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(S)-(+)-3-Hydroxytetrahydrofuran

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(S)-(+)-3-Hydroxytetrahydrofuran Basic information

Product Name:
(S)-(+)-3-Hydroxytetrahydrofuran
Synonyms:
  • (S)-TETRAHYDROFURAN-3-OL
  • (S)-(+)-TETRAHYDRO-3-FURANOL
  • (S)-(+)-3-HYDROXY TETAHYDRO FURAN
  • (S)-(-)-3-HYDROXY TETRAHYDRO FURAN
  • (3S)-oxolan-3-ol
  • (2S)-1,4-Epoxy-2-hydroxybutane, (3S)-Tetrahydrofuran-3-ol, (3S)-Oxolan-3-ol
  • Afatinib intermediate B
  • (S)-(+)-3-Hydroxytetrahydrofuran, ee: 95%
CAS:
86087-23-2
MF:
C4H8O2
MW:
88.11
EINECS:
425-090-2
Product Categories:
  • Afatinib intermediate
  • Chiral Building Blocks
  • Chiral Reagents
  • Furans
  • Simple Alcohols (Chiral)
  • Synthetic Organic Chemistry
  • Alcohols, Hydroxy Esters and Derivatives
  • Chiral Compounds
  • Starting Raw Materials & Intermediates
  • Small molecule
  • Tetrahydrofuran Series
  • bc0001
  • 86087-23-2
  • john's
  • ADVANCED INT.
  • 1
Mol File:
86087-23-2.mol
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(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)
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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

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(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.

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.

(S)-(+)-3-Hydroxytetrahydrofuran Preparation Products And Raw materials

Raw materials

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