Malononitrile

Details

Stereochemistry	ACHIRAL
Molecular Formula	C3H2N2
Molecular Weight	66.0614
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N#CCC#N

InChI

InChIKey=CUONGYYJJVDODC-UHFFFAOYSA-N

InChI=1S/C3H2N2/c4-2-1-3-5/h1H2

HIDE SMILES / InChI

Molecular Formula	C3H2N2
Molecular Weight	66.0614
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4897955 | https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+2523 | https://jamanetwork.com/journals/archneurpsyc/article-abstract/650950 | https://www.scipress.com/ILCPA.57.126.pdf

Malononitrile is a weak cyanocarbon acid with exceptional reactivity. It is used extensively as a reactant or reaction intermediate since the methylene group and either one or both cyano groups can take part in condensation reactions to give a variety of additional products and heterocyclic compounds. This unique reactivity makes malononitrile an important chemical in research and in medical, industrial, and agricultural chemistry. In the late 1940's malononitrile was used experimentally in the treatment of schizophrenia and depression.

Approval Year

PubMed

Title	Date	PubMed
The effect of 5-alkyl modification on the biological activity of pyrrolo[2,3-d]pyrimidine containing classical and nonclassical antifolates as inhibitors of dihydrofolate reductase and as antitumor and/or antiopportunistic infection agents.	2008-08-14	18605720
Photochemical monoalkylation of propanedinitrile by electron-rich alkenes.	2008-07-03	18537243
Anti-inflammatory and analgesic activities of some newly synthesized pyridinedicarbonitrile and benzopyranopyridine derivatives.	2008-06	18515227
An efficient and facile synthesis of highly substituted 2,6-dicyanoanilines.	2008-05-02	18341285
Diammonium hydrogen phosphate as a versatile and efficient catalyst for the one-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives in aqueous media.	2008-05	18512127
Reduced band gap dithieno[3,2-b:2',3'-d]pyrroles: new n-type organic materials via unexpected reactivity.	2008-04-17	18348567
One-step synthesis of polysubstituted benzene derivatives by multi-component cyclization of alpha-bromoacetate, malononitrile and aromatic aldehydes.	2008-03-28	18338049
temperature-dependent orientational dynamics of 1,n-dicyano n-alkanes.	2008-03-13	18275183
The condensation of salicylaldehydes and malononitrile revisited: synthesis of new dimeric chromene derivatives.	2008-03-07	18271600
Novel three-component synthesis and antiproliferative properties of diversely functionalized pyrrolines.	2008-02-15	18221874
Highly enantioselective Michael addition of malononitrile to alpha,beta-unsaturated ketones.	2008-01-21	18175004
Reaction of 1-tert-butyl-3,4-diphenyl-1,2,4-triazol-5-ylidenes with a malonic ester.	2008-01-07	18075666
The tert-amino effect in heterocyclic chemistry: synthesis of new fused pyrazolinoquinolizine and 1,4-oxazinopyrazoline derivatives.	2007-12-12	18072979
An atom efficient, solvent-free, green synthesis and antimycobacterial evaluation of 2-amino-6-methyl-4-aryl-8-[(E)-arylmethylidene]-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitriles.	2007-12-01	17933535
[(2-Phenylindol-3-yl)methylene]propanedinitriles inhibit the growth of breast cancer cells by cell cycle arrest in G(2)/M phase and apoptosis.	2007-12-01	17889547
SmCl3-catalyzed C-acylation of 1,3-dicarbonyl compounds and malononitrile.	2007-10-25	17902683
Synthesis of C2-symmetric bisamidines: a new type of chiral metal-free Lewis acid analogue interacting with carbonyl groups.	2007-07-20	17585816
Antiproliferative and apoptosis inducing properties of pyrano[3,2-c]pyridones accessible by a one-step multicomponent synthesis.	2007-07-15	17512729
Efficient method for the synthesis of polysubstituted benzenes by one-pot tandem reaction of vinyl malononitriles with nitroolefins.	2007-07-06	17567078
Theoretical study on the ground and excited states of dicyanocarbene (C3N2) and its isomers: a low-temperature matrix emission spectrum attributable to 3-cyano-2H-azirenylidene.	2007-06-07	17497833
One-step synthesis of heterocyclic privileged medicinal scaffolds by a multicomponent reaction of malononitrile with aldehydes and thiols.	2007-04-27	17408286
Radical reactions of [60]fullerene mediated by manganese(III) acetate dihydrate.	2007-04-25	17450885
An improved procedure for the three-component synthesis of highly substituted pyridines using ionic liquid.	2007-04-13	17367198
Novel synthesis of [1]-benzothiepino[5,4-b]pyridine-3-carbonitriles and their anti-inflammatory properties.	2007-03-15	17267228
2-Arylhydrazononitriles as building blocks in heterocyclic synthesis: A novel route to 2-substituted-1,2,3-triazoles and 1,2,3-triazolo[4,5-b]pyridines.	2007-03-13	17355619
An efficient synthesis of pyrazolo[3,4-b]quinolin-3-amine and benzo[b][1,8]naphthyridine derivatives.	2007-03-08	17851395
Molecular diodes and ultra-thin organic rectifying junctions: Au-S-CnH2n-Q3CNQ and TCNQ derivatives.	2007-02-28	17301890
Vibrational fingerprint of the structural tuning in push-pull organic chromophores with quinoid or proaromatic spacers.	2007-02-21	17328621
Hydrogen sulfide, nitric oxide and a molecular mass 66 u substance in the exhaled breath of chronic pancreatitis patients.	2007	17912017
Michael additions of methylene active compounds to chalcone in ionic liquids without any catalyst: the peculiar properties of ionic liquids.	2007	17091517
Investigation of the excited state structure of DCM via ultrafast electronic pump/vibrational probe.	2006-09-28	16986894
Thiourea-catalyzed asymmetric michael addition of activated methylene compounds to alpha,beta-unsaturated imides: dual activation of imide by intra- and intermolecular hydrogen bonding.	2006-07-26	16848477
Synthesis of water-soluble, ring-substituted squaraine dyes and their evaluation as fluorescent probes and labels.	2006-06-16	17723402
Synthesis and molluscicidal activity of some 1,3,4-triaryl-5-chloropyrazole, pyrano[2,3-c]pyrazole, pyrazolylphthalazine and pyrano[2,3-d]thiazole derivatives.	2006-06	16649159
Cloning, overexpression, and characterization of a thermoactive nitrilase from the hyperthermophilic archaeon Pyrococcus abyssi.	2006-06	16495079
One-step, three-component synthesis of pyridines and 1,4-dihydropyridines with manifold medicinal utility.	2006-03-02	16494469
[Reaction of pyridinium salts with active methylene compounds].	2006-02	16462100
[Reaction of pyridinium and quinolinium salts having the leaving group at the 2- or 4-position with active methylene compounds].	2006-02	16462099
Novel milrinone analogs of pyridine-3-carbonitrile derivatives as promising cardiotonic agents.	2005-12	16040161
Physical properties and intermolecular dynamics of an ionic liquid compared with its isoelectronic neutral binary solution.	2005-10-27	16866386
Elastic, quasielastic, and inelastic neutron-scattering studies on the charge-transfer hexamethylbenzene-tetracyanoquinodimethane complex.	2005-09-22	16392480
A novel synthesis and molluscicidal activity of some functionally substituted pyridine, pyrido[3,2-c]pyridazine, and pyrido[3,2-c]pyridazino[2',3'-a]quinazoline derivatives.	2005-07	15981299
Prevention of CS "tear gas" eye and skin effects and active decontamination with Diphoterine: preliminary studies in 5 French Gendarmes.	2005-07	15961000
Extensive quinoidal oligothiophenes with dicyanomethylene groups at terminal positions as highly amphoteric redox molecules.	2005-06-29	15969551
Solvent-free mechanochemical and one-pot reductive benzylizations of malononitrile and 4-methylaniline using Hantzsch 1,4-dihydropyridine as the reductant.	2005-05-07	15858639
Individual and combined toxicity of nitriles and aldehydes to Raphidocelis subcapitata.	2005-05	16110983
Post-Hartree-Fock studies on the structure of bis(ortho-substituted phenyl)methylenes.	2005-02-10	16838962
Knoevenagel reaction in water catalyzed by amine supported on silica gel.	2005	16311808
Functionalization of pyrimidine and purine nucleosides at C4 and C6: C-nucleophilic substitution of their C4- and C6-(1,2,4-triazol-1-yl) derivatives.	2005	16248088
Synthesis and some reactions of 3-chloro-2-(cyanomethylene)-1,2-dihydroquinoxalines.	2004-03-31	18007426

Patents

Sample Use Guides

In Vivo Use Guide

In the late 1940's malononitrile was used experimentally in the treatment of schizophrenia and depression. ... Patients were given an intravenous infusion of 5% malononitrile for 10-69 min. The total dose during each treatment ranged from 1 to 6 mg/kg. Treatments were given 2-3 times/wk, with at least 1 day intervals. Ten to 20 min after the beginning of the infusion, all patients experienced tachycardia. In addition, redness, nausea, vomiting, headache, shivering, muscle spasms, & numbness were reported with varying frequency.

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:57:21 GMT 2025` Edited by `admin` on `Mon Mar 31 18:57:21 GMT 2025`
Record UNII	EBL1KKS93J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-3769

Preferred Name

English

Malononitrile

Systematic Name

English

Malonic dinitrile

Common Name

English

Cyanoacetonitrile

Systematic Name

English

Propanedinitrile

Systematic Name

English

Malononitrile [HSDB]

Common Name

English

Malononitrile [MI]

Common Name

English

Dicyanomethane

Systematic Name

English

Methylene cyanide

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

MALONONITRILE