3-Chloro-4-methyl-7-hydroxycoumarin

Base Information

• Chemical Name: 3-Chloro-4-methyl-7-hydroxycoumarin
• CAS No.: 6174-86-3
• Deprecated CAS: 119739-80-9
• Molecular Formula: C10H7 Cl O3
• Molecular Weight: 210.617
• Hs Code.: 2932209090
• European Community (EC) Number: 228-217-8
• NSC Number: 44204,24924
• UNII: EVI89HA9V3
• DSSTox Substance ID: DTXSID8052724
• Nikkaji Number: J211.437B
• Wikidata: Q27117921
• Pharos Ligand ID: 5HZP9NDK41U8
• Metabolomics Workbench ID: 55938
• ChEMBL ID: CHEMBL589883
• Mol file: 6174-86-3.mol

Synonyms:3-chloro-4-methyl-7-hydroxycoumarin;chlorferon;chlorferron

Chemical Property of 3-Chloro-4-methyl-7-hydroxycoumarin

Chemical Property:

• Vapor Pressure: 3.63E-07mmHg at 25°C
• Melting Point: 240-244 °C(lit.)
• Boiling Point: 405.8°C at 760 mmHg
• PKA: 7.43±0.20(Predicted)
• Flash Point: 199.2°C
• PSA: 50.44000
• Density: 1.48g/cm³
• LogP: 2.46040
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 210.0083718
• Heavy Atom Count: 14
• Complexity: 298

Purity/Quality:

99% ^*data from raw suppliers

Chlorferon-13C6 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=O)OC2=C1C=CC(=C2)O)Cl
• Uses: Labelled Chlorferon is has α-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives. Also used in the synthesis of fluorogenic substrates for the detection of bacterial β-Galactosidase.

Technology Process of 3-Chloro-4-methyl-7-hydroxycoumarin

There total 9 articles about 3-Chloro-4-methyl-7-hydroxycoumarin 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%

ethyl 2-chloro-3-oxo-butyrate (609-15-4) + recorcinol (108-46-3) → 3-chloro-4-methylumbelliferone (6174-86-3)

Guidance literature:

With trifluoroacetic acid; at 100 ℃; for 0.5h; regioselective reaction; Microwave irradiation;

DOI:10.1002/chem.201201039

Reference yield: 96.0%

methyl 2-chloroacetoacetate (4755-81-1,935731-92-3) + recorcinol (108-46-3) → 3-chloro-4-methylumbelliferone (6174-86-3)

Guidance literature:

With aluminum oxide; methanesulfonic acid; at 20 ℃; for 0.133333h;

DOI:10.1016/S0385-5414(07)81208-1

Reference yield: 83.5%

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) → 3-chloro-4-methylumbelliferone (6174-86-3)

Guidance literature:

With N-chloro-succinimide; copper(II) chloride monohydrate; zinc(II) chloride; In acetonitrile; at 82 ℃; for 0.05h; regioselective reaction;

DOI:10.1055/s-0037-1612080

upstream raw materials:

7-hydroxy-4-methyl-chromen-2-one

3-chloro-4-methyl-2-oxo-2H-chromen-7-ylacetate

ethyl 2-chloro-3-oxo-butyrate

recorcinol

Downstream raw materials:

3-chloro-7-dimethoxythiophosphoryloxy-4-methyl-coumarin

coumaphos

3-chloro-4-methyl-7-propionyloxy-coumarin

3-Chloro-7-methoxy-4-methylcoumarin

Refernces

• 1、 Fernández-Bola?os, José G.,Fernandes, Miguel X.,Fuentes-Aguilar, Alma,López, óscar,Merino-Montiel, Penélope,Meza-Reyes, Socorro,Montiel-Smith, Sara,Nocentini, Alessio,Padrón, José M.,Petreni, Andrea,Puerta, Adrián,Supuran, Claudiu T.,Vega-Báez, José Luis. "2-Aminobenzoxazole-appended coumarins as potent and selective inhibitors of tumour-associated carbonic anhydrases". . p. 168 - 177. Retrieved 2021/12/21.
• 2、 Yu, Haonan,Hou, Zhuang,Tian, Ye,Mou, Yanhua,Guo, Chun. "Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents". . p. 434 - 449. Retrieved 2018/04/14.