Butyronitrile

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Butyronitrile[1]
Structural formula of butyronitrile
Ball-and-stick model of the butyronitrile molecule
Names
IUPAC name
Butanenitrile[3]
Other names
  • 1-Cyanopropane[2]
  • Propyl cyanide[2]
  • n-Butyronitrile[2]
Identifiers
1361452
109-74-0 YesY
ChEBI CHEBI:51937 N
ChemSpider 7717 N
EC number 203-700-6
Jmol-3D images Image
MeSH N-butyronitrile
PubChem 8008
RTECS number ET8750000
UN number 2411
Properties
C4H7N
Molar mass 69.11 g·mol−1
Appearance Colourless
Odor sharp and suffocating[2]
Density 794 mg mL−1
Melting point −111.90 °C; −169.42 °F; 161.25 K
Boiling point 117 °C; 242 °F; 390 K
0.033 g/100 mL
Solubility soluble in benzene
miscible in alcohol, ether, dimethylformamide
Vapor pressure 3.1 Pa
190 μmol Pa−1 kg−1
1.38385
Dipole moment 3.5
Thermochemistry
134.2 J K−1 mol−1
−6.8–−4.8 kJ mol−1
−2.579 MJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H301, H311, H331
P210, P261, P280, P301+310, P311
EU Index 608-005-00-5
EU classification Highly Flammable F Toxic T
R-phrases R11, R23/24/25
S-phrases (S1/2), S16, S36/37, S45, S63
NFPA 704
Flammability code 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., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 18 °C (64 °F; 291 K)
488 °C (910 °F; 761 K)
Explosive limits 1.65%–?[2]
50 mg kg−1 (oral, rat)
US health exposure limits (NIOSH):
none[2]
TWA 8 ppm (22 mg/m3)[2]
N.D.[2]
Related compounds
Related alkanenitriles
Related compounds
DBNPA
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Butyronitrile or butanenitrile or propyl cyanide, is a nitrile with the formula C3H7CN. This colorless liquid is miscible with most polar organic solvents.

Uses[edit]

It is mainly used as a precursor to the poultry drug amprolium.[4]

Synthesis[edit]

Butyronitrile is prepared industrially by the ammoxidation of n-butanol:

C3H7CH2OH + NH3 + O2 → C3H7CN + 3 H2O


References[edit]

  1. ^ Merck Index, 11th Edition, 1597
  2. ^ a b c d e f g h "NIOSH Pocket Guide to Chemical Hazards #0086". National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ "N-butyronitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 12 June 2012. 
  4. ^ Peter Pollak, Gérard Romeder, Ferdinand Hagedorn, Heinz-Peter Gelbke "Nitriles" Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a17_363

External links[edit]