Cinnamonitrile

Base Information

• Chemical Name: Cinnamonitrile
• CAS No.: 1885-38-7
• Deprecated CAS: 132721-34-7
• Molecular Formula: C9H7N
• Molecular Weight: 129.161
• Hs Code.: 29269095
• European Community (EC) Number: 217-552-5,224-441-5
• NSC Number: 77496,49137,42118
• UNII: H475UV3WWH
• DSSTox Substance ID: DTXSID8044385
• Nikkaji Number: J148.035I,J11.067A
• Wikipedia: Cinnamonitrile
• Wikidata: Q27279623
• ChEMBL ID: CHEMBL2387747
• Mol file: 1885-38-7.mol

Synonyms:2-Propenenitrile,3-phenyl-, (E)-;Cinnamonitrile, (E)- (8CI);(2E)-3-Phenylprop-2-enenitrile;(E)-3-Phenylacrylonitrile;(E)-3-Phenylpropenenitrile;(E)-Cinnamonitrile;NSC77496;trans-3-Phenyl-2-propenenitrile;trans-3-Phenylpropenonitrile;trans-Cinnamonitrile;trans-b-Phenylacrylonitrile;

Chemical Property of Cinnamonitrile

Chemical Property:

• Appearance/Colour: clear colourless to yellow liquid
• Vapor Pressure: 0.0101mmHg at 25°C
• Melting Point: 18-20 °C
• Refractive Index: n20/D 1.601(lit.)
• Boiling Point: 263.8 °C at 760 mmHg
• Flash Point: 105.2 °C
• PSA: 23.79000
• Density: 1.043 g/cm³
• LogP: 2.22338
• Storage Temp.: Store at
• Sensitive.: Air & Light Sensitive
• Solubility.: soluble in Alcohol
• Water Solubility.: insoluble
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 129.057849228
• Heavy Atom Count: 10
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

Cinnamonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC#N
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C#N
• Uses: The parent compound whose derivatives can be applied as corrosion inhibitors for API J55 steel. Cinnamonitrile is a parent compound whose derivatives can be applied as corrosion inhibitors for API J55 steel.

Technology Process of Cinnamonitrile

There total 280 articles about Cinnamonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

dimethylbromosulphonium bromide (50450-21-0) + cinnamaldehyde oxime (59336-59-3) → cinnamic nitrile (1885-38-7) + dimethyl sulfoxide (67-68-5,8070-53-9)

Guidance literature:

In acetonitrile; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2009.07.100

Reference yield: 80.0%

(E)-3-phenylpropenal (14371-10-9) → cinnamic nitrile (1885-38-7) + cinnamamide (621-79-4,22031-64-7)

Guidance literature:

With [Ru(η⁶-C₆Me₆)Cl₂(tris(dimethylamino)phosphine)]; hydroxylamine hydrochloride; sodium hydrogencarbonate; In water; at 100 ℃; for 7h; Reagent/catalyst; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1039/c3ra23195j

Reference yield: 68.0%

iodobenzene (591-50-4) + acrylonitrile (107-13-1,25014-41-9) → cinnamic nitrile (1885-38-7) + (Z)-cinnamonitrile (24840-05-9) + dihydrocinnamonitrile (645-59-0)

Guidance literature:

With potassium carbonate; In water; at 60 - 70 ℃; for 24h; optical yield given as %de; chemoselective reaction;

DOI:10.1002/adsc.200900348

upstream raw materials:

Cinnamyl acetate

1-phenyl-2-propenyl acetate

cinnamyl benzoate

pyridine

Downstream raw materials:

4-phenyl-1H-pyrazole

trans-cinnamic acid tert-pentylamide

3-fluoren-9-yl-3-phenyl-propionitrile

2-methyl-6-phenyl-cyclohex-3-enecarbonitrile

Refernces

• 1、 Kuznetsov,Pan'kova,Ushkov,Selivanov. "Thermolysis of 1-phthalimidoaziridine-2-carbonitriles in the presence of dipolarophiles". . p. 1780 - 1788. Retrieved 2008.
• 2、 Funabiki et al.. "". . p. 1059. Retrieved 1978.
• 3、 Stuhl, Louis S.. "Reaction of 3- with Alkenyl Halides in an Aprotic Medium". . p. 3934 - 3936. Retrieved 1985.
• 4、 Heck, Marie-Pierre,Wagner, Alain,Mioskowski, Charles. "Conversion of primary amides to nitriles by aldehyde-catalyzed water transfer". . p. 6486 - 6487. Retrieved 1996.
• 5、 Bozell, Joseph J.,Voght, Charles E.. "Bimetallic Catalysis. A New Method for the Activation of Chloroarenes toward Palladium-Catalyzed Coupling with Olefins". . p. 2655 - 2657. Retrieved 1988.
• 6、 Cwik, Agnieszka,Hell, Zoltan,Figueras, Francois. "Palladium/magnesium-lanthanum mixed oxide catalyst in the heck reaction". . p. 523 - 530. Retrieved 2006.
• 7、 Haruta, Ryuichi,Ishiguro, Masaharu,Furuta, Kyoji,Mori, Atsunori,Ikeda, Nobuo,Yamamoto, Hisashi. "STEREOSELECTIVE CARBONYL OLEFINATION VIA ORGANOSILICON COMPOUNDS. BORON AND TITANIUM REAGENTS". . p. 1093 - 1096. Retrieved 1982.
• 8、 Clegg, William,Elsegood, Mark R. J.,Jackson, Richard F. W.,Fraser, Joanne L.,Emsden, Lee J.. "N-(2,3,5,6-tetrachloropyrid-4-yl)cinnamide". . p. 797 - 799. Retrieved 1997.
• 9、 Wood et al.. "-". . p. 4907,4908,4910. Retrieved 1979.
• 10、 -. "Method for dehydrating primary amide into nitriles under catalysis of cobalt". Paragraph 0090-0092. . Retrieved 2021/06/21.