Isobutyronitrile

Isobutyronitrile Basic information
Product Name:Isobutyronitrile
Synonyms:Isobutylronitrile;#niso-Butyronitrile;ISOBUTYRONITRILE, 99.6%;1-Cyano-1-methylethane;2-Cyanopropane;2-methyl-propanenitril;2-methyl-propanoicacinitrile;alpha-Methylpropanenitrile
CAS:78-82-0
MF:C4H7N
MW:69.11
EINECS:201-147-5
Product Categories:Organics
Mol File:78-82-0.mol
Isobutyronitrile Structure
Isobutyronitrile Chemical Properties
Melting point -72 °C (lit.)
Boiling point 107-108 °C (lit.)
density 0.770 g/mL at 20 °C (lit.)
vapor density 2.38 (vs air)
vapor pressure 100 mm Hg ( 54.4 °C)
refractive index n20/D 1.372(lit.)
Fp 39 °F
storage temp. Flammables area
solubility slightly soluble in water and acetone, very soluble in alcohol and ether
form Liquid
color Clear colorless to light yellow
Water Solubility 35 g/L (20 ºC)
Merck 14,5156
BRN 1340512
Stability:Stable. Flammable. May form explosive mixtures with air. Incompatible with strong oxidizing agents.
CAS DataBase Reference78-82-0(CAS DataBase Reference)
NIST Chemistry ReferencePropanenitrile, 2-methyl-(78-82-0)
EPA Substance Registry SystemIsobutyronitrile (78-82-0)
Safety Information
Hazard Codes F,T
Risk Statements 11-23/24/25-36/37/38
Safety Statements 9-16-24/25-26-36/37/39-45-23
RIDADR UN 2284 3/PG 2
WGK Germany 2
RTECS TZ4900000
Hazard Note Highly Flammable/Toxic
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29269095
Hazardous Substances Data78-82-0(Hazardous Substances Data)
ToxicityLD50 (mg/kg): 25 i.p. in mice; 200 orally in rats (Zeller); LD50 orally in male mice: 0.3652 mmol/kg (Tanii)
MSDS Information
ProviderLanguage
SigmaAldrichEnglish
ALFAEnglish
Isobutyronitrile Usage And Synthesis
Chemical PropertiesColorless liquid with a foul odor. Insoluble in water, easily soluble in ethanol and ether.
UsesIsobutyronitrile can be derived from isobutyraldehyde. It is used in organic synthesis, as a catalyst in the polymerization of ethylene and in the petroleum industry as a gasoline additive. Isobutyronitrile is also used to synthesize the intermediate 2-isopropyl-4-methyl-6-hydroxypyrimidine of the organophosphorus insecticide diazinon.
Production MethodsIsobutyronitrile is prepared from isobutyraldehyde by cyanation with ammonia.
DefinitionChEBI: Isobutyronitrile is an aliphatic nitrile that is acetonitrile in which two of the hydrogens have been replaced by methyl groups. It has a role as a polar aprotic solvent. It is an aliphatic nitrile and a volatile organic compound.
General DescriptionA clear colorless liquid. Flash point 47°F. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.
Air & Water ReactionsHighly flammable. Slightly soluble in water.
Reactivity ProfileIsobutyronitrile is incompatible with the following: Oxidizers, reducing agents, strong acids & bases .
HazardToxic by ingestion, inhalation, and skin absorption.
Health HazardIsobutyronitrile is considered highly hazardous and full precautions should be taken to prevent skin contact or inhalation of vapor. Inhaled isobutyronitrile is about 2.4 times as toxic as acetonitrile in rats. may be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes. (Non-Specific — Nitriles) Primarily, they are skin and eye irritants. Large doses cause collapse and stop breathing. In order to protect workers, the recommended TWA limit is obtained by dividing that for acetonitrile by the factor 2.4. NIOSH has therefore recommended that employee exposure should not exceed 8 p.p.m. (22 mg/m3) for either compound as a TLV-TWA.
Fire HazardVapor may explode if ignited in an enclosed area. Toxic oxides of nitrogen are produced during combustion. Isobutyronitrile is a flammable/combustible material and may be ignited by heat, sparks, or flames. Vapors may travel to a source of ignition and flash back. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Hazardous polymerization may not occur.
MetabolismThiocyanate was present in the urine of rats dosed orally with isobutyronitrile.
Purification MethodsShake the nitrile with conc HCl (to remove isonitriles), then with water and aqueous NaHCO3. After a preliminary drying with silica gel or Linde type 4A molecular sieves, it is shaken or stirred with CaH2 until hydrogen evolution ceases, then decanted and distilled from P2O5 (not more than 5g/L, to minimize gel formation) or Drierite (b 101-103o/760mm). Finally it is refluxed with, and slowly distilled from CaH2 (5g/L), taking precautions to exclude moisture. [Beilstein 2 H 294, 2 I 129, 2 II 263, 2 III 655, 2 IV 853.]
Isobutyronitrile Preparation Products And Raw materials
Raw materialsIsobutylene–>2-Methyl-1-propanol–>Isobutyraldehyde–>Zinc sulphate–>HYDROGEN CYANIDE–>Isobutylamine–>Isobutyramide
Preparation ProductsIsobutyric acid–>L-Valine–>Diazinon–>VALERATE–>2-ISOPROPYL-6-METHYL-4-PYRIMIDINOL–>Ethyl isovalerate–>2-METHYLPROPANIMIDAMIDE HYDROCHLORIDE–>Bladex–>Benzeneacetonitrile, 2-fluoro-alpha,alpha-dimethyl-–>2-chloro-2-methylpropiononitrile–>4-Amino-2,4-dihydro-5-(1-methylethyl)-3H-1,2,4-triazol-3-one

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