3,4-Dihydrocoumarin

Base Information

• Chemical Name: 3,4-Dihydrocoumarin
• CAS No.: 119-84-6
• Deprecated CAS: 1341-36-2
• Molecular Formula: C9H8O2
• Molecular Weight: 148.161
• Hs Code.: 29322980
• European Community (EC) Number: 204-354-9
• NSC Number: 10121
• UNII: NM5K1Y1BT2
• DSSTox Substance ID: DTXSID2020474
• Nikkaji Number: J36.832F
• Wikidata: Q27098403
• Metabolomics Workbench ID: 47423
• ChEMBL ID: CHEMBL89306
• Mol file: 119-84-6.mol

Synonyms:3,4-dihydrocoumarin

Chemical Property of 3,4-Dihydrocoumarin

Chemical Property:

• Appearance/Colour: Colorless to pale yellow clear liquid
• Vapor Pressure: 0.00624mmHg at 25°C
• Melting Point: 24-25 °C(lit.)
• Refractive Index: n20/D 1.556(lit.)
• Boiling Point: 272 °C at 760 mmHg
• Flash Point: 108.4 °C
• PSA: 26.30000
• Density: 1.169 g/cm³
• LogP: 1.53820
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform, Methanol (Sparingly)
• Water Solubility.: insoluble
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 148.052429494
• Heavy Atom Count: 11
• Complexity: 165

Purity/Quality:

99% ^*data from raw suppliers

Hydrocoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1CC(=O)OC2=CC=CC=C21
• Description: With a sweet, creamy, and herbal, fragrance, with a slightly burnt taste, dihydrocoumarin (DHC) is used as a flavoring agent in food, tobacco, soap, and perfume, etc. Its exotic flavor is well suited for caramel, nuts, dairy, vanilla, tropical fruit, and alcohol. It is a eukaryotic metabolite found in tonka beans grown in northern South America, from which it was isolated as early as the 1820s, as well as sweet clover. Other uses include as an organic solvent and pharmaceutical intermediary. It has been shown to influence the epigenetic process of human cells in vitro.
• Uses: Hydrocoumarin can be used as a reagent to prepare splitomicin analogs as inhibitors of Sir2. Dihydrocoumarin may be used as an analytical reference standard for the determination of the analyte in guaco extracts and pharmaceutical preparations, and various plant extracts by chromatography-based techniques and capillary electrophoresis.

Technology Process of 3,4-Dihydrocoumarin

There total 85 articles about 3,4-Dihydrocoumarin 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%

palladium-on-activated carbon + Pd-on-carbon Powder + methyl 3-(2-oxocyclohexyl)propionate (10407-33-7,58769-44-1) → coumarin (91-64-5) + C6H4(CH2CH2C(O)O) (119-84-6,1341-36-2)

Guidance literature:

In methyl 3-(2-oxcyclohexyl)propionate;

Reference yield: 100.0%

coumarin (91-64-5) → C6H4(CH2CH2C(O)O) (119-84-6,1341-36-2)

Guidance literature:

With formic acid; palladium; In methanol; water; Ambient temperature;

DOI:10.1016/S0040-4039(00)80822-9

Reference yield: 99.9%

→ coumarin (91-64-5) + C6H4(CH2CH2C(O)O) (119-84-6,1341-36-2)

Guidance literature:

upstream raw materials:

benzofurane-3-carboxylic acid

3,3-Dimethylacryloyl chloride

5-methoxyresorcinol

2-oxochroman-3-carboxylic acid

Downstream raw materials:

3-[5-(2,3-Dichloro-5,6-dicyano-4-hydroxy-phenoxy)-2-hydroxy-phenyl]-propionic acid methyl ester

3-[5-(2,3-Dichloro-5,6-dicyano-4-hydroxy-phenoxy)-2-hydroxy-phenyl]-propionic acid ethyl ester

3-(2-hydroxyphenyl)-propionamide

coumarin

Refernces

• 1、 Odaira,Tsutsumi. "-". . p. 564. Retrieved 1959.
• 2、 Alam, M. Mujahid,Varala, Ravi,Adapa, Srinivas R.. "Bi(OTf)3-catalyzed Baeyer-Villiger oxidation of carbonyl compounds with m-CPBA". . p. 3035 - 3040. Retrieved 2003.
• 3、 Pickett, James E.,Van Dort, Paul C.. "An efficient synthesis of dihydrocoumarins". . p. 1161 - 1164. Retrieved 1992.
• 4、 Karakhanov, E. A.,Dedov, A. G.,Loktev, A. S.. "HYDROGENATION OF OXYGEN-CONTAINING HETEROCYCLIC COMPOUNDS ON GROUP VIII METALS". . p. 993 - 995. Retrieved 1981.
• 5、 Johnston,Gross. "-". . p. 1264. Retrieved 1957.
• 6、 Schwartz, Thomas J.,Lyman, Spencer D.,Motagamwala, Ali Hussain,Mellmer, Max A.,Dumesic, James A.. "Selective Hydrogenation of Unsaturated Carbon-Carbon Bonds in Aromatic-Containing Platform Molecules". . p. 2047 - 2054. Retrieved 2016.
• 7、 Ye, Fangguo,Alper, Howard. "Recyclable selective palladium-catalyzed synthesis of five-, six- or seven-membered ring lactones and lactams by cyclocarbonylation in ionic liquids". . p. 1855 - 1861. Retrieved 2006.
• 8、 Larionova, Natalia A.,Ondozabal, Jun Miyatake,Cambeiro, Xacobe C.. "Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer". supporting information. p. 558 - 564. Retrieved 2020/12/07.
• 9、 Li, Tingting,Hammond, Gerald B.,Xu, Bo. "Cobalt-Catalyzed Aerobic Oxidative Cleavage of Alkyl Aldehydes: Synthesis of Ketones, Esters, Amides, and α-Ketoamides". supporting information. p. 9737 - 9741. Retrieved 2021/05/31.