138145-57-0

Basic information

• Product Name: Pentanedinitrile, 3-(phenylmethoxy)-
• Synonyms: 3-(benzyloxy)glutaronitrile;3-O-(benzyl)-glutaronitrile;3-benzyloxypentanedinitrile;Pentanedinitrile,3-(phenylmethoxy)
• CAS NO: 138145-57-0
• Molecular Formula: C12H12N2O
• Molecular Weight: 200.23600
• Mol File: 138145-57-0.mol

Chemical Properties

• CAS DataBase Reference: Pentanedinitrile, 3-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanedinitrile, 3-(phenylmethoxy)-(138145-57-0)
• EPA Substance Registry System: Pentanedinitrile, 3-(phenylmethoxy)-(138145-57-0)

Safety Data

• Hazardous Substances Data: 138145-57-0(Hazardous Substances Data)

Upstream product

• 886433-28-9 oct-1-en-3-yn-2-ylbenzene 
• 7677-24-9 trimethylsilyl cyanide 
• 13880-89-2 3-hydroxyglutaronitrile 
• 100-39-0 benzyl bromide 

Downstream Products

• 138145-60-5 (S)-(+)-3-O-(benzyl)-4-cyanobutanoic acid 
• 476014-93-4 (S)-4-Benzyloxy-piperidin-2-one 
• 150966-87-3 (S)-(+)-methyl-(3-O--4-cyano)-butanoate 
• 138145-60-5 (R)-(-)-methyl-(3-O--4-cyano)-butanoate 

Relevant articles and documents

Copper-Catalyzed Syntheses of Multiple Functionalizatized Allenes via Three-Component Reaction of Enynes

A copper-catalyzed three-component reaction of cyclobutanone oxime esters and 1,3-enynes in the presence of TMSCN or TMSCF3 has been developed. This mild protocol enjoys a broad substrate scope tolerating many functional groups, providing a facile access to 1,7-double-functionalized allenes, which are difficult to prepare. The allenyl nitrile products may be easily transformed into allenoic acid derivatives and stereodefined tetrasubstituted alkenes, demonstrating their potentials as platform molecules in synthesis. A mechanism has been proposed on the basis of mechanistic studies.

Nitrile hydratase enzymes in organic synthesis: Enantioselective synthesis of the lactone moiety of the mevinic acids

(R)-4-Hydroxy-5-cyanopentene (-)-9, a known precursor of the protected lactone moiety of the mevinic acids 1, has been prepared in 9 steps from (S)-3-(benzyloxy)-4-cyanobutanoic acid 5 (88% e.e.) which was obtained by the asymmetric 2 step hydrolysis of 3-benzyloxyglutaronitrile 4 involving the successive activity of a nitrile hydratase and an amidase enzyme.

Stereoselective Hydrolysis of Nitriles and Amides Under Mild Conditions Using a Whole Cell Catalyst

An immobilised whole cell Rhodococcus sp. (SP 361) has been shown to be an effective catalyst for the stereoselective hydrolysis of both racemic and prochiral nitrile containing compounds. 2-Alkyl-arylacetonitriles 6a-8a were hydrolysed to (S)-acids and (R)-amides whereas the closely related substrate 9a gave the (R)-acid.A series of prochiral dinitriles 10a-13a were hydrolysed to the corresponding (S)-acids with e.e.'s 22-84percent.Models to account for the stereoselectivity of the enzymic hydrolyses have been proposed.