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Malononitrile information


Malononitrile
Skeletal formula of malononitrile
Ball-and-stick model
Ball-and-stick model
Space-filling model
Space-filling model
Names
IUPAC name
Malononitrile[2]
Preferred IUPAC name
Propanedinitrile[2]
Other names
Malonodinitrile, Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile[1]
Identifiers
CAS Number
  • 109-77-3 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
773697
ChEBI
  • CHEBI:33186 ☒N
ChemSpider
  • 13884495 ☒N
ECHA InfoCard 100.003.368 Edit this at Wikidata
EC Number
  • 203-703-2
Gmelin Reference
1303
MeSH dicyanmethane
PubChem CID
  • 8010
RTECS number
  • OO3150000
UNII
  • EBL1KKS93J checkY
UN number 2647
CompTox Dashboard (EPA)
  • DTXSID6021907 Edit this at Wikidata
InChI
  • InChI=1S/C3H2N2/c4-2-1-3-5/h1H2 ☒N
    Key: CUONGYYJJVDODC-UHFFFAOYSA-N ☒N
SMILES
  • N#CCC#N
Properties
Chemical formula
CH2(CN)2
Molar mass 66.063 g·mol−1
Appearance Colourless or white solid[1]
Density 1.049 g cm−3
Melting point 32 °C; 89 °F; 305 K
Boiling point 220.1 °C; 428.1 °F; 493.2 K
Solubility in water
13% (20 °C)[1][clarification needed]
Thermochemistry
Heat capacity (C)
110.29 J K−1 mol−1
Std molar
entropy (S298)
130.96 J K−1 mol−1
Std enthalpy of
formation fH298)
187.7 to 188.1 kJ mol−1
Std enthalpy of
combustion cH298)
−1,654.0 to −1,654.4 kJ mol−1
Hazards
GHS labelling:
Pictograms
GHS06: Toxic GHS09: Environmental hazard
Signal word
Danger
Hazard statements
H301, H311, H331, H410
Precautionary statements
P261, P273, P280, P301+P310, P311
Flash point 86 °C (187 °F; 359 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 19 mg kg−1 (oral, mouse)
  • 350 mg kg−1 (dermal, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
none[1]
REL (Recommended)
TWA 3 ppm (8 mg/m3)[1]
IDLH (Immediate danger)
N.D.[1]
Related compounds
Related alkanenitriles
  • Acetonitrile
  • Aminoacetonitrile
  • Glycolonitrile
  • Cyanogen
  • Propanenitrile
  • Aminopropionitrile
  • Pivalonitrile
  • Acetone cyanohydrin
  • Butyronitrile
  • Succinonitrile
  • Tetramethylsuccinonitrile
Related compounds
DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Malononitrile is an organic compound nitrile with the formula CH2(CN)2. It is a colorless or white solid, although aged samples appear yellow or even brown. It is a widely used building block in organic synthesis.

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0378". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 902. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

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Malononitrile

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Malononitrile is an organic compound nitrile with the formula CH2(CN)2. It is a colorless or white solid, although aged samples appear yellow or even...

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CS gas

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compound 2-chlorobenzalmalononitrile (also called o-chlorobenzylidene malononitrile; chemical formula: C10H5ClN2), a cyanocarbon, is the defining component...

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Phenacyl chloride

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mammalian toxicity of 1-chloroacetophenone (CN) and 2-chlorobenzylidene malononitrile (CS)". Archives of Toxicology. 40 (2): 75–95. doi:10.1007/BF01891962...

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Attica Correctional Facility

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within the New York state prisons. A CS gas system (chlorobenzylidine malononitrile) installed in the mess hall and industry areas has been used to quell...

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Amprolium

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may well involve conjugate addition of the amidine nitrogen to the malononitrile followed by loss of ethoxide (3); addition of the remaining amidine...

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Knoevenagel condensation

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condensation is demonstrated in this MORE synthesis with cyclohexanone, malononitrile and 3-amino-1,2,4-triazole: The Weiss–Cook reaction consists in the...

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Methylene bridge

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which contain methylene bridges include: Malonic acid Acetylacetone Malononitrile Methyl group Methylene group Methyne W. A. Herrmann (1982), "The methylene...

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CR gas

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its effects, CR gas is very similar to CS gas (o-chlorobenzylidene malononitrile), but twice as potent, even though there is little structural resemblance...

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Oxime

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with propiophenone, the reaction of phenacyl chloride, the reaction of malononitrile with sodium nitrite in acetic acid A conceptually related reaction is...

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Acetonitrile

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1-naphthaleneacetic acid. Its reaction with cyanogen chloride affords malononitrile. Acetonitrile has a free electron pair at the nitrogen atom, which can...

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Onion

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Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery)...

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Thyme

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Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery)...

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Dry media reaction

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solventless reaction is a Knoevenagel condensation of ketones with (malononitrile) where a 1:1 mixture of the two reactants (and ammonium acetate) is...

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List of chemical warfare agents

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chloroformate Dibenzoxazepine (CR) Ethyl iodoacetate Ortho-chlorobenzylidene malononitrile (Super tear gas; CS) Trichloromethyl chloroformate Xylyl bromide These...

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Tetracyanoethylene

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important member of the cyanocarbons. TCNE is prepared by brominating malononitrile in the presence of potassium bromide to give the KBr-complex, and dehalogenating...

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Oregano

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Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery)...

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Horseradish

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Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery)...

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Tear gas

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PMID 21649853. S2CID 205874180. Brvar M (February 2016). "Chlorobenzylidene malononitrile tear gas exposure: Rinsing with amphoteric, hypertonic, and chelating...

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Cinnamon

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Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery)...

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Formaldehyde

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Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery)...

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Rosemary

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Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery)...

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Turmeric

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Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery)...

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Tetrahydrocannabinol

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Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery)...

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EPA list of extremely hazardous substances

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dimethylcarbamate Lactonitrile Leptophos Lewisite Lindane Lithium hydride Malononitrile Manganese, tricarbonyl methylcyclopentadienyl Mechlorethamine Mercuric...

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Mentha

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Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery)...

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Sichuan pepper

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Cinnamaldehyde (cinnamon) CR gas (dibenzoxazepine; DBO) CS gas (2-chlorobenzal malononitrile) Cuminaldehyde (cumin) Curcumin (turmeric) Dehydroligustilide (celery)...

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Tricyanoaminopropene

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Tricyanoaminopropene (TRIAP, TCAP, malononitrile dimer, 1,1,3-tricyano-2-amino-1-propene) is a nootropic drug which mimics the function of nerve growth...

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