Ferulamide

Base Information

• Chemical Name: Ferulamide
• CAS No.: 19272-90-3
• Molecular Formula: C10H11NO3
• Molecular Weight: 193.202
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID201031242
• Nikkaji Number: J1.716.286A,J1.736.594K
• Wikidata: Q76325452
• Mol file: 19272-90-3.mol

Synonyms:Ferulamide;61012-31-5;3-(4-hydroxy-3-methoxyphenyl)acrylamide;4-Hydroxy-3-methoxycinnamide;19272-90-3;Ferulic amide;Ferulamid;Ferulic acid amide;3-(4-Hydroxy-3-methoxyphenyl)-2-propenamide;(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide;CINNAMAMIDE, 4-HYDROXY-3-METHOXY-;2-Propenamide, 3-(4-hydroxy-3-methoxyphenyl)-;(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenamide;2-Propenamide, 3-(4-hydroxy-3-methoxyphenyl)-, (E)-;3-Methoxy-4-hydroxycinnamamide;DTXSID201031242;HY-N3894;AKOS006243234;LS-53980;CS-0024415;(E)-3-(4-hydroxy-3-methoxyphenyl)acrylamide;A868837;AN-068/14539047;NCGC00381167-01!(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide

Chemical Property of Ferulamide

Chemical Property:

• Vapor Pressure: 3.48E-08mmHg at 25°C
• Refractive Index: 1.624
• Boiling Point: 435.3 °C at 760 mmHg
• Flash Point: 217 °C
• PSA: 73.54000
• Density: 1.257 g/cm³
• LogP: 2.04900
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 193.07389321
• Heavy Atom Count: 14
• Complexity: 227

Purity/Quality:

>98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)N)O
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)N)O

Technology Process of Ferulamide

There total 9 articles about Ferulamide 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: 69.0%

C12H13NO4 → 3-(4-hydroxy-3-methoxyphenyl)acrylamide (19272-90-3)

Guidance literature:

With methanol; sodium methylate; at 0 ℃; for 0.25h;

DOI:10.1002/ardp.201500317

Reference yield:

3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) → 3-(4-hydroxy-3-methoxyphenyl)acrylamide (19272-90-3)

Guidance literature:

Multi-step reaction with 4 steps

1: dmap / 0 - 10 °C

2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 0 °C

3: ammonium hydroxide; water / dichloromethane / 0 °C

4: sodium methylate; methanol / 0.25 h / 0 °C

With methanol; dmap; ammonium hydroxide; oxalyl dichloride; water; sodium methylate; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1002/ardp.201500317

Reference yield:

3-(4-acetoxy-3-methoxyphenyl)prop-2-enoic acid (34749-55-8,147677-05-2,2596-47-6) → 3-(4-hydroxy-3-methoxyphenyl)acrylamide (19272-90-3)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 0 °C

2: ammonium hydroxide; water / dichloromethane / 0 °C

3: sodium methylate; methanol / 0.25 h / 0 °C

With methanol; ammonium hydroxide; oxalyl dichloride; water; sodium methylate; N,N-dimethyl-formamide; In dichloromethane;

DOI:10.1002/ardp.201500317

upstream raw materials:

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

3-(4-acetoxy-3-methoxyphenyl)prop-2-enoic acid

4-acetoxyferuloyl chloride

vanillin

Refernces

• 1、 Badavath, Vishnu N.,Baysal, Ipek,Uar, Gülberk,Mondal, Susanta K.,Sinha, Barij N.,Jayaprakash, Venkatesan. "Monoamine Oxidase Inhibitory Activity of Ferulic Acid Amides: Curcumin-Based Design and Synthesis". . p. 9 - 19. Retrieved 2016/01/29.