4-Pentenenitrile (HCID 11604)

Overview

4-pentenenitrile has been reported in Brassica napus with data available.

Names & identifiers

Preferred name: 4-Pentenenitrile
IUPAC: pent-4-enenitrile
English name: 4-Pentenenitrile
Molecular formula: C5H7N
Molecular weight: 81.12

Names & synonyms

4-PENTENENITRILE592-51-8Allylacetonitrile3-Butenyl cyanide1-Cyano-3-butene4-Cyano-1-butene4-PentenonitrileAllylmethyl cyanide4-Pentenoic acid, nitrileDTXSID002722889HYM37372DTXCID907228

Show more names

3-butenylcyanideallylmethylcyanide4-Pentenenitrile>4-Pentenenitrile 97%

4 pentenenitrileRefChem:526246209-762-0pent-4-enenitrileMFCD00151259HSDB 5709EINECS 209-762-0UNII-89HYM37372

Database identifiers

CAS: 592-51-8
PubChem CID: 11604
DTXSID: DTXSID0027228
ChEMBL: CHEMBL1595985
UNII: 89HYM37372
EC Number: 209-762-0
Nikkaji: J45.897J

Properties

Computed structural properties

XLogP: 1
Topological polar surface area: 23.8 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 2
Heavy atoms: 6
Formal charge: 0
Complexity: 75.2

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Nitriles

SpringerMaterials PropertiesOptical coefficient

Density0.8239 AT 24 °C

SolubilityINSOL IN WATER; MISCIBLE WITH ALCOHOL, ETHER

Boiling Point140 °C

Vapor Pressure6.36 [mmHg]

Physicochemical properties

Melting point: 138 · 138-139 °C
Boiling point: 140 °C · 140 °C (lit.)
Density: 0.814 g/mL · 0.814 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.42(lit.)
Flash point: 140 °F · 140 °F
storage temp.: 2 · 2-8°C
Water Solubility: Insoluble in water
form: clear liquid
color: Colorless to Almost colorless
Stability: Stable. Flammable. Incompatible with strong oxidizing agents. May generate toxic gases in a fire.
InChI: 1S/C5H7N/c1-2-3-4-5-6/h2H,1,3-4H2
InChIKey: CFEYBLWMNFZOPB-UHFFFAOYSA-N
SMILES: C=CCCC#N
FDA UNII: 89 HYM37372 · 89HYM37372
EPA Substance Registry System: 4 · 4-Pentenenitrile (592-51-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302+H312+H332
Precautionary statements: 261 · P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn
Risk Statements: 20 · 20/21/22
Safety Statements: 28 · 28-36/37
RIDADR: 3275 · UN 3275 6.1/PG 2
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 2926.9 · 2926.90.5050
HazardClass: 3 · 3/6.1
PackingGroup: II
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
Hazardous Substances Data: 592 · 592-51-8(Hazardous Substances Data)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (95.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 1 item

4-Pentenenitrile is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 4-Pentenenitrile are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Hazards Summary · 1 item

Emergency treatment: Isobutyronitrile; Isobutyronitrile releases cyanide after being absorbed into the body; Causes liver injury in animal studies; [HSDB] Causes respiratory depression and changes to the liver in lethal dose studies of rats; [RTECS] An irritant; [MSDSonline] See NITRILES.

Hazard Classes and CategoriesAcute Tox. 4 (95.3%)

Toxicology

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Toxicity DataLC50 (rat) = 2,550 ppm/4h

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
ridadr: UN 3275 6.1/PG 2
hs_code: 2926.90.5050
risk_code: 20/21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 28-36/37
hazard_class: 3/6.1
Storage Class: 3 - Flammable liquids
packing_group: II
Hazard statements: H302+H312+H332
Hazard Classifications: Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
Precautionary statements: P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
Hazardous Substances Data: 592-51-8(Hazardous Substances Data)

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as an unisolated chemical intermediate in the production of adiponitrile; [HSDB]

UNISOLATED CHEM INT IN PRODN OF ADIPONITRILE

U.S. Exports · 2 items

(1979) No Data

(1981) No Data

U.S. Imports · 2 items

(1979) No Data

(1981) No Data

U.S. Production · 3 items

2023: 8,500,000 - <25,000,000 lb

(1979) NOT ISOLATED COMMERCIALLY IN U.S.

(1981) NOT ISOLATED COMMERCIALLY IN U.S.

Industry UsesIntermediate

Methods of ManufacturingREACTION OF BUTADIENE WITH HYDROGEN CYANIDE PRODUCES A MIXTURE OF 3- & 4-PENTENENITRILE ISOMERS-NO EVIDENCE THAT THE MIXT IS COMMERCIALLY SEPARATED

Applications · 2 items

Uses4-Pentenenitrile may be used to synthesize 4-pentenylamine.

General Description4-Pentenenitrile (4-PN) is a terminal alkene nitrile. It is obtained from 3-pentenenitrile via cationic nickel hydride or cobalt catalyzed isomerization. 4-Pentenenitrile undergoes hydrocyanation in the presence of bidentate nickel complexes (catalysts) to yield 3-pentenenitrile. 4-PN undergoes gas-phase reaction with OH radicals and Cl atoms in the presence of synthetic air and various reference compounds.