3-hydroxytetrahydrofuran

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	3-hydroxytetrahydrofuran
other names	Oxolan-3-ol ( IUPAC ) ; 3-hydroxyoxolane;
Molecular formula	C 4 H 8 O 2
Brief description	colorless liquid
External identifiers / databases
EC number	207-219-2
ECHA InfoCard	100.006.564
PubChem	9960
ChemSpider	9566
Wikidata	Q4634149
properties
Molar mass	88.11 g mol −1
Physical state	liquid
density	1.09 g cm −3 (25 ° C)
boiling point	181 ° C
Refractive index	1.45 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319
	P: 210-264-280-302-352-332-313-362-364-305-351-338-337-313-403 + 235-501
Toxicological data	3850 mg kg −1 ( LD 50 , mouse , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

3-Hydroxytetrahydrofuran is a chemical compound belonging to the furans group .

synthesis

3-Hydroxytetrahydrofuran was produced by M. Pariselle in 1910 by the cyclization and hydrolysis of 3,4-dibromo-1-methoxybutane .

Stereochemistry

3-Hydroxytetrahydrofuran is chiral . Enantiomerically pure 3-hydroxytetrahydrofuran can be synthesized with high purity from ( S ) - or ( R ) - 1,2,4-butanetriol . Thus, the ( S ) -1,2,4-butanetriol can be cyclized to ( S ) -3-hydroxytetrahydrofuran in the presence of catalytic amounts of p -toluenesulfonic acid at temperatures from 180 to 220.degree .

properties

3-Hydroxytetrahydrofuran is a colorless liquid.

use

3-Hydroxytetrahydrofuran can be used as an intermediate in the manufacture of other chemical compounds (such as the drugs amprenavir and fosamprenavir ).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on 3-hydroxytetrahydrofuran at TCI Europe, accessed on January 4, 2017.
↑ ^a ^b ^c data sheet 3-Hydroxytetrahydrofuran from Sigma-Aldrich , accessed on January 4, 2017 ( PDF ).
^ M. Pariselle: Sur quelques dérivés du butanetriol-1.2.4 . In: Comptes rendus de l'Académie des sciences . No. 149, 1910, pp. 295-298. PDF .
↑ Vishnu K. Tandon, Albert M. Van Leusen, Hans Wynberg: Synthesis of enantiomerically pure (S) - (+) - 3-hydroxytetrahydrofuran, and its (R) -enantiomer, from malic or tartaric acid . In: The Journal of Organic Chemistry . tape 48 , no. 16 , August 1, 1983, pp. 2767-2769 , doi : 10.1021 / jo00164a027 .
↑ Venkata Mandava, et al .: Preparation of fosamprenavir calcium . US Pat. Appl., 20110224443 (2011).

[TCI-1] ↑ ^a ^b ^c ^d ^e ^f Entry on 3-hydroxytetrahydrofuran at TCI Europe, accessed on January 4, 2017.

[Sigma-2] ta sheet 3-Hydroxytetrahydrofuran from Sigma-Aldrich , accessed on January 4, 2017 ( PDF ).

[3] M. Pariselle: Sur quelques dérivés du butanetriol-1.2.4 . In: Comptes rendus de l'Académie des sciences . No. 149, 1910, pp. 295-298. PDF .

[4] Vishnu K. Tandon, Albert M. Van Leusen, Hans Wynberg: Synthesis of enantiomerically pure (S) - (+) - 3-hydroxytetrahydrofuran, and its (R) -enantiomer, from malic or tartaric acid . In: The Journal of Organic Chemistry . tape 48 , no. 16 , August 1, 1983, pp. 2767-2769 , doi : 10.1021 / jo00164a027 .

[5] Venkata Mandava, et al .: Preparation of fosamprenavir calcium . US Pat. Appl., 20110224443 (2011).