Valeronitrile

Valeronitrile Basic information
Product Name:Valeronitrile
Synonyms:N-VALERONITRILE;NITRILE C5;PENTANE NITRILE;VALERONITRILE;BUTYL CYANIDE;1-Butyl cyanide;1-butylcyanide;1-Cyanbutan
CAS:110-59-8
MF:C5H9N
MW:83.13
EINECS:203-781-8
Product Categories:Building Blocks;C1 to C5;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
Mol File:110-59-8.mol
Valeronitrile Structure
Valeronitrile Chemical Properties
Melting point −96 °C(lit.)
Boiling point 139-141 °C(lit.)
density 0.795 g/mL at 25 °C(lit.)
vapor pressure 7.0 hPa (20 °C)
refractive index n20/D 1.397(lit.)
Fp 105 °F
storage temp. Store below +30°C.
solubility 10.0g/l
form Liquid
color Clear colorless
Water Solubility 0.1-0.5 g/100 mL at 22.5 ºC
Merck 14,9905
BRN 1736706
Exposure limitsNIOSH: IDLH 25 mg/m3
Stability:Stable. Incompatible with strong acids, strong bases, strong oxidizing agents, strong reducing agents. Flammable.
InChIKeyRFFFKMOABOFIDF-UHFFFAOYSA-N
LogP1.120
CAS DataBase Reference110-59-8(CAS DataBase Reference)
NIST Chemistry ReferencePentanenitrile(110-59-8)
EPA Substance Registry SystemValeronitrile (110-59-8)
Safety Information
Hazard Codes T
Risk Statements 10-25-2017/10/25
Safety Statements 36/37/39-45-16
RIDADR UN 1992 3/PG 3
WGK Germany 3
RTECS YV8195000
Autoignition Temperature520 °C
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29269095
HS Code 29332100
ToxicityLD50 orally in male mice: 2.297 mmol/kg (Tanii)
MSDS Information
ProviderLanguage
Pentanenitrile English
SigmaAldrich English
ACROS English
ALFA English
Valeronitrile Usage And Synthesis
Chemical PropertiesClear liquid
UsesValeronitrile is used as building block in organic synthesis. Product Data Sheet
UsesSolvent.
UsesValeronitrile is used in the preparation of valeric acid. It is also used to enhance the nitrilase activity in many strains.
Production MethodsValeronitrile can be synthesized by dehydration of valeronamide. The nitrile is also found in nature and is a constituent of coal gasification and oil shale processing waste water, sewage wastewater and tobacco smoke.
DefinitionChEBI: Pentanenitrile is a nitrile.
General DescriptionClear colorless to yellow liquid.
Air & Water ReactionsSlightly soluble in water.
Reactivity ProfileNitriles, such as Valeronitrile, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids. Valeronitrile is incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents. .
Health HazardValeronitrile is an irritant and may be harmful by inhalation, ingestion or skin absorption .
Fire HazardValeronitrile is combustible.
Industrial usesValeronitrile is used as an industrial solvent and as a chemical intermediate.
ToxicologyPentanenitrile is toxic to animals, and produces its action by the liberation of cyanide by cytochrome P450. The cyanide is detoxified and excreted in urine as thiocyanate.
MetabolismAs with other aliphatic nitriles, valeronitrile is metabolized in vivo resulting in the liberation of cyanide ion which is responsible for much of the observed toxicity of this compound . Biotransformation of valeronitrile presumably proceeds in a manner similar to that of other aliphatic nitriles with an initial cytochrome P-450 catalyzed oxidation of the nitrile to the cyanohydrin followed by release of the cyanide group from the activated molecule. Cyanide formation was significantly reduced when valeronitrile was incubated with mouse hepatic microsomes in the presence of SKF-525A or carbon monoxide or when microsomes from mice pretreated with chloroform were used . Ethanol pretreatment of mice markedly increases the in vivo and in vitro microsomal oxidation of valeronitrile presumably as a result of increased levels of an ethanol inducible cytochrome P-450 . As with other nitriles, the cyanide released upon biotransformation of valeronitrile is readily converted to thiocyanate in vivo and the latter ion was the major urinary excretion product observed with valero-nitrile in rats . From 18 to 31% of a daily 175 mg/kg dose of valeronitrile was eliminated in the urine as thiocyanate during a 24 h period. In another study , 43.2 and 27.5%, respectively, of an oral or i.p. dose of 0.75 mmol/kg valeronitrile was excreted as thiocyanate in the urine of male Sprague-Dawley rats over a 24 h period.
Purification MethodsWash the nitrile with half its volume of conc HCl (twice), then with saturated aqueous NaHCO3, dry it with MgSO4 and fractionally distil it from P2O5. [Beilstein 2 H 301, 2 I 131, 2 II 267, 2 III 675, 2 IV 875.]
Structure and conformationThe valeronitrile molecule is flexible and can adopt a number of different conformers, so that it will naturally be a mixture. These conformers are called anti-anti (30%), anti-gauche (46%), gauche-anti, gauche-gauche-cis, and gauche-gauche-trans.
2-(3,4-Dimethoxyphenyl)-2-isopropyl-5-(3,4-dimethoxyphenethylamino)valeronitrile 5-BROMOVALERONITRILE CYCLOBUTANE-1,2-DICARBONITRILE 5-OXO-5-(4-TRIFLUOROMETHYLPHENYL)VALERONITRILE 4-Methoxy-2,4-dimethyl-2-[N'-(p-tolyl)hydrazino]valeronitrile 1-Cyclohexene-1-acetonitrile piperidine-1-valeronitrile [S,(-)]-2-(3,4-Dimethoxyphenyl)-2-isopropyl-5-[[2-(3-methoxyphenyl)ethyl]methylamino]valeronitrile 2,4-Dimethyl-4-methoxy-2-(p-tolylazo)valeronitrile 2-Isobutyl-4-methyl-2-(N'-phenylhydrazino)valeronitrile 1-CYCLOPENTENYLACETONITRILE CYCLOPENTANECARBONITRILE 2-OXOOCTANENITRILE 4-methyl-2-oxopentanenitrile 2,4-Dimethyl-2-(N'-phenylhydrazino)valeronitrile Cyanide 4-Methoxy-2,4-dimethyl-2-(N'-phenylhydrazino)valeronitrile 2,2'-Azodi(2-methylbutyronitrile)

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