Cinnamamide

Base Information

• Chemical Name: Cinnamamide
• CAS No.: 22031-64-7
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.177
• European Community (EC) Number: 210-707-8,679-596-5
• UNII: Y0JET56H7N
• DSSTox Substance ID: DTXSID4060739,DTXSID901035045
• Nikkaji Number: J29.512D,J75.156A
• NSC Number: 244944,32953
• Wikidata: Q63390539
• Mol file: 22031-64-7.mol

Synonyms:cinnamamide

Chemical Property of Cinnamamide

Chemical Property:

• Vapor Pressure: 4.44E-05mmHg at 25°C
• Melting Point: 148-150 °C(lit.)
• Refractive Index: 1.613
• Boiling Point: 350.3 °C at 760 mmHg
• PKA: 15?+-.0.50(Predicted)
• Flash Point: 165.6 °C
• PSA: 43.09000
• Density: 1.121 g/cm³
• LogP: 1.88540
• Storage Temp.: 2-8°C
• Solubility.: almost transparency in Methanol
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-Cinnamamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC(=O)N
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C(=O)N
• Uses: trans-Cinnamamide is used in the used in the synthesis of U-77863 and U-77864 as it has antitumor activity.

Technology Process of Cinnamamide

There total 121 articles about Cinnamamide 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%

Cinnamoyl chloride (102-92-1,17082-09-6) → cinnamamide (621-79-4,22031-64-7)

Guidance literature:

With ammonium hydroxide; In tert-butyl methyl ether; at 0 - 20 ℃;

DOI:10.1002/adsc.202100198

Reference yield: 100.0%

cinnamic nitrile (1885-38-7) → cinnamamide (621-79-4,22031-64-7)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; dimethyl sulfoxide; In methanol; water; at 50 ℃; for 1h;

DOI:10.1246/bcsj.54.793

Reference yield: 99.3%

iodobenzene (591-50-4) + 2-propenamide (79-06-1,12624-24-7,25038-45-3,27754-57-0,33338-03-3,39387-77-4,68247-81-4,9082-06-8,79079-15-5) → cinnamamide (621-79-4,22031-64-7)

Guidance literature:

With triethylamine; {[Pd(η⁵-C5H5)Fe(η⁵-C5H3)C(CH3)=N(C6H4CH3-4)](μ-I)}2; In 1,4-dioxane; at 100 ℃; for 15h;

DOI:10.1016/S0022-328X(01)00967-6

upstream raw materials:

acetamide

ethyl 3-phenyl-2-propenoate

diethyl ether

cinnamic nitrile

Downstream raw materials:

cinnamonitrile

2,6-dioxo-4-phenyl-piperidine-3-carbonitrile

2,6-dioxo-4-phenyl-piperidine-3-carboxylic acid ethyl ester

2,3-dibromo-3-phenyl-propionic acid amide

Refernces

• 1、 Yilmaz, Mehmet,Ustalar, Ash,U?an, Bedriye,Pekel, A. Tar?k. "Regio- and diastereoselective synthesis of trans-dihydrofuran-3carboxamides by radical addition of 1,3-dicarbonyl compounds to acrylamides using manganese(III) acetate and determination of exact configuration by X-ray crystallography". . p. 79 - 91. Retrieved 2016.
• 2、 Petrova, Jordanka,Momchilova, Snezhana,Vassilev, Nikolay G.. "The HWE reaction in solid - liquid two phase system for the synthesis of α,β-unsaturated amides". . p. 87 - 94. Retrieved 2000.
• 3、 Chattopadhyaya,Rao. "-". . p. 2899. Retrieved 1974.
• 4、 Grams, R. Justin,Lawal, Monsurat M.,Szwetkowski, Connor,Foster, Daniel,Rosenblum, Carol Ann,Slebodnick, Carla,Welborn, Valerie Vaissier,Santos, Webster L.. "Organocatalytic Trans Semireduction of Primary and Secondary Propiolamides: Substrate Scope and Mechanistic Studies". supporting information. p. 172 - 178. Retrieved 2021/10/14.
• 5、 Huang, Zijun,Jiang, Xiongwei,Lan, Donghui,Li, Yuehui,Pi, Shaofeng,Tan, Zhengde,Tang, Jia,Xie, Tianle,Yi, Bing,Zhang, Minmin. "Iron-catalyzed hydroaminocarbonylation of alkynes: Selective and efficient synthesis of primary α,β-unsaturated amides". supporting information. . Retrieved 2022/02/22.