Tetrahydrothiopyran-4-one

Base Information

• Chemical Name: Tetrahydrothiopyran-4-one
• CAS No.: 1072-72-6
• Molecular Formula: C5H8OS
• Molecular Weight: 116.184
• Hs Code.: 29349990
• European Community (EC) Number: 214-015-7
• NSC Number: 41599
• UNII: 667X5M356L
• DSSTox Substance ID: DTXSID40147948
• Nikkaji Number: J113.728J
• Wikidata: Q27263968
• Mol file: 1072-72-6.mol

Synonyms:4H-Thiopyran-4-one,tetrahydro-;1-Thiacyclohexan-4-one;2,3,5,6-Tetrahydro-4-thiopyranone;4-Oxotetrahydrothiopyran;4-Oxothiane;4-Thiacyclohexan-1-one;4-Thiacyclohexanone;4-Thianone;NSC 41599;Penthianone;Tetrahydro-1-thio-4-pyrone;Tetrahydro-1-thio-g-pyrone;Tetrahydro-4-thiopyrone;Tetrahydrothiapyran-4-one;Tetrahydro-4H-thiopyran-4-one;

Chemical Property of Tetrahydrothiopyran-4-one

Chemical Property:

• Appearance/Colour: White to pale yellow crystalline solid
• Vapor Pressure: 0.124mmHg at 25°C
• Melting Point: 60-64 °C(lit.)
• Refractive Index: 1.524
• Boiling Point: 218.7 °C at 760 mmHg
• Flash Point: 105.5 °C
• PSA: 42.37000
• Density: 1.134 g/cm³
• LogP: 1.08250
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 116.02958605
• Heavy Atom Count: 7
• Complexity: 72.1

Purity/Quality:

99% ^*data from raw suppliers

Tetrahydro-2H-thiopyran-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CSCCC1=O
• Uses: Tetrahydro-?4H-?thiopyran-?4-?one is a cyclic carbonyl compound used as a reactant in the stereoselective preparation of [aryl(nitro)ethyl] carbonyl compounds via asymmetric Michael addition to nitroolefins catalyzed by chiral pyrrolidine-pyridine conjugate bases.

Technology Process of Tetrahydrothiopyran-4-one

There total 19 articles about Tetrahydrothiopyran-4-one 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: 91.0%

tetrahydro-4H-thiopyran-4-one 1-oxide (17396-36-0) → Tetrahydrothiopyran-4-one (1072-72-6)

Guidance literature:

With hydrogen; In 1,4-dioxane; at 100 ℃; for 8h; under 760.051 Torr; chemoselective reaction;

DOI:10.1002/anie.201403425

Reference yield: 91.0%

3-methoxycarbonyltetrahydropyran-4-one (4160-61-6) → Tetrahydrothiopyran-4-one (1072-72-6)

Guidance literature:

With sulfuric acid; for 5h; Heating;

DOI:10.1021/jo00385a011

Reference yield: 76.0%

tetrahydrothiopyran-4-one-3-carboxylic acid allyl ester (126573-38-4) → Tetrahydrothiopyran-4-one (1072-72-6)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; Ambient temperature;

DOI:10.1055/s-1989-27389

upstream raw materials:

3-methoxycarbonyltetrahydropyran-4-one

diethyl 3,3'-thiobispropionate

1-bromo-5-chloro-3-pentanone

tetrahydrothiopyran-4-ol

Downstream raw materials:

thiepan-4-one

1-oxa-6-thiaspiro<2.5>octane

3-phenyl-8-thia-1,4-diaza-spiro[4.5]dec-3-ene-2-thione

5-benzyl-1,3,4,5-tetrahydro-thiopyrano[4,3-b]indole-8-carboxylic acid ethyl ester

Refernces

• 1、 Ward, Dale E.,Rasheed, M. Abdul,Gillis, H. Martin,Beye, Garrison E.,Jheengut, Vishal,Achonduh, George T.. "Simple and efficient preparation of reagents for thiopyran introduction: Methyl tetrahydro-4-oxo-2H-thiopyran-3-carboxylate, tetrahydro-4H-thiopyran-4- one, and 3,6-dihydro-4-trimethylsilyloxy-2H-thiopyran". . p. 1584 - 1586. Retrieved 2007.
• 2、 Fehnel,Carmack. "-". . p. 1813,1816. Retrieved 1948.
• 3、 Mitsudome, Takato,Takahashi, Yusuke,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi. "Hydrogenation of sulfoxides to sulfides under mild conditions using ruthenium nanoparticle catalysts". supporting information. p. 8348 - 8351. Retrieved 2014/08/18.