4-Methylcoumarin

Base Information

• Chemical Name: 4-Methylcoumarin
• CAS No.: 607-71-6
• Molecular Formula: C10H8O2
• Molecular Weight: 160.172
• Hs Code.: 2932209090
• European Community (EC) Number: 210-141-1
• NSC Number: 20100
• UNII: 2YZ8R79U9H
• DSSTox Substance ID: DTXSID00209516
• Nikkaji Number: J48.498I
• Wikidata: Q27097965
• Metabolomics Workbench ID: 151900
• ChEMBL ID: CHEMBL12279
• Mol file: 607-71-6.mol

Synonyms:4-Methylcoumarin;607-71-6;4-Methyl-2H-chromen-2-one;4-methylchromen-2-one;4-Methylcumarin;COUMARIN, 4-METHYL-;4-Methyl-chromen-2-one;2H-1-Benzopyran-2-one, 4-methyl-;4-Methyl-2H-1-benzopyran-2-one;EINECS 210-141-1;NSC 20100;BRN 0121648;UNII-2YZ8R79U9H;2YZ8R79U9H;NSC20100;NSC-20100;2H-1-Benzopyran-2-one, 4-methyl- (9CI);4-METHYLUMBELLIFERYL;METHYLCOUMARIN, 4-;SCHEMBL66891;CHEMBL12279;4-methyl-1-benzopyran-2-one;WLN: T66 BOVJ E1;4-Methyl-2H-chromen-2-one #;DTXSID00209516;HMS1693J19;BCP28723;MFCD00185474;AKOS000277307;DB08785;AS-17408;LS-55253;FT-0602250;M3041;A832878;Q27097965

Chemical Property of 4-Methylcoumarin

Chemical Property:

• Appearance/Colour: White needle crystal
• Vapor Pressure: 0.0014mmHg at 25°C
• Melting Point: 79.0 to 83.0 °C
• Refractive Index: 1.572
• Boiling Point: 296.895 °C at 760 mmHg
• Flash Point: 120.635 °C
• PSA: 30.21000
• Density: 1.185 g/cm³
• LogP: 2.10140
• Storage Temp.: 2-8°C
• 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:

97% ^*data from raw suppliers

4-Methylcoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=CC=CC=C12

Technology Process of 4-Methylcoumarin

There total 126 articles about 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: 98.0%

ethyl acetoacetate (141-97-9) + phenol (108-95-2,27073-41-2) → 4-methyl-2H-chromen-2-one (607-71-6)

Guidance literature:

With tetrakis(actonitrile)copper(I) hexafluorophosphate; at 25 ℃; for 0.5h; neat (no solvent);

DOI:10.1002/jhet.814

Reference yield: 96.0%

acetoacetic acid methyl ester (105-45-3) + phenol (108-95-2,27073-41-2) → 4-methyl-2H-chromen-2-one (607-71-6)

Guidance literature:

With Fe₃O₄-SiO₂-HMTA nanomaterial; In neat (no solvent); at 100 ℃; for 0.2h; Green chemistry;

DOI:10.1007/s13738-015-0652-6

Reference yield: 96.0%

o-iodophenyl 3-butenoate → 4-methyl-2H-chromen-2-one (607-71-6)

Guidance literature:

With silver(I) acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In various solvent(s); at 80 ℃; for 24h;

DOI:10.1016/S0022-328X(96)06489-3

upstream raw materials:

phenyl acetoacetate

4-methyl-2-oxo-2H-chromene-3-carbonitrile

(2-oxo-2H-chromen-4-yl)-acetic acid

o-acetoxyacetophenone

Downstream raw materials:

2,2,4-trimethyl-2H-benzopyran

4-(2-hydroxy-phenyl)-2-methyl-pent-3-en-2-ol

4-methyl-2H-1-benzopyran-2-thione

6-hydroxy-4-methyl-chromen-2-one

Refernces

Designing a catalytic synthesis of 4-methylcoumarin from ortho-iodophenyl 3-butenoate: Ring closure and isomerization control

10.1016/S0022-328X(96)06489-3

The research investigates the catalytic synthesis of 4-methylcoumarin from ortho-iodophenyl 3-butenoate using palladium complexes. The purpose is to control the ring closure and isomerization processes to achieve high yields of the desired cyclic compound. Key chemicals involved include palladium(0) complexes, such as Pd(dba)2 and Pd(PPh3)4, along with ligands like triphenylphosphine and bis(diphenylphosphino)ferrocene (dppf), solvents like anisole and dimethylformamide (DMF), and neutralizing agents like potassium butyrate and magnesium oxide. The study concludes that by carefully selecting ligands, solvents, and neutralizing agents, and by controlling reaction conditions, it is possible to achieve quantitative yields of 4-methylcoumarin. Specifically, the use of dppf in conjunction with Pd(PPh3)4 in DMF with MgO under nitrogen resulted in a 100% yield of the desired product, demonstrating effective control over the competing reactions.