7,8-Dihydroxy-4-methylcoumarin

Base Information

• Chemical Name: 7,8-Dihydroxy-4-methylcoumarin
• CAS No.: 2107-77-9
• Molecular Formula: C10H8 O4
• Molecular Weight: 192.171
• Hs Code.: 29349990
• European Community (EC) Number: 218-290-4
• NSC Number: 72276,45795
• DSSTox Substance ID: DTXSID30175295
• Nikkaji Number: J67.674H
• Wikidata: Q27185989
• Metabolomics Workbench ID: 74232
• ChEMBL ID: CHEMBL276618
• Mol file: 2107-77-9.mol

Synonyms:7,8-DHMC;7,8-dihydroxy-4-methylcoumarin;DH-methylcoumarin

Chemical Property of 7,8-Dihydroxy-4-methylcoumarin

Chemical Property:

• Vapor Pressure: 1.05E-07mmHg at 25°C
• Melting Point: 242-246 °C(lit.)
• Boiling Point: 421.5°Cat760mmHg
• PKA: 7.72±0.20(Predicted)
• Flash Point: 176°C
• PSA: 70.67000
• Density: 1.456g/cm³
• LogP: 1.51260
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 192.04225873
• Heavy Atom Count: 14
• Complexity: 284

Purity/Quality:

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

7,8-Dihydroxy-4-methyl-2H-chromen-2-one ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2O)O
• Uses: Can be used as a fluorescent sensor to monitor the consumption of a boronic acid in a Suzuki cross-coupling reaction. Use a long wave UV lamp.

Technology Process of 7,8-Dihydroxy-4-methylcoumarin

There total 36 articles about 7,8-Dihydroxy-4-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: 99.0%

acetoacetic acid methyl ester (105-45-3) + 2-hydroxyresorcinol (87-66-1) → 4-methyldaphnetin (2107-77-9)

Guidance literature:

With cobalt(II) supported on mesoporous SBA-15 nanocatalyst; In neat (no solvent); at 100 ℃; for 3h; Green chemistry;

DOI:10.1007/s10562-015-1544-1

Reference yield: 99.0%

Methyl acetoacetate (4525-25-1) + 2-hydroxyresorcinol (87-66-1) → 4-methyldaphnetin (2107-77-9)

Guidance literature:

With boron trifluoride; at 60 ℃; for 0.0833333h;

Reference yield: 80.0%

chloro-trimethyl-silane (75-77-4) + ethyl acetoacetate (141-97-9) + acetic acid (64-19-7,77671-22-8) + 2-hydroxyresorcinol (87-66-1) → 4-methyldaphnetin (2107-77-9)

Guidance literature:

With zinc(II) chloride; at 20 ℃; for 24h;

DOI:10.1007/BF02219707

upstream raw materials:

4-methyleneoxetan-2-one

2-hydroxyresorcinol

8-formyl-4-methyl-7-hydroxycoumarin

ethyl acetoacetate

Downstream raw materials:

7,8-dibenzyloxy-4-methylchromen-2-one

4-methyl-2-oxo-2H-chromene-7,8-diyl dimethanesulfonate

8-hydroxy-4-methyl-7-(toluene-4-sulfonyloxy)-coumarin

8-Hydroxy-7-methoxy-4-methyl-cumarin

Refernces

• 1、 Gangopadhyay, Moumita,Mukhopadhyay, Sourav K.,Karthik,Barman, Shrabani,Pradeep Singh. "Targeted photoresponsive TiO2-coumarin nanoconjugate for efficient combination therapy in MDA-MB-231 breast cancer cells: Synergic effect of photodynamic therapy (PDT) and anticancer drug chlorambucil". . p. 769 - 777. Retrieved 2015.
• 2、 Sharma, Aditi,Tiwari, Meena,Supuran, Claudiu T.. "Novel coumarins and benzocoumarins acting as isoform-selective inhibitors against the tumor-associated carbonic anhydrase IX". . p. 292 - 296. Retrieved 2014.
• 3、 Kumar, Vineet,Tomar, Shilpi,Patel, Ronak,Yousaf, Ahmad,Parmar, Virinder S.,Malhotra, Sanjay V.. "FeCl3-catalyzed Pechmann synthesis of coumarins in ionic liquids". . p. 2646 - 2654. Retrieved 2008.
• 4、 Singh, Prabhjot,Ponnan, Prija,Krishnan, Shibu,Tyagi, Tapesh Kumar,Priya, Nivedita,Bansal, Seema,Scumaci, Domenica,Gaspari, Marco,Cuda, Giovanni,Joshi, Paritosh,Gambhir, Jasvinder Kaur,Saluja, Daman,Prasad, Ashok Kumar,Saso, Luciano,Rastogi, Ramesh Chandra,Parmar, Virinder Singh,Raj, Hanumantharao Guru. "Protein acyltransferase function of purified calreticulin. Part 1: Characterization of propionylation of protein utilizing propoxycoumarin as the propionyl group donor". . p. 625 - 632. Retrieved 2010.
• 5、 Khurana, Pulkit,Kumari, Ranju,Vohra, Parag,Kumar, Ajit,Seema,Gupta, Garima,Raj, Hanumantharao G.,Dwarakanath, Bilikere S.,Parmar, Virinder S.,Saluja, Daman,Bose, Mridula,Vij, Anjana,Chaudhary, Nabo K.,Adhikari, Jawahar S.,Tyagi, Yogesh K.,Kohli, Ekta. "Acetoxy drug: Protein transacetylase catalyzed activation of human platelet nitric oxide synthase by polyphenolic peracetates". . p. 575 - 583. Retrieved 2006.
• 6、 Raj, Hanumantha Rao G.,Parmar, Virinder S.,Jain, Subhash C.,Goel, Sanjay,Tyagi, Yogesh K.,Sharma, Sunil K.,Olsen, Carl E.,Wengel, Jesper. "Mechanism of biochemical action of substituted 4-methylbenzopyran-2- ones. Part 6: Hydrolysis of 7,8-diacetoxy-4-methylcoumarin by a novel deacetylase in rat liver microsomes - A simple method for assay and characterisation". . p. 233 - 237. Retrieved 2000.
• 7、 Yuan, Jingjing,Mohammadnia, Majid. "Preparation of a novel, efficient, and recyclable magnetic catalyst, Cu(II)-OHPC-Fe3O4 nanoparticles, and a solvent-free protocol for the synthesis of coumarin derivatives". . p. 2327 - 2343. Retrieved 2021/07/26.
• 8、 Guerrero, Tomás,Vázquez-Ortega, Fernanda,Lagunes, Irene,Ortiz-Blanco, Erik,Sosa-Ortiz, Gabriela,Tovar-Miranda, Ricardo,Medina, Manuel E.,Trigos, ángel. "Antagonistic activity of hydroxycoumarin-based antioxidants as possible singlet oxygen precursor photosensitizers". . . Retrieved 2021/05/10.