Acetonitrile

Acetonitrile
Skeletal formula of acetonitrile	Skeletal formula of acetonitrile with all explicit hydrogens added
Ball and stick model of acetonitrile	Spacefill model of acetonitrile
Names
	Preferred IUPAC name Acetonitrile
	Systematic IUPAC name Ethanenitrile
	Other names Cyanomethane; Ethyl nitrile; Methanecarbonitrile; Methyl cyanide; MeCN; ACN;
Identifiers
CAS Number	75-05-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	741857
ChEBI	CHEBI:38472 ;
ChEMBL	ChEMBL45211 ;
ChemSpider	6102 ;
ECHA InfoCard	100.000.760
EC Number	200-835-2;
Gmelin Reference	895
MeSH	acetonitrile
PubChem CID	6342;
RTECS number	AL7700000;
UNII	Z072SB282N ;
UN number	1648
CompTox Dashboard (EPA)	DTXSID7020009 ;
	InChI InChI=1S/C2H3N/c1-2-3/h1H3 Key: WEVYAHXRMPXWCK-UHFFFAOYSA-N ;
	SMILES CC#N;
Properties
Chemical formula	C2H3N
Molar mass	41.053 g·mol−1
Appearance	Colorless liquid
Odor	Faint, distinct, fruity
Density	0.786 g/cm3 at 25°C
Melting point	−46 to −44 °C; −51 to −47 °F; 227 to 229 K
Boiling point	81.3 to 82.1 °C; 178.2 to 179.7 °F; 354.4 to 355.2 K
Solubility in water	Miscible
log P	−0.334
Vapor pressure	9.71 kPa (at 20.0 °C)
Henry's law; constant (kH)	530 μmol/(Pa·kg)
Acidity (pKa)	25
UV-vis (λmax)	195 nm
Absorbance	≤0.10
Magnetic susceptibility (χ)	−28.0×10−6 cm3/mol
Refractive index (nD)	1.344
Dipole moment	3.92 D
Thermochemistry
Heat capacity (C)	91.69 J/(K·mol)
Std molar; entropy (S⦵298)	149.62 J/(K·mol)
Std enthalpy of; formation (ΔfH⦵298)	40.16–40.96 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	−1256.03 – −1256.63 kJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H312, H319, H332
Precautionary statements	P210, P280, P305+P351+P338
NFPA 704 (fire diamond)	2 3 0
Flash point	2.0 °C (35.6 °F; 275.1 K)
Autoignition; temperature	523.0 °C (973.4 °F; 796.1 K)
Explosive limits	4.4–16.0%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	2 g/kg (dermal, rabbit); 2.46 g/kg (oral, rat);
LC50 (median concentration)	5655 ppm (guinea pig, 4 hr); 2828 ppm (rabbit, 4 hr); 53,000 ppm (rat, 30 min); 7500 ppm (rat, 8 hr); 2693 ppm (mouse, 1 hr)
LCLo (lowest published)	16,000 ppm (dog, 4 hr)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 40 ppm (70 mg/m3)
REL (Recommended)	TWA 20 ppm (34 mg/m3)
IDLH (Immediate danger)	500 ppm
Related compounds
Related alkanenitriles	Hydrogen cyanide; Thiocyanic acid; Cyanogen iodide; Cyanogen bromide; Cyanogen chloride; Cyanogen fluoride; Aminoacetonitrile; Glycolonitrile; Cyanogen; Propionitrile; Aminopropionitrile; Malononitrile; Pivalonitrile; Acetone cyanohydrin;
Related compounds	DBNPA
Supplementary data page
	Acetonitrile (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula CH₃CN and structure H₃C−C≡N. This colourless liquid is the simplest organic nitrile (hydrogen cyanide is a simpler nitrile, but the cyanide anion is not classed as organic). It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene.^[5] The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.^[6]

Acetonitrile was first prepared in 1847 by the French chemist Jean-Baptiste Dumas.^[7]

^ ^a ^b ^c ^d "Material Safety Data Sheet: Acetonitrile" (PDF). TedPella.com.
^ ^a ^b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 902. doi:10.1039/9781849733069-FP001 (inactive 2024-05-06). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of May 2024 (link)
^ ^a ^b ^c NIOSH Pocket Guide to Chemical Hazards. "#0006". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b "Acetonitrile". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ "Archived copy" (PDF). Ashford's Dictionary of Industrial Chemicals, Third edition. p. 76. Archived from the original (PDF) on 2011-05-16. Retrieved 2011-03-31.{{cite web}}: CS1 maint: archived copy as title (link)
^ Karakida, Ken'ichi; Fukuyama, Tsutomu; Kuchitsu, Kozo (1974). "Molecular Structures of Hydrogen Cyanide and Acetonitrile as Studied by Gas Electron Diffraction". Bulletin of the Chemical Society of Japan. 47 (2): 299–304. doi:10.1246/bcsj.47.299.
^ Dumas, J.-B. (1847). "Action de l'acide phosphorique anhydre sur les sels ammoniacaux" [Action of anhydrous phosphoric acid on ammonium salts]. Comptes rendus. 25: 383–384.

[Pella-1] "Material Safety Data Sheet: Acetonitrile" (PDF). TedPella.com.

[iupac2013-2] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 902. doi:10.1039/9781849733069-FP001 (inactive 2024-05-06). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of May 2024 (link)

[NIOSH-3] NIOSH Pocket Guide to Chemical Hazards. "#0006". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-4] "Acetonitrile". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[ashford-5] "Archived copy" (PDF). Ashford's Dictionary of Industrial Chemicals, Third edition. p. 76. Archived from the original (PDF) on 2011-05-16. Retrieved 2011-03-31.{{cite web}}: CS1 maint: archived copy as title (link)

[6] Karakida, Ken'ichi; Fukuyama, Tsutomu; Kuchitsu, Kozo (1974). "Molecular Structures of Hydrogen Cyanide and Acetonitrile as Studied by Gas Electron Diffraction". Bulletin of the Chemical Society of Japan. 47 (2): 299–304. doi:10.1246/bcsj.47.299.

[7] Dumas, J.-B. (1847). "Action de l'acide phosphorique anhydre sur les sels ammoniacaux" [Action of anhydrous phosphoric acid on ammonium salts]. Comptes rendus. 25: 383–384.

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