TETRAHYDROTHIOPYRAN-4-OL 97 Chemical Properties

Melting point:

47-51 °C (lit.)

Boiling point:

70°C/0.05mmHg(lit.)

Density 

1.148±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to lump

pka

14.56±0.20(Predicted)

color 

White to Almost white

Safety Information

RIDADR 

UN 3335

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2934999090

TETRAHYDROTHIOPYRAN-4-OL 97 Usage And Synthesis

General Description

Tetrahydrothiopyran-4-ol is a sulfur containing heterocyclic building block. Tetrahydrothiopyran-4-ol can be synthesized from tetrahydrothiopyran-4-one. It participates in the synthesis of 4-hydroxyl-1-methyltetrahydrothiopyranium iodide.

Synthesis

GENERAL METHOD: Tetrahydrothiopyran-4-one (40.10 g, 0.271 mol) was dissolved in methanol (700 mL), and sodium borohydride (15.36 g, 0.406 mol) was added in batches under ice-bath cooling, and the reaction was stirred for 1 hr. (NOTE: the reaction is exothermic and violent). Subsequently, the reaction mixture was continued to be stirred at 20°C for 2 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure to give a solid residue. To the residue was added a mixture of saturated aqueous sodium bicarbonate (150 mL) and ethyl acetate (250 mL) (Note: the product is soluble in water). After vigorous shaking, the organic layer was separated and the aqueous layer was further extracted with ethyl acetate (4 x 250 mL). All organic layers were combined, dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure to give the target product tetrahydro-2H-thiopyran-4-ol.

References

[1] Synthetic Communications, 2018, vol. 48, # 17, p. 2198 - 2205
[2] Chemistry - A European Journal, 2018, vol. 24, # 62, p. 16526 - 16531
[3] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 9, p. 2739 - 2750
[4] Chemical Communications (Cambridge, United Kingdom), 2002, # 10, p. 1070 - 1071
[5] Patent: EP3342765, 2018, A1. Location in patent: Paragraph 0337

TETRAHYDROTHIOPYRAN-4-OL 97(29683-23-6)Related Product Information

• Tetrahydrothiopyran-4-one
• Tetrahydrothiophen-3-one
• Oxan-4-yl 4-methylbenzenesulfonate
• Tetrahydro-2H-pyran-4-carbonyl chloride
• Tetrahydro-4-pyranol
• Hexahydro-3H-pyrrolo[1,2-c]imidazole-1,3-dione
• TETRAHYDRO-2H-PYRAN-3-CARBOXYLIC ACID
• 1,1-Dioxo-hexahydro-1l6-thiopyran-4-carboxylic acid
• tetrahydro-2H-thiopyran-4-ol 1,1-dioxide(SALTDATA: FREE)
• (TETRAHYDRO-THIOPYRAN-4-YL)-ACETALDEHYDE
• THIAZOLIDINE
• Tetrahydro-2H-thiopyran-4-amine
• 2H-Thiopyran-4-methanol, tetrahydro-
• 4-Amidinotetrahydro-2H-pyran hydrochloride
• TETRAHYDROFURAN-3-BORONIC ACID
• Methyl tetrahydro-3-furoate
• 2-Furamide,tetrahydro-(6CI,7CI)
• Tetrahydro-2-furancarboxaldehyde