Butyronitrile

Butyronitrile[1]
Structural formula of butyronitrile
Ball-and-stick model of the butyronitrile molecule
Names
Preferred IUPAC name
Butanenitrile[3]
Other names
  • 1-Cyanopropane[2]
  • Propyl cyanide[2]
  • n-Butyronitrile[2]
Identifiers
3D model (JSmol)
1361452
ChEBI
ChemSpider
ECHA InfoCard 100.003.365
EC Number
  • 203-700-6
MeSH N-butyronitrile
RTECS number
  • ET8750000
UNII
UN number 2411
  • InChI=1S/C4H7N/c1-2-3-4-5/h2-3H2,1H3 ☒N
    Key: KVNRLNFWIYMESJ-UHFFFAOYSA-N ☒N
  • CCCC#N
Properties
C4H7N
Molar mass 69.107 g·mol−1
Appearance Colorless
Odor Sharp and suffocating[2]
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:
GHS02: Flammable GHS06: Toxic
Danger
H225, H301, H311, H331
P210, P261, P280, P301+P310, P311
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 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%–?[2]
Lethal dose or concentration (LD, LC):
50 mg kg−1 (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[2]
REL (Recommended)
 TWA 8 ppm (22 mg/m3)[2]
IDLH (Immediate danger)
 N.D.[2]
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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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

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. ^ 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
  5. ^ "Two highly complex organic molecules detected in space". Royal Astronomical Society. 21 April 2009. Retrieved 29 September 2015.
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