CINNAMONITRILE

Base Information

• Chemical Name: CINNAMONITRILE
• CAS No.: 4360-47-8
• Molecular Formula: C9H7 N
• Molecular Weight: 129.161
• DSSTox Substance ID: DTXSID2052100
• Wikidata: Q204185
• Mol file: 4360-47-8.mol

Synonyms:Cinnamonitrile(6CI,8CI); 1-Cyano-2-phenylethene; 1-Cyano-2-phenylethylene;3-Phenyl-2-propenenitrile; 3-Phenylacrylonitrile; 3-Phenylpropenenitrile; NSC42118; NSC 49137; Styryl cyanide; b-Cyanostyrene; b-Phenylacrylonitrile

Chemical Property of CINNAMONITRILE

Chemical Property:

• Vapor Pressure: 0.0101mmHg at 25°C
• Melting Point: 18-20 ºC
• Refractive Index: n20/D 1.601(lit.)
• Boiling Point: 254-255 ºC
• Flash Point: >230 ºF
• PSA: 23.79000
• Density: 1.028 g/mL at 25 ºC(lit.)
• LogP: 2.22338
• Storage Temp.: Sealed in dry,Room Temperature
• 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:

99.9% ^*data from raw suppliers

Cinnamonitrile 95+% ^*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

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC#N

Technology Process of CINNAMONITRILE

There total 167 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: 100.0%

iodobenzene (591-50-4) + acrylonitrile (107-13-1,25014-41-9) → cinnamonitrile (4360-47-8)

Guidance literature:

With C₃₃H₃₃N₂⁽¹⁺⁾*Cl^(1-); palladium diacetate; potassium carbonate; In water; N,N-dimethyl-formamide; for 2h; Inert atmosphere; Sealed tube; Heating;

DOI:10.13005/ojc/280444

Reference yield: 98.3%

cinnamaldoxime (13372-81-1) → cinnamonitrile (4360-47-8)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; trichlorophosphate; In dichloromethane; at 20 ℃; for 0.75h;

Reference yield: 98.0%

benzaldehyde (100-52-7) + acetonitrile (75-05-8,26809-02-9) → cinnamonitrile (4360-47-8)

Guidance literature:

With P(HNCH₂CH₂)(i-PrNCH₂CH₂)2N; at 50 ℃; for 6h;

DOI:10.1021/jo972343u

upstream raw materials:

methyl magnesium iodide

diethyl ether

cinnamamide

(E)-3-phenylacrylic acid

Downstream raw materials:

Methyl cinnamate

1-Phenylbut-1-en-3-one

3,4-diphenyl-5-oxohexanonitrile

α-n-Propoxy-β-cyano-aethylbenzol

Refernces

• 1、 Arrieta, Ana,Palomo, Claudio. "Reagents and Synthetic Methods; 22. 1-Chlorosulfinyl-4-dimethylaminopyridinium Chloride as a New Reagent for the Dehydration of Aldoximes to Nitriles". . p. 472 - 474. Retrieved 1983.
• 2、 Gibian et al.. "". . p. 640,641, 642. Retrieved 1979.
• 3、 Jiang, Xinglong,Sclafani, Joseph,Prasad, Kapa,Repic, Oljan,Blacklock, Thomas J.. "Pd-smopex-111: A new catalyst for Heck and Suzuki cross-coupling reactions". . p. 769 - 772. Retrieved 2007.
• 4、 Ano, Yusuke,Chatani, Naoto,Higashino, Masaya,Yamada, Yuki. "Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones". supporting information. p. 3799 - 3802. Retrieved 2022/04/07.
• 5、 Jafari, Fariba,Ghorbani-Choghamarani, Arash,Hasanzadeh, Neda. "A new palladium heterogeneous complex (Pd-Gu@BOEH): chemoselective, phosphine-free and practical nanocatalyst in carbon–carbon cross-coupling reaction". . p. 1033 - 1049. Retrieved 2020/11/05.