thieme Verlag Stuttgart - New York.

A convenient synthesis of N-boc-protected α-aminonitriles from α-amidosulfones

Synthesis of N-Boc-protected α-aminonitriles starting from N-Boc-protected α-aminosulfones is described. Treatment of the sulfone with two equivalents of potassium cyanide in 2-propanol or dichloromethane- H2O under phase transfer condition affords crystalline N-Boc-protected α-aminonitriles in good yield. Hydrolysis of the aminonitriles provides a convenient access to racemic α-amino acids.