Butyronitrile - Wikipedia

Có thể bạn quan tâm

Butyronitrile[1]

Names

Preferred IUPAC name Butanenitrile[3]

Other names

1-Cyanopropane[2]
Propyl cyanide[2]
n-Butyronitrile[2]

Identifiers

CAS Number

109-74-0 Y

3D model (JSmol)

Interactive image

Beilstein Reference

1361452

ChEBI

CHEBI:51937 N

ChemSpider

7717 N

ECHA InfoCard

100.003.365

EC Number

203-700-6

MeSH

N-butyronitrile

PubChem CID

8008

RTECS number

ET8750000

UNII

O3V36V0W0M Y

UN number

2411

CompTox Dashboard (EPA)

DTXSID1026823

InChI

InChI=1S/C4H7N/c1-2-3-4-5/h2-3H2,1H3 NKey: KVNRLNFWIYMESJ-UHFFFAOYSA-N N

SMILES

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 lawconstant (kH)

190 μmol Pa−1 kg−1

Magnetic susceptibility (χ)

−49.4·10−6 cm3/mol

Refractive index (nD)

1.38385

Dipole moment

3.5

Thermochemistry

Heat capacity (C)

134.2 J K−1 mol−1

Std enthalpy offormation (ΔfH⦵298)

−6.8 – −4.8 kJ mol−1

Std enthalpy ofcombustion (ΔcH⦵298)

−2.579 MJ mol−1

Hazards

GHS labelling:

Pictograms

Signal word

Danger

Hazard statements

H225, H301, H311, H331

Precautionary statements

P210, P261, P280, P301+P310, P311

NFPA 704 (fire diamond)

3 3 0

Flash point

18 °C (64 °F; 291 K)

Autoignitiontemperature

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

Isobutyronitrile
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).

verify (what is

?) Infobox references

Chemical compound

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]

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 ammoxidation of n-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]

^ 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.

External links

[edit]

NIST Chemistry WebBook page for C4H7N
CDC - NIOSH Pocket Guide to Chemical Hazards

Molecules detected in outer space

Molecules

Diatomic	Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Imidogen Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur mononitride Sulfur monoxide Titanium(II) oxide
Triatomic	Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene Methylidynephosphane N2H+ Nitrous oxide Nitroxyl Ozone Potassium cyanide Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Trihydrogen cation Water
Fouratoms	Acetylene Ammonia Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methyl cation Methyl radical Methylene amidogen Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thiocyanic acid Thioformaldehyde Tricarbon monosulfide Tricarbon monoxide
Fiveatoms	Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster
Sixatoms	Acetonitrile Cyanobutadiynyl radical Cyclopropenone Diacetylene E-Cyanomethanimine Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene
Sevenatoms	Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Methyl isocyanate Methylamine Propyne Vinyl alcohol
Eightatoms	Acetic acid Acrolein Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methyl formate Methylcyanoacetylene
Nineatoms	Acetamide Cyanohexatriyne Dimethyl ether Ethanethiol Ethanol Methyldiacetylene N-Methylformamide Octatetraynyl radical Propene Propionitrile
Tenatomsor more	Acetone Benzene Benzonitrile Buckminsterfullerene (C60, C60+, fullerene, buckyball) Butyronitrile C70 fullerene Cyanodecapentayne Ethyl formate Ethylene glycol Heptatrienyl radical Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Pyrimidine