3-Methylcoumarin

Base Information

• Chemical Name: 3-Methylcoumarin
• CAS No.: 2445-82-1
• Molecular Formula: C10H8 O2
• Molecular Weight: 160.172
• Hs Code.: 2932209090
• European Community (EC) Number: 215-592-8,219-498-8
• NSC Number: 65664
• UNII: 9PCU0P29Z3
• DSSTox Substance ID: DTXSID201031385
• Nikkaji Number: J96.128K
• Wikidata: Q27272861
• Mol file: 2445-82-1.mol

Synonyms:3-Methylcoumarin;2445-82-1;3-METHYL-CHROMEN-2-ONE;Methyl-2-benzopyrone;COUMARIN, 3-METHYL-;3-Methyl-2H-chromen-2-one;3-methylchromen-2-one;2H-1-Benzopyran-2-one, 3-methyl-;3-Methyl-2H-1-benzopyran-2-one;1333-47-7;2H-1-Benzopyran-2-one, methyl-;EINECS 219-498-8;NSC 65664;BRN 0122776;UNII-5HV5045SSF;UNII-9PCU0P29Z3;9PCU0P29Z3;EINECS 215-592-8;NSC-65664;5-17-10-00165 (Beilstein Handbook Reference);methylcoumarin;3-Methylcumarin;Coumarin, methyl-;NSC65664;METHYLCOUMARIN, 3-;NCIOpen2_000275;SCHEMBL30023;5HV5045SSF;3-Methyl-2H-chromen-2-one #;DTXSID201031385;AKOS006271530;LS-55252;2H-1-Benzopyran-2-one, 3-methyl- (9CI);FT-0745305;F72673;10.14272/VIIIJFZJKFXOGG-UHFFFAOYSA-N.1;doi:10.14272/VIIIJFZJKFXOGG-UHFFFAOYSA-N.1;Q27272861

Chemical Property of 3-Methylcoumarin

Chemical Property:

• Melting Point: 91°C
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 292.5°Cat760mmHg
• Flash Point: 120.6°C
• PSA: 30.21000
• Density: 1.185g/cm³
• LogP: 2.10140
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 160.052429494
• Heavy Atom Count: 12
• Complexity: 230

Purity/Quality:

99% ^*data from raw suppliers

3-METHYL-CHROMEN-2-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=CC=CC=C2OC1=O

Technology Process of 3-Methylcoumarin

There total 64 articles about 3-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: 98.0%

salicylaldehyde (90-02-8) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → 3-methylcoumarine (2445-82-1) + ethyl (E)-3-(2-hydroxyphenyl)-2-methylacrylate (112021-87-1)

Guidance literature:

In benzene; for 2h; Ambient temperature;

DOI:10.1021/ja00209a040

Reference yield: 97.0%

salicylaldehyde (90-02-8) + propionic acid anhydride (123-62-6) → 3-methylcoumarine (2445-82-1)

Guidance literature:

With potassium carbonate; at 180 ℃; for 1.08333h; Microwave irradiation; Neat (no solvent);

DOI:10.1080/00397911.2010.487174

Reference yield: 94.0%

2H-chromene-3-carbaldehyde (51593-69-2) → 3-methylcoumarine (2445-82-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; In tetrahydrofuran; at 20 ℃; for 8h;

DOI:10.1039/c1ob05325f

upstream raw materials:

4-chloro-3-methyl-coumarin

3-(2-hydroxy-phenyl)-2-methyl-acrylic acid

salicylaldehyde

Ethyl 2-bromopropionate

Downstream raw materials:

4-(2-hydroxy-phenyl)-2,3-dimethyl-but-3-en-2-ol

3-(2-hydroxy-phenyl)-2-methyl-acrylic acid

Refernces

• 1、 Florekova, Lenka,Flasik, Radoslav,Stankovicova, Henrieta,Gaplovsky, Anton. "Efficient synthesis of 3-methyl-2H-chromen-2-one: Classic versus microwave conditions". . p. 1514 - 1519. Retrieved 2011.
• 2、 Sunitha, K.,Balasubramanian, K. K.,Rajagopalan, K.. "Thermal Rearrangement of α-(Aryloxy)methylacrylic Acids: A Facile Synthesis of 3-Methylcoumarins". . p. 1530 - 1531. Retrieved 1985.
• 3、 Dékány, Attila,Lázár, Enik?,Szabó, Bálint,Havasi, Viktor,Halasi, Gyula,Sápi, András,Kukovecz, ákos,Kónya, Zoltán,Sz?ri, Kornél,London, Gábor. "Exploring Pd/Al2O3 Catalysed Redox Isomerisation of Allyl Alcohol as a Platform to Create Structural Diversity". . p. 1834 - 1843. Retrieved 2017.
• 4、 Hu, Liang,Zhu, Rong-Mei,Qin, Jie,Zhou, Xin-Hui. "Synthesis and properties of a new coumarin functionalized tetrathiafulvalene derivative". . p. 573 - 578. Retrieved 2013.
• 5、 Li, Hanjie,Lin, Zhenwei,Lu, Ping,Qiao, Li,Wang, Yanguang,Xie, Jianwei,Zhang, Ke. "Visible-Light-Induced C(sp2)-C(sp3) Coupling Reaction for the Regioselective Synthesis of 3-Functionalized Coumarins". supporting information. p. 9552 - 9562. Retrieved 2021/07/26.
• 6、 ?erveny, Jakub,Bojarová, Pavla,Bumba, Ladislav,K?en, Vladimír,Pelantová, Helena,Petrásková, Lucie,Spiwok, Vojtěch,Va?í?ek, Tomá?,Vrbata, David. "Regioselective 3-O-Substitution of Unprotected Thiodigalactosides: Direct Route to Galectin Inhibitors". supporting information. p. 9620 - 9631. Retrieved 2020/08/05.