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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

• Language:English Provider:4-Thiacyclohexanone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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 (1072-72-6)Related Product Information

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