5,7-Dihydroxy-4-methylcoumarin

Base Information

• Chemical Name: 5,7-Dihydroxy-4-methylcoumarin
• CAS No.: 2107-76-8
• Molecular Formula: C10H8O4
• Molecular Weight: 192.171
• Hs Code.: 29321900
• European Community (EC) Number: 218-289-9
• NSC Number: 5302
• UNII: VP62D4346M
• DSSTox Substance ID: DTXSID0025078
• Nikkaji Number: J298.698A
• Wikidata: Q27291948
• Metabolomics Workbench ID: 74230
• ChEMBL ID: CHEMBL12252
• Mol file: 2107-76-8.mol

Synonyms:5,7-DHMC;5,7-dihydroxy-4-methylcoumarin

Chemical Property of 5,7-Dihydroxy-4-methylcoumarin

Chemical Property:

• Appearance/Colour: Yellow powder
• Vapor Pressure: 1.55E-09mmHg at 25°C
• Melting Point: 296-299 °C(lit.)
• Refractive Index: 1.651
• Boiling Point: 472.068 °C at 760 mmHg
• PKA: 7.29±0.20(Predicted)
• Flash Point: 197.851 °C
• PSA: 70.67000
• Density: 1.456 g/cm³
• LogP: 1.51260
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Sensitive.: Light Sensitive
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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:

99% ^*data from raw suppliers

5,7-Dihydroxy-4-methylcoumarin >98.0%(T) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC1=CC(=O)OC2=CC(=CC(=C12)O)O
• Uses: 5,7-Dihydroxy-4-methylcoumarin may be used in the synthesis of pyrano[2,3-h]coumarin derivatives and 5,7-dihydroxy-8-formyl-4-methylcoumarin.

Technology Process of 5,7-Dihydroxy-4-methylcoumarin

There total 19 articles about 5,7-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%

3,5-dihydroxyphenol (108-73-6) + acetoacetic acid methyl ester (105-45-3) → 4-methyl-5,7-dihydroxycoumarin (2107-76-8)

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%

3,5-dihydroxyphenol (108-73-6) + ethyl acetoacetate (141-97-9) → 4-methyl-5,7-dihydroxycoumarin (2107-76-8)

Guidance literature:

With scandium trifluoromethanesulphonate; at 80 ℃; for 1h;

DOI:10.1080/00397910802369513

Reference yield: 98.0%

3,5-dihydroxyphenol (108-73-6) + Methyl acetoacetate (4525-25-1) → 4-methyl-5,7-dihydroxycoumarin (2107-76-8)

Guidance literature:

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

upstream raw materials:

4-methyleneoxetan-2-one

3,5-dihydroxyphenol

ethyl acetoacetate

acetyl chloride

Downstream raw materials:

8-amino-5-hydroxy-4-methyl-2-oxo-10-(thiophen-2-yl)-2H,10Hpyrano[2,3-h]chromene-9-carbonitrile

8-amino-10-(3-bromophenyl)-5-hydroxy-4-methyl-2-oxo-2H,10H-pyrano[2,3-h]chromene-9-carbonitrile

8-amino-5-hydroxy-4-methyl-10-(4-methylphenyl)-2-oxo-2H,10H-pyrano[2,3-h]chromene-9-carbonitrile

8-amino-10-(4-chlorophenyl)-5-hydroxy-4-methyl-2-oxo-2,10-dihydropyrano[2,3-f]chromene-9-carbonitrile

Refernces

• 1、 Baghbanian, Seyed Meysam,Farhang, Maryam. "CuFe2O4 nanoparticles: A magnetically recoverable and reusable catalyst for the synthesis of coumarins via pechmann reaction in water". . p. 697 - 706. Retrieved 2014.
• 2、 Moradi, Leila,Rabiei, Khadijeh,Belali, Fateme. "Meglumine sulfate catalyzed solvent-free one-pot synthesis of coumarins under microwave and thermal conditions". . p. 1283 - 1291. Retrieved 2016.
• 3、 Sun, Rui,Gao, Yanjuan,Ma, Ying,Yang, Guangde,Li, Yiping. "SnCl4 grafted on silica gel: an efficient catalyst for solvent-free synthesis of coumarins via the Pechmann condensation". . p. 737 - 742. Retrieved 2017.
• 4、 Kumar, B. Sunil,Reddy, Y. Thirupathi,Reddy, P. Narsimha,Kumar,Rajitha. "Selectfluor: A simple and efficient catalyst for the synthesis of substituted coumarins under solvent-free conditions". . p. 477 - 479. Retrieved 2006.
• 5、 He, Haozhe,Ren, Yanrong,Dou, Yuge,Ding, Tao,Fang, Xiaomin,Xu, Yuanqing,Xu, Hao,Zhang, Wenkai,Xie, Zhigang. "Photo-cross-linked poly(ether amine) micelles for controlled drug release". . p. 105880 - 105888. Retrieved 2015.
• 6、 Karami, Bahador,Kiani, Mahtab. "Synthesis of the coumarins via pechmann method in the presence of environmentally friendly Y(NO3)3×6H2O". . p. 213 - 216. Retrieved 2014.
• 7、 Sabetpoor, Setareh,Hatamjafari, Farhad. "Synthesis of coumarin derivatives using glutamic acid under solvent-free conditions". . p. 863 - 865. Retrieved 2014.
• 8、 Kiani, Mahtab,Karami, Bahador. "Nanosilica molybdic acid: synthesis, characterization and application as a green and reusable catalyst for the Pechmann condensation". . p. 655 - 663. Retrieved 2017.
• 9、 Alexander, Varughese M.,Bhat, Ramakrishna P.,Samant, Shriniwas D.. "Bismuth(III) nitrate pentahydrate - A mild and inexpensive reagent for synthesis of coumarins under mild conditions". . p. 6957 - 6959. Retrieved 2005.
• 10、 Khandekar,Khadilkar. "Pechmann reaction in chloroaluminate ionic liquid". . p. 152 - 154. Retrieved 2002.