ALLYL CYANIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H5N
Molecular Weight	67.0892
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C=CCC#N

InChI

InChIKey=SJNALLRHIVGIBI-UHFFFAOYSA-N

InChI=1S/C4H5N/c1-2-3-4-5/h2H,1,3H2

HIDE SMILES / InChI

Molecular Formula	C4H5N
Molecular Weight	67.0892
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Vestibulotoxic properties of potential metabolites of allylnitrile.	2013-09	23761299
Role of CYP2E1-mediated metabolism in the acute and vestibular toxicities of nineteen nitriles in the mouse.	2012-01-25	22051853
Direct catalytic asymmetric addition of allyl cyanide to ketones via soft Lewis acid/hard Brønsted base/hard Lewis base catalysis.	2010-04-21	20337453
Preconditioning with subneurotoxic allyl nitrile: protection against allyl nitrile neurotoxicity.	2010-02	20034531
Synthesis and application of modular phosphine-phosphoramidite ligands in asymmetric hydroformylation: structure-selectivity relationship.	2010-01-18	19950337
Elementary reactions and their role in gas-phase prebiotic chemistry.	2009-05-19	19564951
Direct catalytic asymmetric addition of allyl cyanide to ketones.	2009-03-11	19215140
Allylnitrile metabolism by CYP2E1 and other CYPs leads to distinct lethal and vestibulotoxic effects in the mouse.	2009-02	18990727
Direct catalytic asymmetric addition of allylic cyanides to ketoimines.	2008-11-05	18844357
Reaction dynamics on the formation of 1- and 3-cyanopropylene in the crossed beams reaction of ground-state cyano radicals (CN) with propylene (C3H6) and its deuterated isotopologues.	2008-10-02	18681396
Modular chiral bidentate phosphonites: design, synthesis, and application in catalytic asymmetric hydroformylation reactions.	2008	18624296
Adsorption of 125I-labeled immunoglobulin G, its F(ab')2 and Fc fragments onto plasma-polymerized films.	2007-05-15	17118644
Changes in glucosinolate concentrations, myrosinase activity, and production of metabolites of glucosinolates in cabbage (Brassica oleracea Var. capitata) cooked for different durations.	2006-10-04	17002432
Induction of detoxication enzymes in mice by naturally occurring allyl nitrile.	2005-11-16	16277393
Surface reactions of 3-butenenitrile on the Si(001)-2 x 1 surface at room temperature.	2005-07-07	16852601
Binolam-AlCl: a two-centre catalyst for the synthesis of enantioenriched cyanohydrin O-phosphates.	2005-06-20	15776489
Synthesis of unsaturated amino alcohols through unexpectedly selective Ru-catalyzed cross-metathesis reactions.	2005-05-26	15901147
Highly active, regioselective, and enantioselective hydroformylation with Rh catalysts ligated by Bis-3,4-diazaphospholanes.	2005-04-13	15810837
Parallel ligand screening on olefin mixtures in asymmetric hydroformylation reactions.	2004-09-16	15355031
Synthesis and application of a new bisphosphite ligand collection for asymmetric hydroformylation of allyl cyanide.	2004-06-11	15176828
Kinetics, thermodynamics, and effect of BPh3 on competitive C-C and C-H bond activation reactions in the interconversion of allyl cyanide by [Ni(dippe)].	2004-03-24	15025492
Allylnitrile: generation from cruciferous vegetables and behavioral effects on mice of repeated exposure.	2004-03	14871587
In vitro digestion of sinigrin and glucotropaeolin by single strains of Bifidobacterium and identification of the digestive products.	2004-03	14871576
Pi-halogen dimer interactions and the inclusion chemistry of a new tetrahalo aryl host.	2004-01-21	14737639
Removal of nitriles from synthetic wastewater by acrylonitrile utilizing bacteria.	2004	15242125
Competition and selectivity in the reaction of nitriles on ge(100)-2x1.	2003-04-23	12696912
Plant-derived biomolecules in fermented cabbage.	2002-11-06	12405778
The effect of chlorination on organocyanide compounds.	2002-05-09	11995867
Glucosinolate breakdown products as insect fumigants and their effect on carbon dioxide emission of insects.	2002-03-22	11914158
[Determination of isothiocyanates and related compounds in mustard extract and horseradish extract used as natural food additives].	2002-02	11998313
Biodegradation of glucosinolates in brown mustard seed meal (Brassica juncea) by Aspergillus sp. NR-4201 in liquid and solid-state cultures.	2002	12713131
Behavioural disturbances and sensory pathology following allylnitrile exposure in rats.	2001-06-22	11406128
Enzymatic characterization of the recombinant Arabidopsis thaliana nitrilase subfamily encoded by the NIT2/NIT1/NIT3-gene cluster.	2001-03	11525507
The ototoxic effects induced in rats by treatment for 12 weeks with 2-butenenitrile, 3-butenenitrile and cis-2-pentenenitrile.	2001-03	11245407

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:16:54 GMT 2025` Edited by `admin` on `Mon Mar 31 19:16:54 GMT 2025`
Record UNII	527U1WJJ18
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALLYL CYANIDE

Systematic Name

English

NSC-2583

Preferred Name

English

.BETA.-BUTENONITRILE

Systematic Name

English

ALLYL CYANIDE [MI]

Common Name

English

VINYLACETONITRILE

Systematic Name

English

3-BUTENENITRILE

Systematic Name

English

Code System Code Type Description

SMS_ID

300000053082