(S)-(+)-3-Hydroxytetrahydrofuran Chemical Properties

Boiling point:

80 °C/15 mmHg (lit.)

alpha 

18.5 º (c=2 MeOH)

Density 

1.103 g/mL at 25 °C (lit.)

vapor pressure 

47Pa at 25℃

refractive index 

n20/D 1.45(lit.)

Flash point:

175 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol (Slightly)

pka

14.49±0.20(Predicted)

form 

Liquid

Specific Gravity

1.11

color 

Clear colorless to pale yellow

optical activity

[α]20/D +17.5°, c = 2.4 in methanol

Water Solubility 

soluble

BRN 

4652609

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

XDPCNPCKDGQBAN-BYPYZUCNSA-N

LogP

-0.784 at 22℃ and pH6.8

Surface tension

72mN/m at 1g/L and 25℃

CAS DataBase Reference

86087-23-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

HS Code 

29321900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(S)-(+)-3-Hydroxytetrahydrofuran Usage And Synthesis

Description

(S)-(+)-3-Hydroxytetrahydrofuran (3-OH THF) is a colorless liquid with a normal boiling point of 179 °C and boiling at 88-89 °C at 17 mmHg, with density (1.087 g/cm3 at 19 °C). 3-OH THF is a useful pharmaceutical intermediate. The chiral (absolute configuration S) version of this compound is an intermediate to launched retroviral drugs.

Chemical Properties

Colourless Liquid

Uses

(S)-(+)-3-Hydroxytetrahydrofuran is a useful reagent for the preparation of pyrazolo triazin ylamine derivatives as adenosine receptor antagonists.

Uses

(S)-(+)-3-Hydroxytetrahydrofuran is an intermediate to the AIDS drugs amprenavir and fosamprenavir. Additionally, it has been an intermediate to developmental drug substances, such as chemotherapy agents.

Application

(S)-(+)-3-Hydroxytetrahydrofuran is used as a synthetic intermediate for Empagliflozin, Afatinib and GS-9669.

Synthesis

(S)-(+)-3-Hydroxytetrahydrofuran was prepared from the reaction of (S)-1,2,4-butanetriol under hydrochloric acid modified montmorillonite catalyst. The steps were as follows：To the heatable reactor (with stirring device), 100g (S)-1,2,4-butanetriol, 200mL toluene, 15g hydrochloric acid modified montmorillonite catalyst prepared in were added successively. The reaction was stopped after 4 h at 110°C. After the reaction is finished, it is naturally cooled to room temperature, and the obtained material is filtered to recover the catalyst. After collecting the filtrate, the remaining solvent and by-product water in the filtrate are distilled off to obtain (S)-3-hydroxytetrahydrofuran crude product. Quantitative analysis was carried out by gas chromatography, and the yield was 96.8%. Finally, the (S)-3-hydroxytetrahydrofuran was obtained by rectification and purification.

References

[1] Journal of Organic Chemistry, 1983, vol. 48, # 16, p. 2767 - 2769
[2] Patent: WO2007/81065, 2007, A1. Location in patent: Page/Page column 5
[3] Patent: WO2007/81065, 2007, A1. Location in patent: Page/Page column 6; 7
[4] Patent: US5576343, 1996, A

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