1,2,4-butanetriol

Structural formula
	Structural formula without stereochemistry
General
Surname	1,2,4-butanetriol
other names	1,2,4-trihydroxybutane
Molecular formula	C 4 H 10 O 3
Brief description	yellow liquid
External identifiers / databases
ECHA InfoCard	100.019.385
PubChem	18302
Wikidata	Q4187980
properties
Molar mass	106.12 g mol −1
Physical state	liquid
density	1.185 g cm −3
Melting point	−20 ° C
boiling point	190–191 ° C at 24 hPa
solubility	miscible with water
Refractive index	1.473 (20 ° C)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	23,000 mg kg −1 ( LD 50 , mouse , oral )
	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

1,2,4-Butanetriol is a chemical compound from the group of alcohols . The compound is chiral with two possible enantiomers .

Extraction and presentation

1,2,4-butanetriol can be prepared by hydration of 2-butyne-1,4-diol using mercury catalysts are obtained. For reasons of hygiene, this implementation is unsuitable for large-scale production. It is more advantageous if butene-2-diol-1,4-epoxide is hydrogenated to 1,2,4-butanetriol. The epoxide is obtained by reacting butenediol with hydrogen peroxide . The preparation by catalytic hydrogenation of malic acid esters over a copper- containing catalyst is also possible .

properties

1,2,4-Butanetriol is a moisture-sensitive, very difficult to ignite, hygroscopic yellow liquid that is miscible with water.

use

1,2,4-Butanetriol is used as a starting material for the synthesis of a number of quaternary ammonium lipids. It is also used in the synthesis of (-) - γ-amino-8-hydroxybutyric acid (GABOB), anti-epileptic and antihypertensive drugs . It is also used to produce 3-hydroxytetrahydrofuran .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry for CAS no. 3068-00-6 in the GESTIS substance database of the IFA , accessed on July 23, 2014(JavaScript required) .
↑ ^a ^b ^c data sheet (±) -1,2,4-butanetriol, technical, ≥90% (GC) from Sigma-Aldrich , accessed on July 23, 2014 ( PDF ).
↑ Patent DE19890128 : Process for the preparation of 1,2,4-butane triol. Inventor: MULLER HERBERT; MESCH WALTER; BROELLOS KLAUS. ‌
↑ 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 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry for CAS no. 3068-00-6 in the GESTIS substance database of the IFA , accessed on July 23, 2014(JavaScript required) .

[Sigma-2] ta sheet (±) -1,2,4-butanetriol, technical, ≥90% (GC) from Sigma-Aldrich , accessed on July 23, 2014 ( PDF ).

[3] Patent DE19890128 : Process for the preparation of 1,2,4-butane triol. Inventor: MULLER HERBERT; MESCH WALTER; BROELLOS KLAUS. ‌

[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 .