Butyronitrile

Last updated
Butyronitrile [1]
Butyronitrile.png
Butyronitrile 3D ball.png
Names
Preferred IUPAC name
Butanenitrile [2]
Other names
  • 1-Cyanopropane [3]
  • Propyl cyanide [3]
  • n-Butyronitrile [3]
Identifiers
3D model (JSmol)
1361452
ChEBI
ChemSpider
ECHA InfoCard 100.003.365 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-700-6
MeSH N-butyronitrile
PubChem CID
RTECS number
  • ET8750000
UNII
UN number 2411
  • InChI=1S/C4H7N/c1-2-3-4-5/h2-3H2,1H3 X mark.svgN
    Key: KVNRLNFWIYMESJ-UHFFFAOYSA-N X mark.svgN
  • CCCC#N
Properties
C4H7N
Molar mass 69.107 g·mol−1
AppearanceColorless
Odor Sharp and suffocating [3]
Density 794 mg mL−1
Melting point −111.90 °C; −169.42 °F; 161.25 K
Boiling point 117.6 °C; 243.6 °F; 390.7 K
0.033 g/100 mL
Solubility soluble in benzene
miscible in alcohol, ether, dimethylformamide
Vapor pressure 3.1 kPa
190 μmol Pa−1 kg−1
−49.4·10−6 cm3/mol
1.38385
3.5
Thermochemistry
134.2 J K−1 mol−1
−6.8 – −4.8 kJ mol−1
−2.579 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg
Danger
H225, H301, H311, H331
P210, P261, P280, P301+P310, P311
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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
3
3
0
Flash point 18 °C (64 °F; 291 K)
488 °C (910 °F; 761 K)
Explosive limits 1.65%–? [3]
Lethal dose or concentration (LD, LC):
50 mg kg−1(oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
none [3]
REL (Recommended)
TWA 8 ppm (22 mg/m3) [3]
IDLH (Immediate danger)
N.D. [3]
Related compounds
Related alkanenitriles
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Butyronitrile or butanenitrile or propyl cyanide, is a nitrile with the formula C3H7CN. This colorless liquid is miscible with most polar organic solvents.

Contents

Uses

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

It also has recognized use in the synthesis of Etifelmine.

Synthesis

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

C3H7CH2OH + NH3 + O2 → C3H7CN + 3 H2O

Occurrence in space

Butyronitrile has been detected in the Large Molecule Heimat in Sagittarius B2 cloud along with other complex organic molecules. [5]

References

  1. ↑ Merck Index, 11th Edition, 1597
  2. ↑ "N-butyronitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 12 June 2012.
  3. 1 2 3 4 5 6 7 8 NIOSH Pocket Guide to Chemical Hazards. "#0086". National Institute for Occupational Safety and Health (NIOSH).
  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
  5. ↑ "Two highly complex organic molecules detected in space". Royal Astronomical Society. 21 April 2009. Retrieved 29 September 2015.
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