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107-13-1 - Acrylonitrile, 99+%, stab. with ca 40ppm 4-methoxyphenol - Propenenitrile - Vinyl cyanide - A13058 - Alfa Aesar

A13058 Acrylonitrile, 99+%, stab. with ca 40ppm 4-methoxyphenol

CAS Number
107-13-1
Synonyms
Propenenitrile
Vinyl cyanide

Size Price ($) Quantity Availability
100ml 13.41
500ml 20.97
2500ml 63.00
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Acrylonitrile, 99+%, stab. with ca 40ppm 4-methoxyphenol

MDL
MFCD00001927
EINECS
203-466-5

Chemical Properties

Formula
C3H3N
Formula Weight
53.06
Melting point
-84°
Boiling Point
77-78°
Flash Point
0°(32°F)
Density
0.806
Refractive Index
1.3910
Sensitivity
Light Sensitive
Solubility
Miscible with isopropanol, ethanol, ether, acetone, water, carbon tetrachloride, ethyl acetate, toluene and benzene.

Applications

Acrylonitrile acts as a monomer used in the production of polyacrlonitrile plastics, adhesives and synthetic rubber. It is also used for the synthesis of copolymers such as styrene-acrylonitrile, acrylonitrile butadiene styrene, acrylonitrile styrene acrylate. It is involved in the preparation of adiponitrile by dimerization, which finds application in polyamide synthesis. It acts as a precursor to acrylamide and acrylic acid. It is used as dienophile in Diels-Alder reactions. It acts as a chemical intermediate in the synthesis of antioxidants, active pharmaceutical ingredients, dyes, and surface-active agents. Further, it is utilized for the preparation of acrylic fibers, resins and nitrile rubbers. In addition to this, it serves as a fumigant for food commodities, flour milling, and bakery food processing equipment.

Notes

Light sensitive. Incompatible with oxidizing agents, acids, alkalis, metals, bromine, peroxides and copper.

Literature References

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.

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 reaction is also applicable to acrylate esters and vinyl ketones; with acrylonitrile and phenoxyacetic acid, tetrahydrobenzopyran-4-carbonitrile is obtained in 41% yield.

Dai, Y.; Song, Y.; Tu, X.; Jiang, Y.; Yuan, Y. Sequential shape-selective adsorption and photocatalytic transformation of acrylonitrile production wastewater. Water Res. 2015, 85, 216-225.

Pan, X.; Lamson, M.; Yan, J.; Matyjaszewski, K. Photoinduced Metal-Free Atom Transfer Radical Polymerization of Acrylonitrile. ACS Macro Lett. 2015, 4 (2), 192-196.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H301-H311-H331-H315-H317-H335-H350-H318-H411

Highly flammable liquid and vapour. Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Causes skin irritation. May cause an allergic skin reaction. May cause respiratory irritation. May cause cancer. Causes serious eye damage. Toxic to aquatic life with long lasting effects.

Precautionary Statements: P210-P201-P261-P273-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,131
Beilstein
605310
Hazard Class
3
Packing Group
I
Harmonized Tariff Code
2926.10
TSCA
Yes
RTECS
AT5250000

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