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Butyronitrile





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Butyronitrileorbutanenitrileorpropyl cyanide, is a nitrile with the formula C3H7CN. This colorless liquid is miscible with most polar organic solvents.

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

    CAS Number

    3D model (JSmol)

    Beilstein Reference

    		 1361452
    ChEBI
    ChemSpider
    ECHA InfoCard 100.003.365 Edit this at Wikidata
    EC Number
    • 203-700-6
    MeSH N-butyronitrile

    PubChem CID
    RTECS number
    • ET8750000
    UNII
    UN number 2411

    CompTox Dashboard (EPA)

    • InChI=1S/C4H7N/c1-2-3-4-5/h2-3H2,1H3 ☒N

      Key: KVNRLNFWIYMESJ-UHFFFAOYSA-N ☒N

    • CCCC#N

    Properties

    Chemical formula

    		 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

    Solubility in water

    		 0.033 g/100 mL
    Solubility soluble in benzene
    miscible in alcohol, ether, dimethylformamide
    Vapor pressure 3.1 kPa

    Henry's law
    constant     (kH)

    		 190 μmol Pa−1kg−1

    Magnetic susceptibility (χ)

    		 -49.4·10−6cm3/mol

    Refractive index (nD)

    		 1.38385

    Dipole moment

    		 3.5
    Thermochemistry

    Heat capacity (C)

    		 134.2 J K−1 mol−1

    Std enthalpy of
    formation     (ΔfH⦵298)

    		 −6.8–−4.8 kJ mol−1

    Std enthalpy of
    combustion     (ΔcH⦵298)

    		 −2.579 MJ mol−1
    Hazards
    GHS labelling:

    Pictograms

    		 GHS02: Flammable GHS06: Toxic

    Signal word

    		 Danger

    Hazard statements

    		 H225, H301, H311, H331

    Precautionary statements

    		 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)

    Autoignition
    temperature

    		 488 °C (910 °F; 761 K)
    Explosive limits 1.65%–?[2]
    Lethal dose or concentration (LD, LC):

    LD50 (median dose)

    		 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
  • Propanenitrile
  • Malononitrile
  • Pivalonitrile
  • Succinonitrile
  • Glutaronitrile

    • Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    ☒N verify (what is checkY☒N ?)

    Infobox references

    Uses

    edit

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

    It also has recognized use in the synthesis of Etifelmine.

    Synthesis

    edit

    Butyronitrile is prepared industrially by the ammoxidationofn-butanol:

    C3H7CH2OH + NH3 + O2 → C3H7CN + 3 H2O

    Occurrence in space

    edit

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

    References

    edit
    1. ^ Merck Index, 11th Edition, 1597
  • ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0086". National Institute for Occupational Safety and Health (NIOSH).
  • ^ "N-butyronitrile - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 12 June 2012.
  • ^ 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
  • ^ "Two highly complex organic molecules detected in space". Royal Astronomical Society. 21 April 2009. Retrieved 29 September 2015.
    • edit

    Retrieved from "https://en.wikipedia.org/w/index.php?title=Butyronitrile&oldid=1167504180"
      



    Last edited on 28 July 2023, at 04:36  





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    ●This page was last edited on 28 July 2023, at 04:36 (UTC).
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