6-Methylcoumarin

Base Information

• Chemical Name: 6-Methylcoumarin
• CAS No.: 92-48-8
• Molecular Formula: C10H8O2
• Molecular Weight: 160.172
• Hs Code.: 29321900
• European Community (EC) Number: 202-158-8
• NSC Number: 5870
• UNII: EHP8W0L01A
• DSSTox Substance ID: DTXSID9025588
• Nikkaji Number: J3.219K
• Wikidata: Q245490
• Metabolomics Workbench ID: 45484
• ChEMBL ID: CHEMBL443436
• Mol file: 92-48-8.mol

Synonyms:Coumarin,6-methyl- (6CI,7CI,8CI);6-MC;6-Methyl-2H-1-benzopyran-2-one;6-Methyl-2H-chromen-2-one;6-Methylbenzopyrone;6-Methylcoumarinic anhydride;NSC 5870;Toncarine;

Chemical Property of 6-Methylcoumarin

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Melting Point: 75-76 °C
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 304.6 °C at 760 mmHg
• Flash Point: 124.3 °C
• PSA: 30.21000
• Density: 1.2 g/cm³
• LogP: 2.10140
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 160.052429494
• Heavy Atom Count: 12
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

6-Methylcoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-42/43
• Safety Statements: 22-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CC1=CC2=C(C=C1)OC(=O)C=C2
• Uses: 6-Methylcoumarin is a synthetic fragrance in cosmetics, toiletries and soaps. It mainly used to prepare flavors such as coconut, vanilla and caramel.

Technology Process of 6-Methylcoumarin

There total 51 articles about 6-Methylcoumarin 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%

4-methylphenyl propynoate (110450-40-3) → 6-methylcoumarin (92-48-8)

Guidance literature:

With Echavarren's catalyst; In dichloromethane; at 18 ℃; for 1h;

DOI:10.1021/acs.joc.0c02011

Reference yield: 95.0%

2-hydroxy-5-methylbenzaldehyde (613-84-3) + S-phenyl hydrogen thiomalonate (4279-77-0) → 6-methylcoumarin (92-48-8)

Guidance literature:

With triethylamine; benzylamine; In chloroform; at 55 ℃; for 9h;

DOI:10.1002/ejoc.201300538

Reference yield: 94.0%

(E)-ethyl 3-(2-hydroxy-5-methylphenyl)acrylate (175647-90-2) → 6-methylcoumarin (92-48-8)

Guidance literature:

With tris[2-phenylpyridinato-C₂,N]iridium(III); In acetonitrile; at 20 ℃; for 24h; Sealed tube; Inert atmosphere; Irradiation;

upstream raw materials:

6-bromo-2H-chromen-2-one

methyl iodide

p-cresol

malic acid

Downstream raw materials:

6-methyl-4-phenylsulfanyl-chroman-2-one

6-methyl-4-p-tolylmercapto-chroman-2-one

4-benzylmercapto-6-methyl-chroman-2-one

6-methyl-4-o-tolylmercapto-chroman-2-one

Refernces

• 1、 Mustafa et al.. "-". . p. 888,889. Retrieved 1957.
• 2、 Chen, Zhiwei,Bai, Xiang,Sun, Jie,Xu, Yicheng. "Fe(III)-Catalyzed Decarboxylative C3-Difluoroarylmethylation of Coumarins with α,α-Difluoroarylacetic Acids". supporting information. p. 7674 - 7682. Retrieved 2020/07/15.
• 3、 Jin, Can,Sun, Bin,Xu, Tengwei,Yan, Zhiyang,Zhang, Xun. "Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides". supporting information. p. 1585 - 1591. Retrieved 2019/08/07.