6-Methyl-4-phenylcoumarin

Base Information

• Chemical Name: 6-Methyl-4-phenylcoumarin
• CAS No.: 16299-22-2
• Molecular Formula: C16H12O2
• Molecular Weight: 236.27
• Mol file: 16299-22-2.mol

Synonyms:6-Methyl-4-phenyl-cumarin;6-methyl-4-phenylcoumarin;6-Methyl-4-phenyl-2H-1-benzopyran-2-one;6-Methyl-4-phenyl-2H-chromen-2-one;6-methyl-4-phenyl-chromen-2-one;4-phenyl-6-methylcoumarin;

Chemical Property of 6-Methyl-4-phenylcoumarin

Chemical Property:

• Melting Point: 132-134°C
• PSA: 30.21000
• LogP: 3.76840
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

6-Methyl-4-phenylcoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the production ot Tolterodine and related coumarin derivatives.

Technology Process of 6-Methyl-4-phenylcoumarin

There total 52 articles about 6-Methyl-4-phenylcoumarin 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: 97.0%

triphenylindium (3958-47-2) + 6-methyl-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate (345948-96-1) → 6-methyl-4-phenylchromen-2-one (16299-22-2)

Guidance literature:

With palladium diacetate; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.10.096

Reference yield: 97.0%

4-bromo-6-methyl-2H-chromen-2-one (1239896-43-5) + triphenylbismuthane (603-33-8) → 6-methyl-4-phenylchromen-2-one (16299-22-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In N,N-dimethyl acetamide; at 90 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.201000134

Reference yield: 92.0%

4-methylphenyl 3-phenylpropiolate (20984-26-3) → 6-methyl-4-phenylchromen-2-one (16299-22-2)

Guidance literature:

With Pd nanocrystals on a preinstalled iron oxide core inside a hollow silica nanoshell; In water; acetonitrile;

DOI:10.1021/acs.nanolett.0c01507

upstream raw materials:

6-methyl-4-phenyl-3,4-dihydrocoumarin

4-methylphenyl 3-phenylpropiolate

p-cresol

ethyl 3-oxo-3-phenylpropionate

Downstream raw materials:

(R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one

(S)-6-methyl-4-phenylchroman-2-one

(4R)-6-methyl-4-phenylchroman-2-ol

3-phenyl-3-(2'-hydroxy-5'-methyl)phenylpropanol-1

Refernces

• 1、 Zaitceva, Olesia,Bénéteau, Valérie,Ryabukhin, Dmitry S.,Eliseev, Ivan I.,Kinzhalov, Mikhal A.,Louis, Benoit,Vasilyev, Aleksander V.,Pale, Patrick. "Cyclization of aryl 3-aryl propynoates into 4-arylcoumarins catalyzed by cyclometalated Platinum(II) complexes". supporting information. . Retrieved 2020/03/05.
• 2、 Fernandes, Rodney A.,Gangani, Ashvin J.,Kunkalkar, Rupesh A.. "Metal-free annulative hydrosulfonation of propiolate esters: synthesis of 4-sulfonates of coumarins and butenolides". . p. 3970 - 3984. Retrieved 2020/03/19.