1,2,4-Butanetriol

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1,2,4-Butanetriol
200px
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
EINECS number 221-323-5
RTECS number EK7176000
SMILES OCC(O)CCO
Properties
Molar mass 106.12
Density 1.19
Boiling point

190-191 °C (18 torr)

Hazards
NFPA 704

NFPA 704.svg

1
2
0
 
R-phrases R36
S-phrases S24/25
Flash point 112 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and 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, 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.[1] However, of an increasing importance is the biotechnological synthesis using genetically engineered Escherichia coli and Pseudomonas fragi bacteria.[2]

References

  1. Chemical & Engineering News, May 31, 2004, Volume 82, Number 22, pp. 31-34, "Biomass or Bust" Web version
  2. The State News, Feb. 12, 2004, "Propelling Research" by Meghan Gilbert. = 22196 Web version

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