4-HYDROXY-6-METHYLCOUMARIN

Base Information

• Chemical Name: 4-HYDROXY-6-METHYLCOUMARIN
• CAS No.: 13252-83-0
• Molecular Formula: C10H8 O3
• Molecular Weight: 176.172
• Hs Code.: 29322985
• Mol file: 13252-83-0.mol

Synonyms:Coumarin,4-hydroxy-6-methyl- (7CI,8CI); 4-Hydroxy-6-methyl-2H-1-benzopyran-2-one;4-Hydroxy-6-methyl-2H-chromen-2-one; 4-Hydroxy-6-methylcoumarin;6-Methyl-4-hydroxycoumarin

Chemical Property of 4-HYDROXY-6-METHYLCOUMARIN

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 261-264 °C(lit.)
• Boiling Point: 314.4°Cat760mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 128.7°C
• PSA: 50.44000
• Density: 1.372g/cm³
• LogP: 1.80700
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

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

4-Hydroxy-6-methyl-2H-chromen-2-one ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: 4-Hydroxy-6-methylcoumarin may be used for the in situ generation of α-methylenechromanes, α-methylenequinoline and ortho-quinone methides, via Knoevenagel reaction. It may be used for the preparation of 8-methyl-2-phenyl-4H-furo-[3,2-c]benzopyran-4-one and 6-methyl-2-phenyl-4H-furo-[2,3-b]benzopyran-4-one.

Technology Process of 4-HYDROXY-6-METHYLCOUMARIN

There total 16 articles about 4-HYDROXY-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: 92.0%

5-methyl-2-hydroxyacetophenone (1450-72-2) + Diethyl carbonate (105-58-8,76619-83-5) → 4-hydroxy-6-methylcoumarin (13252-83-0)

Guidance literature:

With sodium hydride; In mineral oil; at 0 - 100 ℃;

DOI:10.1021/jm9011609

Reference yield: 92.0%

5-methyl-2-hydroxyacetophenone (1450-72-2) + carbon monoxide (201230-82-2) → 4-hydroxy-6-methylcoumarin (13252-83-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 80 ℃; for 4h; under 7355.08 Torr;

DOI:10.1055/s-1988-27537

Reference yield: 71.0%

2-trichloromethyl-6-methylchromone (152894-72-9) → 4-hydroxy-6-methylcoumarin (13252-83-0)

Guidance literature:

With potassium hydroxide; In methanol; for 0.5h; Heating;

DOI:10.1007/BF02494778

upstream raw materials:

6-methyl-chromen-4-one

5-methyl-2-hydroxyacetophenone

carbon monoxide

aluminium trichloride

Downstream raw materials:

SKI-190986

5-methyl-2-hydroxyacetophenone

7,10-dihydroxy-9-methoxy-6-(4-methoxyphenyl)-3-methyl-6H,11H-<2>benzopyrano<4,3-c><1>benzopyran-11-one

5-(2-Hydroxy-5-methyl-phenyl)-2-methyl-2,4-dihydro-pyrazol-3-one

Refernces

• 1、 Chen, Zhi-Wei,Hou, Jun-Bo,Dai, Zhao-Ran,Yang, Xiao-Feng. "A regioselective synthesis of pentacyclic compounds containing coumarin, pyrrole, indene without catalysts under microwave irradiation". . p. 1622 - 1625. Retrieved 2016.
• 2、 Feng, Xi,Qin, Zhen,Cheng, Xinying,Liu, Dongyu,Peng, Yinghe,Huang, Huidan,Song, Bin,Bian, Jinlei,Li, Zhiyu. "Copper(II)-Catalyzed Tandem Reaction: Synthesis of Furo[3,2- c]coumarin Derivatives and Evaluation for Photophysical Properties". supporting information. p. 12537 - 12548. Retrieved 2021/09/20.
• 3、 Hoppe, Heinrich C.,Isaacs, Michelle,Kaye, Perry T.,Krause, Rui W. M.,Manyeruke, Meloddy H.,Seldon, Ronnett,Tshiwawa, Thendamudzimu,Warner, Digby F.. "Synthesis and biological evaluation of bis-N2,N2′-(4-hydroxycoumarin-3-yl)ethylidene]-2,3-dihydroxysuccinodihydrazides". . . Retrieved 2020/01/22.