131202-39-6

Basic information

• Product Name: 2-Propenenitrile, 2-(hydroxymethyl)-3-phenyl-, (2E)-
• CAS NO: 131202-39-6
• Molecular Formula: C10H9NO
• Molecular Weight: 159.188
• Mol File: 131202-39-6.mol

Chemical Properties

• CAS DataBase Reference: 2-Propenenitrile, 2-(hydroxymethyl)-3-phenyl-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenenitrile, 2-(hydroxymethyl)-3-phenyl-, (2E)-(131202-39-6)
• EPA Substance Registry System: 2-Propenenitrile, 2-(hydroxymethyl)-3-phenyl-, (2E)-(131202-39-6)

Safety Data

• Hazardous Substances Data: 131202-39-6(Hazardous Substances Data)

Upstream product

• 19362-96-0 2-(1-hydroxybenzyl)acrylonitrile 
• 116204-22-9 2-Hydroxymethyl-3-phenyl-oxirane-2-carbonitrile 
• 139413-81-3 2-(bromomethyl)-3-phenylprop-2-ene-nitrile 

Downstream Products

• 56069-64-8 2-Cyano-3-phenylpropenal 

Relevant articles and documents

A simple protocol for the synthesis of a piperidine-2,6-dione framework from Baylis-Hillman adducts

3-Hydroxy-2-methylenealkanenitriles, the Baylis-Hillman alcohols, derived from various aldehydes and acrylonitrile, have been conveniently transformed into 3-arylidene(or alkylidene)piperidine-2,6-diones in an operationally simple one-pot multi-step process involving Johnson-Claisen (J-C) rearrangement, partial hydrolysis, and cyclization. Rearranged Baylis-Hillman alcohols, (E)-2-hydroxymethyl-3-arylprop-2-enenitriles, have been converted into 4-aryl-3-methylidenepiperidine-2,6-diones in a similar reaction sequence. 4-Aryl-3,5-dimethylidenepiperidine-2,6-dione derivatives have been synthesized from Baylis-Hillman compounds, 3-aryl-4-cyano-2-methoxycarbonylpenta-1,4-dienes, obtained via the Baylis-Hillman reaction of methyl (2Z)-2-(bromomethyl)-3-arylprop-2-enoates with acrylonitrile, in a one-pot process.

Synthesis of stereochemically defined (E)-cinnamyl alcohol derivatives from the Baylis-Hillman adducts

The reaction of the Baylis-Hillman adducts 1a-g and trifluoroacetic acid at 30-70°C gave the rearranged cinnamyl alcohols 2a-g stereoselectively in moderate yields. (C) 2000 Elsevier Science Ltd.

Applications of the baylis-hillman adducts in organic synthesis: A facile synthesis of [E]-α-cyanocinnamyl alcohols and [E]-α-cyanocinnamic aldehydes

Aqueous sulfuric acid mediated transformation of the Baylis-Hillman adducts, i.e. 3-aryl-3-hydroxy-2-methylenepropanenitriles, into [E]-α- cyanocinnamyl alcohols and subsequent oxidation with PCC leading to the formation of stereochemically pure [E]-α-cya

A new and efficient method for the isomerization of secondary functional allylic alcohols into their primary isomers

The first efficient tandem: 'bromination-formylation-hydrolysis' for the 1,3-transposition of acyclic allylic alcohols 1 and 2 bearing a nitrile and an ester group is reported.

New efficient synthesis of 3-substituted 2-cyano allylic alcohols

An efficient tandem 'bromination-formylation-hydrolysis' mediated conversion of available 2-(1-hydroxy alkyl) acrylonitriles I to their corresponding 3-substituted 2-cyano allylic alcohols 2 is described.

A simple route to 3-substituted 2-cyano allylic alcohols

The first original and simple route to 3-substituted 2-cyano allylic alcohols with very good yields is described. The epoxide function in the key step acts as a protecting group during the synthesis of these allylic alcohols.