3,4-Dihydro-6-methylcoumarin

Base Information

• Chemical Name: 3,4-Dihydro-6-methylcoumarin
• CAS No.: 92-47-7
• Molecular Formula: C10H10 O2
• Molecular Weight: 162.188
• Hs Code.: 2932209090
• European Community (EC) Number: 202-157-2
• NSC Number: 19513
• UNII: 8FQ6538M2N
• DSSTox Substance ID: DTXSID8059055
• Nikkaji Number: J182.087G
• Wikidata: Q27270340
• Mol file: 92-47-7.mol

Synonyms:92-47-7;3,4-Dihydro-6-methylcoumarin;6-Methyl-3,4-dihydrocoumarin;6-Methylhydrocoumarin;6-Methylchroman-2-one;6-methyl-3,4-dihydrochromen-2-one;Hydrocoumarin, 6-methyl-;3,4-Dihydro-6-methyl-2H-1-benzopyran-2-one;6-METHYLCHROMANONE;2H-1-Benzopyran-2-one, 3,4-dihydro-6-methyl-;6-Methyl-2-chromanone;UNII-8FQ6538M2N;8FQ6538M2N;EINECS 202-157-2;NSC 19513;NSC-19513;AI3-24744;NSC19513;6-methyl-chroman-2-one;6-Methyl-2-chromanone #;6-Methylchromanone, AldrichCPR;SCHEMBL3504905;DTXSID8059055;2H-1-Benzopyran-2-one,4-dihydro-6-methyl-;6-Methyl-3,4-dihydro-2H-1-benzopyran-2-one;Q27270340

Chemical Property of 3,4-Dihydro-6-methylcoumarin

Chemical Property:

• Vapor Pressure: 0.00234mmHg at 25°C
• Boiling Point: 288.4°C at 760 mmHg
• Flash Point: 116.5°C
• PSA: 26.30000
• Density: 1.157g/cm³
• LogP: 1.84660
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 162.068079557
• Heavy Atom Count: 12
• Complexity: 188

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)OC(=O)CC2

Technology Process of 3,4-Dihydro-6-methylcoumarin

There total 12 articles about 3,4-Dihydro-6-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: 100.0%

6-methylcoumarin (92-48-8) → 3,4-dihydro-6-methyl-2H-1-benzopyran-2-one (92-47-7)

Guidance literature:

With hydrogen; 20 % Pd(OH)2/C; In tetrahydrofuran; at 50 ℃; for 2h; under 4654.46 Torr;

Reference yield: 80.0%

(±)-6-methylchroman-2-ol (85960-67-4) → 3,4-dihydro-6-methyl-2H-1-benzopyran-2-one (92-47-7)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In benzene; for 10h; Heating;

DOI:10.1016/j.tetlet.2003.10.174

Reference yield: 54.0%

2-hydroxy-5-methylcinnamaldehyde (1119700-53-6) → 3,4-dihydro-6-methyl-2H-1-benzopyran-2-one (92-47-7) + 6-methylcoumarin (92-48-8)

Guidance literature:

With dmap; 4-mesityl-3-(4-methoxyphenyl)-1-phenyl-4H-1,2,4-triazol-1-ium perchlorate; In ethyl acetate; at 80 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jo802285r

upstream raw materials:

3-Chloropropionitrile

p-cresol

6-methylcoumarin

methyl-6 diethoxy-2,2 benzopyranne-1

Downstream raw materials:

C₁₁H₁₇NO₃S

N-(3-(2-hydroxyphenyl)propyl)ethenesulfonamide

C₁₂H₁₇NO₃S

N-(3-(2-(tert-butyldimethylsilyloxy)phenyl)propyl)ethene sulfonamide

Refernces

• 1、 Jiang, Ze-Zhen,Gao, Ang,Li, Hao,Chen, Di,Ding, Chang-Hua,Xu, Bin,Hou, Xue-Long. "Enantioselective Synthesis of Chromenes via a Palladium-Catalyzed Asymmetric Redox-Relay Heck Reaction". supporting information. p. 3119 - 3122. Retrieved 2017/12/04.
• 2、 Farndon, Joshua J.,Ma, Xiaofeng,Bower, John F.. "Transition Metal Free C-N Bond Forming Dearomatizations and Aryl C-H Aminations by in Situ Release of a Hydroxylamine-Based Aminating Agent". supporting information. p. 14005 - 14008. Retrieved 2017/10/17.