1,2,4-Butanetriol

1,2,4-Butanetriol
IUPAC name Butane-1,2,4-triol
Other names 1,2,4-Butanetriol 1,2,4-Trihydroxybutane Triol 124 2-Deoxyerthritol
Identifiers
CAS number	3068-00-6 Y
ChemSpider	17287 Y
EC number	221-323-5
RTECS number	EK7176000
Jmol-3D images	Image 1 Image 2
SMILES OCC(O)CCO OCCC(O)CO
InChI InChI=1S/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2 Y Key: ARXKVVRQIIOZGF-UHFFFAOYSA-N Y InChI=1/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2 Key: ARXKVVRQIIOZGF-UHFFFAOYAQ
Properties
Molecular formula	C4H10O3
Molar mass	106.12 g mol−1
Density	1.19
Boiling point	190–191 °C (18 torr)
Hazards
R-phrases	R36
S-phrases	S24/25
NFPA 704	1 2 0
Flash point	112 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,2,4-Butanetriol is a clear or slightly yellow, odorless, hygroscopic, flammable, viscous liquid. It is an alcohol with three hydrophilic alcoholic hydroxyl groups. It is similar to glycerol and erythritol. It is chiral, with two possible enantiomers.

1,2,4-Butanetriol is used in the manufacture of butanetriol trinitrate (BTTN), an important military propellant.

1,2,4-Butanetriol is also used as a precursor for two cholesterol-lowering drugs, Crestor and Zetia, which are derived from D-3,4-dihydroxybutanoic acid, by using 3-hydroxy-gamma-butyrolactone as a chiral synthon Niu, W (2003). "Microbial synthesis of the energetic material precursor 1,2,4-butanetriol". Am. Chem. Soc. 125 (43): 12998–12999. doi:10.1021/ja036391+. http://pubs.acs.org/doi/abs/10.1021/ja036391%2B.  "Biosynthetic Pathways". http://www.frostchemlab.com/biosynthetic-pathways.htm. Retrieved 24 November 2010. . It is as one of the monomers for manufacture of some polyesters and as a solvent.

1,2,4-Butanetriol can be prepared synthetically by several different methods such as hydroformylation of glycidol and subsequent reduction of the product, sodium borohydride reduction of esterified malic acid, or catalytic hydrogenation of malic acid. However, of an increasing importance is the biotechnological synthesis using genetically engineered Escherichia coli and Pseudomonas fragi bacteria.