10312. 1,4-Butanediol

Nomenclature

CAS number: 110-63-4
1,4-Butylene glycol; 1,4-dihydroxybutane; tetramethylene glycol; BDO.
C4H10O2; mol wt 90.12.
C 53.31%, H 11.18%, O 35.51%.

Description and references

Commercial chemical used in the manufacture of polymer fibers and plastics. Metabolically converted to the CNS depressant, γ-hydroxybutyrate, (GHB) q.v. Prepn from N,N′-dinitrobutanediyldiamine: M. P. J. Dekkers, Recl. Trav. Chim. Pays-Bas 9, 92 (1890); from 4-benzyloxybutan-1-ol: W. R. Kirner, G. H. Richter, J. Am. Chem. Soc. 51, 2503 (1929) DOI. LC-MS/MS determn in urine: M. Wood et al., J. Chromatogr. A 1056, 83 (2004) DOI PubMed. Toxicological profile: R. D. Irwin, J. Appl. Toxicol. 26, 72 (2006) DOI PubMed. Clinical pharmacokinetics, metabolism, and toxicology: D. Thai et al., Clin. Pharm. Ther. 81, 178 (2007) DOI PubMed. Review of abuse as substitute for GHB: R. B. Palmer, Toxicol. Rev. 23, 21-31 (2004) DOI PubMed. Review of industrial prepns and uses: M. L. Morgan, Chem. Ind. (London) 3, 166-168 (1997); T. Haas et al., Appl. Catal. A 280, 83-88 (2005) DOI.

Chemical structure

Properties

Colorless, viscous liquid. mp 19-19.5°. bp 230°. d420 1.0171. nD20 1.4467. Sol in water, DMSO, acetone, 95% ethanol. LD50 in albino rats (mg/kg): 1000 i.p.; 1550 orally (Irwin).

Caution

When ingested, may cause dizziness, alcohol-like inebriation, sedation. Symptoms of overexposure include vomiting, myoclonus, respiratory depression, coma, or death (Thai).

Use

Industrial solvent; intermediate in organic synthesis; polymer feedstock.