Isobutyronitrile

HCID 6559CAS 78-82-0

Grundinformationen

Standard-SMILES
CC(C)C#N
InChIKey
LRDFRRGEGBBSRN-UHFFFAOYSA-N
Summenformel
C4H7N
Durchschnittliche Molmasse
69,11 g/mol
Monoisotopische Masse
69,05784922

Überblick

Isobutyronitrile appears as a clear colorless liquid. Flash point 47 °F. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.

Namen und Bezeichner

Bevorzugter Name
Isobutyronitrile
IUPAC
2-methylpropanenitrile
Lokaler Name
Isobutyronitril
Englischer Name
Isobutyronitrile
Summenformel
C4H7N
Molmasse
69.11

Namen und Synonyme

Isobutyronitrile2-METHYLPROPANENITRILE78-82-0Isopropyl cyanide2-MethylpropionitrilePropanenitrile, 2-methyl-Dimethylacetonitrile2-CyanopropaneIsopropyl nitrileIsopropylnitrile1-Cyano-1-methylethaneIsopropylkyanid
Weitere Namen anzeigen
isiobutyronitrileAzobis (2-methylpropionitrile)iso-C3H7CNIsobutyronitrilIsopropylcyanid
2-Methylpropane nitrilealpha-MethylpropanenitrileDTXSID5026461ISOBUTANENITRILEUN2284Propanoic acid, 2-methyl-, nitrile699AWF2WV2NSC-60536

Datenbank-Bezeichner

CAS
78-82-0
PubChem CID
6559
DTXSID
DTXSID5026461
ChEMBL
CHEMBL1492874
ChEBI
CHEBI:28638
UNII
699AWF2WV2
EC Number
201-147-5
Nikkaji
J1.959C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,5
Polarare Oberfläche (TPSA)
23,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
5

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Nitrogen Compounds -> Nitriles

Flammable agents - 3rd degree

SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogPlog Kow = 0.46
OdorAlmond-like odor
Density · 4 Einträge

0.733 to 0.7608 at 68 to 86 °F (EPA, 1998)

0.7704 g/cu cm at 20 °C

0.7704 @ 20°C

0.76

Viscosity0.551 cP at 15 °C; 0.456 cP at 30 °C

Physikochemische Eigenschaften

Schmelzpunkt
-72 °C · -72 °C (lit.)
Siedepunkt
107 · 107-108 °C (lit.)
Dichte
0.77 g/mL · 0.770 g/mL at 20 °C (lit.)
Dampfdichte
2.38 · 2.38 (vs air)
Dampfdruck
100 mm · 100 mm Hg ( 54.4 °C)
Brechungsindex
20 · n20/D 1.372(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H225 (87.1%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 210 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Propanenitrile, 2-methyl-

Propanenitrile, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanenitrile, 2-methyl- 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)

Status: Active Update: 12-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/19480

Propanenitrile, 2-methyl-: HSNO Approval: HSR001175 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid Poison
Fire Hazards · 2 Einträge

Vapor may explode if ignited in an enclosed area. Toxic oxides of nitrogen are produced during combustion. It 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. (EPA, 1998)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Fire PotentialA very dangerous fire hazard when exposed to heat or flame.
Health Hazards · 2 Einträge

Poisonous; 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. (EPA, 1998)

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

Hazards SummaryIsobutyronitrile is hazardous by the oral, skin, or inhalation routes; it causes liver injury in animal feeding studies. Animals inhaling 5500 ppm for one hour have convulsions and die. [HSDB] See NITRILES.

Sicherheit und Schutzausrüstung

Fire Fighting · 1 Eintrag

Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear positive pressure breathing apparatus and special protective clothing. Isolate for 1/2 mile in all directions if tank car or truck is involved in fire. Move container from fire area if you can do so without risk. Dike fire control water for later disposal; do not scatter the material. Spray cooling water on containers that are exposed to flames until well after fire is out. Withdraw immediately in case of rising sound from venting safety device or any discoloration of tank due to fire.

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 Einträge

Warning: Heart palpitation may occur within minutes after exposure. High doses can stop breathing. Vital signs should be monitored closely. Caution is advised.

General First Aid:

(General first aid procedures)

Firefighting Hazards · 1 Eintrag

Vapor explosion and poison hazard indoors, outdoors, or in sewers. Runoff to sewer may create fire or explosion hazard. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions.

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 5 Einträge

Suitable extinguishing media: For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Use water spray to cool unopened containers.

Extinguish with dry chemical, carbon dioxide, water spray, foam, or fog. Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear positive pressure breathing apparatus and special protective clothing. Isolate for 1/2 mile in all directions if tank car or truck is involved in fire. Move container from fire area if you can do so without risk. Dike fire control water for later disposal; do not scatter the material. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. ... The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.

Toxikologische Informationen

Target OrgansEyes, skin, respiratory system, central nervous system, cardiovascular system
Ecotoxicity Values · 2 Einträge

EC50; Species: Pseudokirchneriella subcapitata (Green Algae) 15000 cells/mL; Conditions: freshwater, static, 24 °C; Concentration: 728500 ug/L for 48 hr; Effect: decreased population growth rate

EC50; Species: Pimephales promelas (Fathead Minnow) cell line derived from tissue posterior to anus; Conditions: freshwater, in vitro, 34 °C; Concentration: 37200000 ug/L for 24 hr; Effect: cell biochemistry, decreased protein content

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a log Kow of 0.46(2) and a regression-derived equation(3), indicates that 2-methylpropanenitrile is expected to have very high mobility in soil(SRC). Volatilization of 2-methylpropanenitrile from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.4X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 2-Methylpropanenitrile is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 32.7 mm Hg at 25 °C(5). A 53.9% of theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 37(SRC), determined from a log Kow of 0.46(2) and a regression-derived equation(3), indicates that 2-methylpropanenitrile is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 5.4X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 16 hours and 7 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 53.9% of theoretical BOD using activated sludge in the Japanese MITI test(7) suggests that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-methylpropanenitrile which has a vapor pressure of 32.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-methylpropanenitrile is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 15 days(SRC), calculated from its rate constant of 7.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Methylpropanenitrile does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

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.
Exposure Routesinhalation, skin absorption, ingestion, skin and/or eye contact
Toxicity Summary · 1 Eintrag

IDENTIFICATION AND USE: 2-Methylpropanenitrile is a colorless liquid. It is used as intermediate for insecticides, solvent, as a catalyst in the polymerization of ethylene. HUMAN STUDIES: Potential symptoms of overexposure are irritation of eyes, skin, nose, throat; headache, dizziness, weakness, giddiness, confusion, convulsions, dyspnea, abdominal pain, nausea, vomiting. Cases of inhalation exposure included loss of consciousnesses, tonic-clonic movements of the arms, dilated pupils, weak pulse, shallow and gasping breathing, and cyanosis. ANIMAL STUDIES: Local effects in rabbit's eyes included reddening of eyelids and conjunctiva, edema, and tearing. Vapor inhalation at a calculated concentration of 5500 ppm for approximately 1 hr killed all rats. In rats and mice exposed orally the symptoms were those of weakness, vasodilation, tremors, and convulsions. Thiocyanate was present in the urine. Rats exposed at 38.6 mg/kg orally showed definite parenchymatous degeneration of the liver, with male rats showing a greater degree of degeneration than females. Increased weight of stomach, liver, and adrenal glands were found at doses of 200 mg/kg orally. It was concluded that 2-methylpropanenitrile causes hepatic damage. In rabbits the direct cause of death after iv administration was respiratory arrest from depression of the central mechanism of ventilation control. The mice showed central nervous system signs such as respiratory paralysis, slight hyperkinesia, increase in frequency and amplitude of respiration, clonic movements of limbs, diminution of pain sensitivity, and decreased frequency in respiration with cessation and death at 20-30 min after injection.

Regulatorische Informationen

CERCLA Reportable Quantities · 1 Eintrag

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Isobutyronitrile is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1000 lbs.

DHS Chemicals of Interest (COI) · 4 Einträge

Isobutyronitrile

1

20000

Toxic chemical that can be released at a facility.

Sicherheitsdaten

OEB
A
OEL
TWA: 8 ppm (22 mg/m3)
wgk
2
tsca
TSCA listed
ridadr
UN 2284
hs_code
29269095

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

1. A method for determination of cyanide release during microsomal metabolism of organonitriles was developed. 2. Vmax values for cyanide release from acetonitrile, propionitrile, butyronitrile, isobutyronitrile, acrylonitrile, benzyl cyanide and succinonitrile were determined for rat nasal and liver microsomal metabolism. 3. Km and Vmax values were determined for nasal and liver microsomal metabolism of benzyl cyanide to cyanide. 4. Vmax values were all greater in nasal microsomes than in liver microsomes. Except for acrylonitrile, butyronitrile and isobutyronitrile metabolism, the ethmoturbinate microsomes had higher activities than the maxilloturbinate microsomes. 5. Two methods for determining Vmax values indicate that rat liver, but not the nose, contains at least two cytochrome P-450 isozymes involved in metabolism of benzyl cyanide to cyanide. 6. These results, and previously reported nasal rhodanese activity data, indicate that inhaled organonitriles are substantially detoxicated in the nasal cavity.

... The oral LD50 in rats /was found/ to be 50-100 mg/kg and in mice, 5-10 mg/kg. ... Thiocyanate was present in the urine.

Verwendung und Herstellung

Uses · 6 Einträge

Used in the synthesis of insecticides and gasoline additives; used as a catalyst in the production of polyethylene; [HSDB]

Intermediate for insecticides, etc.

Solvent

Isobutyronitrile ... is used in organic synthesis and as a gasoline additive

As a catalyst in the polymerization of ethylene.

Its major use is the synthesis of the insecticide diazinon.

U.S. Production · 2 Einträge

2023: 550,000 - <1,000,000 lb

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2-Methylpropanenitrile:

Industry UsesNot Known or Reasonably Ascertainable
Methods of ManufacturingIsobutyronitrile is usually obtained by the catalytic gas-phase reaction of isobutyraldehyde or isobutanol with ammonia.
General Manufacturing Information · 2 Einträge

All Other Basic Organic Chemical Manufacturing

Propanenitrile, 2-methyl-: ACTIVE

Anwendungen · 1 Eintrag

VerwendenIsobutyronitrile 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.

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