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Acetonitrile information


Acetonitrile
Skeletal formula of acetonitrile
Skeletal formula of acetonitrile
Skeletal formula of acetonitrile with all explicit hydrogens added
Skeletal formula of acetonitrile with all explicit hydrogens added
Ball and stick model of acetonitrile
Ball and stick model of acetonitrile
Spacefill model of acetonitrile
Spacefill model of acetonitrile
Names
Preferred IUPAC name
Acetonitrile[2]
Systematic IUPAC name
Ethanenitrile[2]
Other names
  • Cyanomethane[1]
  • Ethyl nitrile[1]
  • Methanecarbonitrile[1]
  • Methyl cyanide[1]
  • MeCN
  • ACN
Identifiers
CAS Number
  • 75-05-8 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
741857
ChEBI
  • CHEBI:38472 checkY
ChEMBL
  • ChEMBL45211 checkY
ChemSpider
  • 6102 checkY
ECHA InfoCard 100.000.760 Edit this at Wikidata
EC Number
  • 200-835-2
Gmelin Reference
895
MeSH acetonitrile
PubChem CID
  • 6342
RTECS number
  • AL7700000
UNII
  • Z072SB282N checkY
UN number 1648
CompTox Dashboard (EPA)
  • DTXSID7020009 Edit this at Wikidata
InChI
  • InChI=1S/C2H3N/c1-2-3/h1H3 checkY
    Key: WEVYAHXRMPXWCK-UHFFFAOYSA-N checkY
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 (S298)
149.62 J/(K·mol)
Std enthalpy of
formation fH298)
40.16–40.96 kJ/mol
Std enthalpy of
combustion cH298)
−1256.03 – −1256.63 kJ/mol
Hazards
GHS labelling:
Pictograms
GHS02: Flammable GHS07: Exclamation mark
Signal word
Danger
Hazard statements
H225, H302, H312, H319, H332
Precautionary statements
P210, P280, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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)[4]
LCLo (lowest published)
16,000 ppm (dog, 4 hr)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 40 ppm (70 mg/m3)[3]
REL (Recommended)
TWA 20 ppm (34 mg/m3)[3]
IDLH (Immediate danger)
500 ppm[3]
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).
checkY verify (what is checkY☒N ?)
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]

  1. ^ a b c d "Material Safety Data Sheet: Acetonitrile" (PDF). TedPella.com.
  2. ^ 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)
  3. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0006". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ a b "Acetonitrile". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  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.

and 23 Related for: Acetonitrile information

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Acetonitrile

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Acetonitrile, often abbreviated MeCN (methyl cyanide), is the chemical compound with the formula CH3CN and structure H3C−C≡N. This colourless liquid is...

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Transition metal nitrile complexes

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ligands in these complexes are often labile. Typical nitrile ligands are acetonitrile, propionitrile, and benzonitrile. The structures of [Ru(NH3)5(NCPh)]n+...

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Cyanide

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group is linked by a single covalent bond to carbon. For example, in acetonitrile (CH3−C≡N), the cyanide group is bonded to methyl (−CH3). Although nitriles...

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Indoleacetaldoxime dehydratase

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(indol-3-yl)acetonitrile + H2O Hence, this enzyme has one substrate, (indol-3-yl)acetaldehyde oxime, and two products, (indol-3-yl)acetonitrile and H2O....

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Aminoacetonitrile

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P.; Ott, J.; Thorwirth, S.; Hieret, C. (2008). "Detection of amino acetonitrile in Sgr B2(N)" (PDF). Astronomy and Astrophysics. 482 (1): 179–196. arXiv:0801...

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Pivalonitrile

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Flash point 4 °C (39 °F; 277 K) Related compounds Related alkanenitriles Acetonitrile Aminoacetonitrile Glycolonitrile Cyanogen Propanenitrile Aminopropionitrile...

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Acrylonitrile

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tonnes by 2017. Acetonitrile and hydrogen cyanide are significant byproducts that are recovered for sale. In fact, the 2008–2009 acetonitrile shortage was...

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Solvation

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polar solvent, but others exist, such as ethanol, methanol, acetone, acetonitrile, and dimethyl sulfoxide. Polar solvents are often found to have a high...

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Reference electrode

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turns out the platinum is rapidly poisoned by many solvents including acetonitrile causing uncontrolled drifts in potential. Both the SCE and saturated...

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Hypofluorous acid

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solution of hypofluorous acid in acetonitrile (generated in situ by passing gaseous fluorine through water in acetonitrile) Rozen's reagent. Hypofluorites...

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Extraterrestrial life

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Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Six atoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene...

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Urea

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2011). "Solubility of Urea in Acetonitrile–Water Mixtures and Liquid–Liquid Phase Separation of Urea-Saturated Acetonitrile–Water Mixtures". Journal of...

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Chlorphenamine

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2-chloropyridine in the presence of sodium amide to form 4-chlorophenyl(2-pyridyl)acetonitrile. Alkylating this with 2-dimethylaminoethylchloride in the presence of...

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Benzene

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Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Six atoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene...

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Scoville scale

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HPLC traces of dry samples of the substance to be tested in 1 ml of acetonitrile. The standard used to calibrate the calculation is 1 gram of capsaicin...

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Methane

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Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Six atoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene...

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Chloroacetonitrile

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compound with the formula ClCH2CN. A colorless liquid, it is derived from acetonitrile (CH3CN) by replacement of one H with Cl. In practice, it is produced...

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Tetrabutylammonium hexafluorophosphate

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It is highly soluble in polar organic solvents such as acetone and acetonitrile. The salt consists of a positively charged tetrabutylammonium, a quaternary...

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Molybdenum oxytetrafluoride

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The acetonitrile adduct of molybdenum oxytetrafluoride can be prepared by treating molybdenum hexafluoride with hexamethyldisiloxane in acetonitrile: MoF6...

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Water

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acetaldehyde, dimethylformamide, dimethoxyethane, dimethyl sulfoxide, acetonitrile. Partially miscible with diethyl ether, methyl ethyl ketone, dichloromethane...

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Methyl isocyanide

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methyl cyanide (acetonitrile), but its reactivity is very different. In contrast to the faintly sweet, ethereal odor of acetonitrile, the smell of methyl...

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Hydrogen chloride

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Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Six atoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene...

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Nitrous oxide

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Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Six atoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene...

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