Tetrahydro-4-pyranol Chemical Properties

Boiling point:

87 °C/15 mmHg (lit.)

Density 

1.071 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.462(lit.)

Flash point:

190 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Oil

pka

14.61±0.20(Predicted)

color 

Clear Colourless

BRN 

102736

InChI

InChI=1S/C5H10O2/c6-5-1-3-7-4-2-5/h5-6H,1-4H2

InChIKey

LMYJGUNNJIDROI-UHFFFAOYSA-N

SMILES

C1OCCC(O)C1

LogP

-0.440 (est)

CAS DataBase Reference

2081-44-9(CAS DataBase Reference)

NIST Chemistry Reference

Tetrahydro-4H-pyran-4-ol(2081-44-9)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

41-36/37/38-20/22

Safety Statements 

26-39-36/37/39-23

RIDADR 

1993

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29329990

MSDS

• Language:English Provider:Tetrahydro-4-pyranol
• Language:English Provider:SigmaAldrich

Tetrahydro-4-pyranol Usage And Synthesis

Chemical Properties

Colorless transparent liquid

Uses

Tetrahydro-4-pyranol (4-Hydroxytetrahydropyran) was used in the quantitative analysis of 3-hydroxytetrahydropyran (3-HTHP).

Uses

Tetrahydro-4-pyranol is a building block of various organic compounds and pharmaceuticals.

Synthesis

General procedure for the synthesis of tetrahydropyran-4-ol from tetrahydropyranone: To a tetrahydrofuran (THF, 25 mL) solution of tetrahydropyranone (5.0 g, 50 mmol), which was cooled to 0 °C, a THF (50 mL) suspension of lithium aluminum hydride (LiAlH4, 3.8 g, 0.1 mol) was slowly added. The reaction mixture was stirred at 0 °C for 30 min, followed by sequential addition of water (3.8 mL), 15% aqueous sodium hydroxide (NaOH) solution (3.8 mL) and water (11.4 mL) to quench the reaction. The mixture was filtered and the solid was washed with ethyl acetate (70 mL x 2). The filtrates were combined and evaporated to give tetrahydropyran-4-ol (5.09 g, 99% yield).

References

[1] Patent: WO2008/88881, 2008, A1. Location in patent: Page/Page column 39
[2] Patent: US9301951, 2016, B2. Location in patent: Page/Page column 125
[3] Chemistry - A European Journal, 2018, vol. 24, # 62, p. 16526 - 16531
[4] Patent: US2010/76029, 2010, A1. Location in patent: Page/Page column 35
[5] Patent: US2011/71196, 2011, A1. Location in patent: Page/Page column 18-19

Tetrahydro-4-pyranol(2081-44-9)Related Product Information

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• TETRAHYDROTHIOPYRAN-4-OL 97
• TETRAHYDRO-2H-PYRAN-3-CARBOXYLIC ACID
• 1,1-Dioxo-hexahydro-1l6-thiopyran-4-carboxylic acid
• Tetrahydropyranyl-4-acetic acid