34097-57-9

Basic information

• Product Name: (±)-2-(benzyloxy)propanenitrile
• Synonyms: (±)-2-(benzyloxy)propanenitrile
• CAS NO: 34097-57-9
• Molecular Weight: 161.203
• Mol File: 34097-57-9.mol

Chemical Properties

• CAS DataBase Reference: (±)-2-(benzyloxy)propanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-2-(benzyloxy)propanenitrile(34097-57-9)
• EPA Substance Registry System: (±)-2-(benzyloxy)propanenitrile(34097-57-9)

Safety Data

• Hazardous Substances Data: 34097-57-9(Hazardous Substances Data)

Upstream product

• 66183-20-8 2-benzyloxy-propionamide 
• 22821-76-7 4-(methylsulfonyl)benzonitrile 
• 100836-85-9 (R)-2-benzyloxypropionic acid 
• 33106-32-0 2-(benzyloxy)propanoic acid 
• 172876-96-9 3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 935-04-6 benzyl vinyl ether 
• 78-97-7 2-hydroxy-propionitrile 
• 100-51-6 benzyl alcohol 

Relevant articles and documents

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.

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.

Decarboxylative alkynylation and cyanation of carboxylic acids using photoredox catalysis and hypervalent iodine reagents

Alkynes and nitriles are important functional groups that serve as versatile building blocks in organic synthesis and find applications in material and medicinal sciences. A convenient and straightforward access to both classes of compounds under mild conditions is, therefore, highly desirable. Herein, we disclose the decarb-oxylative alkynylation and cyanation of broadly available carboxylic acids using photoredox catalysis and hyper-valent iodine reagents. Choices of both catalysts and reagents were crucial. Computational and experimental studies revealed two different possible mechanisms that are dictated by the oxidation potential of the reagents: radical for alkynylation, ionic for cyanation.

Stereocontrolled cyanohydrin ether synthesis through chiral Bronsted acid-mediated vinyl ether hydrocyanation

Vinyl ethers can be protonated to generate oxocarbenium ions that react with Me3SiCN to form cyanohydrin alkyl ethers. Reactions that form racemic products proceed efficiently upon conversion of the vinyl ether to an α-chloro ether prior to cya