prop-2-enenitrile

• ChemBase ID: 111043
• Molecular Formular: C3H3N
• Molecular Mass: 53.06262
• Monoisotopic Mass: 53.0265491
• SMILES: C=CC#N
• Canonical SMILES: C=CC#N
• InChI: InChI=1S/C3H3N/c1-2-3-4/h2H,1H2
• InChIKey: NLHHRLWOUZZQLW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-enenitrile
• IUPAC Traditional name: acrylonitrile
• Synonyms: cyanoethene; vinylcyanide; POLYACRYLONITRILE; acrylonitrile; Acrylon; Carbacryl; Cyanoethylene; Fumigrain; Propenenitrile; NSC 6362; Acrylonitrile(stabilized with 35-45 ppm 4-hydroxy anisole (H750015)); Vinyl cyanide; Acrylonitrile; 2-Propenenitrile; 乙烯基氰; 丙烯腈

Database IDs

• CAS Number: 25014-41-9; 107-13-1
• EC Number: 203-466-5
• MDL Number: MFCD00001927
• Beilstein Number: 605310
• Merck Index: 14131
• PubChem SID: 24846969; 24869578; 24859251; 162096046
• PubChem CID: 7855
• CHEBI ID: 28217
• CHEMBL: 445612
• Chemspider ID: 7567
• KEGG ID: C01998
• Unique Ingredient Identifier: MP1U0D42PE
• Wikipedia Title: Acrylonitrile

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.7575628
• LogD (pH = 7.4): 0.7575628
• Log P: 0.7575628
• Molar Refractivity: 16.2707 cm^3
• Polarizability: 5.8550863 Å^3
• Polar Surface Area: 23.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 7 g/100 mL at 20 °C in water; Chloroform; ethanol, diethyl ether,; chloroform; Ethyl Acetate
• Apperance: Clear Colourless Oil; Colourless liquid
• Melting Point: -83 °C(lit.); -84 °C(189 K); -84°C
• Boiling Point: 77 °C (350 K); 77 °C(lit.); 77-78°C
• Flash Point: 0°C(32°F); 23 °F; -5 °C
• Auto Ignition Point: 897 °F
• Density: 0.806; 0.806 g/mL at 20 °C; 0.81 g/cm^3; 1.184 g/ml
• Refractive Index: 1.3910; n20/D 1.391; n20/D 1.391(lit.); n20/D 1.392
• Vapor Pressure: 86 mmHg ( 20 °C)
• Vapor Density: 1.83 (vs air)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer
• Storage Warning: Light Sensitive
• RTECS: AT5250000; AT6977900
• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T)
• UN Number: 1093; UN1093
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 1; I
• Risk Statements: 45-11-23/24/25-37/38-41-43-51/53
• Safety Statements: 53-45-61; 53-9-16-45-61; R
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• Main Hazard: flammable,; reactive,; toxic
• NFPA704:
  

  3

  4

  2
• Explode Limits: 17 %
• GHS Hazard statements: H225-H301-H311-H315-H317-H318-H330-H335-H350-H411; H225-H301-H311-H315-H317-H318-H331-H335-H350-H411; H225-H301-H311-H331-H315-H317-H335-H350-H318-H411
• GHS Precautionary statements: P201-P210-P260-P273-P280-P284; P201-P210-P261-P273-P280-P301 + P310; P210-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1093 3/PG 1

Product Information

• Purity: ≥98.0%; ≥99%; ≥99.0%; ≥99.0% (GC); ≥99.5% (GC); 98%; 99+%, stab. with ca 40ppm 4-methoxyphenol
• Grade: analytical standard, for environmental analysis; puriss.; purum; SAJ first grade; SAJ special grade
• Contains: ~0.004% hydroquinone monomethyl ether as stabilizer; 35-45 ppm monomethyl ether hydroquinone as inhibitor
• Quality: stabilized
• Linear Formula: CH2=CHCN

DETAILS

Sigma Aldrich - 320137

Biochem/physiol Actions
An industrial carcinogen that is a multisite carcinogen in rats and possibly carcinogenic to humans.
Packaging
1 L in glass bottle
Application
Acrylonitrile is used in the manufacture of acrylic fibers, resins (acrylonitrile butadiene-styrene, styrene-acrylonitrile and others) and nitrile rubbers (butadiene-acrylonitrile).

Sigma Aldrich - 110213

Biochem/physiol Actions
An industrial carcinogen that is a multisite carcinogen in rats and possibly carcinogenic to humans.
Packaging
1, 2, 4 L in glass bottle
18 L in steel drum
5, 100, 500 mL in glass bottle
Application
Acrylonitrile is used in the manufacture of acrylic fibers, resins (acrylonitrile butadiene-styrene, styrene-acrylonitrile and others) and nitrile rubbers (butadiene-acrylonitrile).

Sigma Aldrich - 01710

Biochem/physiol Actions
An industrial carcinogen that is a multisite carcinogen in rats and possibly carcinogenic to humans.
Application
Acrylonitrile is used in the manufacture of acrylic fibers, resins (acrylonitrile butadiene-styrene, styrene-acrylonitrile and others) and nitrile rubbers (butadiene-acrylonitrile).

Sigma Aldrich - 31564

Biochem/physiol Actions
An industrial carcinogen that is a multisite carcinogen in rats and possibly carcinogenic to humans.
Application
Acrylonitrile is used in the manufacture of acrylic fibers, resins (acrylonitrile butadiene-styrene, styrene-acrylonitrile and others) and nitrile rubbers (butadiene-acrylonitrile).

Sigma Aldrich - 01720

Biochem/physiol Actions
An industrial carcinogen that is a multisite carcinogen in rats and possibly carcinogenic to humans.
Application
Acrylonitrile is used in the manufacture of acrylic fibers, resins (acrylonitrile butadiene-styrene, styrene-acrylonitrile and others) and nitrile rubbers (butadiene-acrylonitrile).

Sigma Aldrich - 01-1350

Biochem/physiol Actions
An industrial carcinogen that is a multisite carcinogen in rats and possibly carcinogenic to humans.
Application
Acrylonitrile is used in the manufacture of acrylic fibers, resins (acrylonitrile butadiene-styrene, styrene-acrylonitrile and others) and nitrile rubbers (butadiene-acrylonitrile).

Sigma Aldrich - 01-1340

Biochem/physiol Actions
An industrial carcinogen that is a multisite carcinogen in rats and possibly carcinogenic to humans.
Application
Acrylonitrile is used in the manufacture of acrylic fibers, resins (acrylonitrile butadiene-styrene, styrene-acrylonitrile and others) and nitrile rubbers (butadiene-acrylonitrile).

REFERENCES

• Free radical alkylation, acylation and arylation reactions also occur in the presence of t-butyl hydroperoxide and a Cu(II) catalyst: J. Chem. Soc., Chem. Commun., 1399 (1995). Several other free radical procedures have been reported involving intramolecular homolytic aromatic substitution to give carbocyclic and heterocyclic systems: Tetrahedron Lett., 36, 4307 (1995):
  
• The Stetter reaction (conjugate addition of aryl aldehydes) catalyzed by CN^-, is exemplified by the addition of pyridine-3-carboxaldehyde to acrylonitrile to give 4-oxo-4-(3-pyridyl)butyronitrile: Org. Synth. Coll., 6, 866 (1988). See also 3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, L08750.
• The reaction is also applicable to acrylate esters and vinyl ketones; with acrylonitrile and phenoxyacetic acid, tetrahydrobenzopyran-4-carbonitrile is obtained in 41% yield.