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| | Tetrahydrothiopyran-4-one Basic information |
| | Tetrahydrothiopyran-4-one Chemical Properties |
| Melting point | 60-64 °C (lit.) | | Boiling point | 140.82°C (estimate) | | density | 1.050 (estimate) | | refractive index | 1.5100 (estimate) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Acetonitrile (Slightly), Chloroform (Slightly) | | form | Crystalline Solid | | color | White to pale yellow | | BRN | 106464 | | InChIKey | OVRJVKCZJCNSOW-UHFFFAOYSA-N | | LogP | 0.490 (est) | | CAS DataBase Reference | 1072-72-6(CAS DataBase Reference) | | NIST Chemistry Reference | 4H-Thiopyran-4-one, tetrahydro-(1072-72-6) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 22-24/25 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29349990 |
| | Tetrahydrothiopyran-4-one Usage And Synthesis |
| Chemical Properties | WHITE TO PALE YELLOW CRYSTALLINE SOLID | | 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. | | General Description | The diastereoselectivity of the aldol reaction of tetrahydro-4H-thiopyran-4-one has been studied. | | Purification Methods | Purify it by recrystallisation from diisopropyl ether or pet ether and dry it in air. If too impure, then dissolve it in Et2O, wash with aqueous NaHCO3, then H2O, dry (MgSO4), filter, evaporate and the residue is recrystallised as before. [Cardwell J Chem Soc 715 1949.] The oxime can be recrystallised from CHCl3/pet ether (at -20o) and has m 84-85o [Barkenbus et al. J Org Chem 20 871 1955]. The 2,4-dinitrophenylhydrazone has m 186o (from EtOAc) [Barkenbus et al. J Org Chem 16 232 1951]. The S-dioxide is recrystallised from AcOH, m 173-174o [Fehnel & Carmack J Am Chem Soc 70 1813 1948, Beilstein 17 II 287, 17 III/IV 4172, 17/1 V 21]. |
| | Tetrahydrothiopyran-4-one Preparation Products And Raw materials |
| Raw materials | Propanoic acid, 3,3'-thiobis-, di-2-propenyl ester (9CI)-->4H-Thiopyran-4-one, 2,3-dihydro--->2H-Thiopyran, 3,6-dihydro-4-[(trimethylsilyl)oxy]--->1,4-dioxa-8-thiaspiro<4.5>decane-6-carboxaldehyde
-->Thian-4-one S-oxide-->METHYL TETRAHYDRO-4-OXO-2H-THIOPYRAN-3-CARBOXYLATE-->TETRAHYDROTHIOPYRAN-4-OL 97-->Dimethyl 3,3'-thiodipropanoate-->1,5-DIBROMO-PENTAN-3-ONE-->diethyl 3,3'-thiobispropionate-->PIPERIDINIUM, 1,1-DIMETHYL-4-OXO-, IODIDE-->3,3'-Thiodipropionic acid | | Preparation Products | Tetrahydrothiopyran-4-one oxiMe-->4-Aminotetrahydrothiopyran-4-carbonitrile-->Thiopyrano[4,3-c]pyrazole, 1,4,6,7-tetrahydro--->N-methyltetrahydro-2H-thiopyran-4-amine(SALTDATA: HCl) |
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