Coumarin-6-carboxaldehyde

Base Information

• Chemical Name: Coumarin-6-carboxaldehyde
• CAS No.: 51690-26-7
• Molecular Formula: C10H6O3
• Molecular Weight: 174.156
• Hs Code.: 29322980
• European Community (EC) Number: 674-258-3
• DSSTox Substance ID: DTXSID00370977
• Nikkaji Number: J3.017.563H
• Wikidata: Q72479117
• Mol file: 51690-26-7.mol

Synonyms:Coumarin-6-carboxaldehyde;51690-26-7;2-oxochromene-6-carbaldehyde;2-Oxo-2H-Chromene-6-Carbaldehyde;6-Formaldehydecoumarin;6-Formylcoumarin;6-formyl coumarin;6-Aldehydocoumarin;SCHEMBL971517;DTXSID00370977;2-Oxo-2H-chromene-6-carboxaldehyde;MFCD01941322;AKOS006228794;2-Oxo-2H-1-benzopyran-6-carbaldehyde;PS-6127;CS-0207082;FT-0676481;F14768;A828731;N,N,N,N-TETRAPHENYL-9H-CARBAZOLE-2,7-DIAMINE

Chemical Property of Coumarin-6-carboxaldehyde

Chemical Property:

• Vapor Pressure: 4.51E-06mmHg at 25°C
• Melting Point: 192-194 °C
• Refractive Index: 1.642
• Boiling Point: 383.1 °C at 760 mmHg
• Flash Point: 176 °C
• PSA: 47.28000
• Density: 1.352 g/cm³
• LogP: 1.60550
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 174.031694049
• Heavy Atom Count: 13
• Complexity: 257

Purity/Quality:

98%min ^*data from raw suppliers

Coumarin-6-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=O)O2)C=C1C=O

Technology Process of Coumarin-6-carboxaldehyde

There total 12 articles about Coumarin-6-carboxaldehyde 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%

4-formylphenyl acetate (878-00-2) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → coumarin-6-carboxaldehyde (51690-26-7)

Guidance literature:

With formic acid; rhodium(II) acetate dimer; sodium acetate; In neat (no solvent); at 100 ℃; for 8h; regioselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1021/acs.joc.5b01713

Reference yield: 70.0%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → coumarin-6-carboxaldehyde (51690-26-7)

Guidance literature:

With 1,10-Phenanthroline; copper(II) acetate hydrate; sodium acetate; palladium diacetate; In 1,2-dichloro-ethane; at 110 ℃; for 24h; Molecular sieve;

DOI:10.1002/anie.201305326

Reference yield: 52.0%

chloroform (67-66-3,8013-54-5) + coumarin (91-64-5) → coumarin-6-carboxaldehyde (51690-26-7)

Guidance literature:

coumarin; With potassium hydroxide; In water; for 8h; Reflux;

chloroform; In water; for 4h; pH=Ca. 12; Reflux;

DOI:10.1080/00397911.2010.519847

upstream raw materials:

coumarin

6-hydroxycoumarin

6-methylcoumarin

6-Bromomethyl-coumarin

Downstream raw materials:

2-oxo-2H-benzopyran-6-carboxylic acid

3-(2-isobutoxy-5-(4-isobutoxybenzoyl)phenyl)propionic acid

Refernces

• 1、 Gadakh, Sunita K.,Dey, Soumen,Sudalai, Arumugam. "Rh-Catalyzed Synthesis of Coumarin Derivatives from Phenolic Acetates and Acrylates via C-H Bond Activation". . p. 11544 - 11550. Retrieved 2015/12/04.
• 2、 Sharma, Upendra,Naveen, Togati,Maji, Arun,Manna, Srimanta,Maiti, Debabrata. "Palladium-catalyzed synthesis of benzofurans and coumarins from phenols and olefins". supporting information. p. 12669 - 12673. Retrieved 2013/12/04.