1,3-Butanediol

1,3-Butanediol

Names
Preferred IUPAC name Butane-1,3-diol
Other names 1,3-butylene glycol, butane-1,3-diol, or 1,3-dihydroxybutane; Ketohol
Identifiers
CAS Number	107-88-0 Y 6290-03-5 (R) Y 24621-61-2 (S) Y
3D model (JSmol)	Interactive image
Beilstein Reference	1731276 1718944 (R) 1718943 (S)
ChEBI	CHEBI:52683 N
ChEMBL	ChEMBL1231503 N
ChemSpider	7608 Y 553103 (R) Y 394191 (S) Y
DrugBank	DB02202 N
ECHA InfoCard	100.003.209
EC Number	203-529-7
E number	E1502 (additional chemicals)
Gmelin Reference	2409 2493173 (R) 1994384 (S)
KEGG	D10695 N
MeSH	1,3-Butylene+glycol
PubChem CID	7896 637497 (R) 446973 (S)
RTECS number	EK0440000
UNII	3XUS85K0RA Y
CompTox Dashboard (EPA)	DTXSID8026773
InChI InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3 N Key: PUPZLCDOIYMWBV-UHFFFAOYSA-N N
SMILES CC(O)CCO
Properties
Chemical formula	C4H10O2
Molar mass	90.122 g·mol−1
Appearance	Colourless liquid
Density	1.0053 g cm−3
Melting point	−50 °C (−58 °F; 223 K)
Boiling point	204 to 210 °C; 399 to 410 °F; 477 to 483 K
Solubility in water	1 kg dm−3
log P	−0.74
Vapor pressure	8 Pa (at 20 °C)
Refractive index (nD)	1.44
Thermochemistry
Std molar entropy (S⦵298)	227.2 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298)	−501 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298)	−2.5022 MJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319, H413
Precautionary statements	P305+P351+P338
NFPA 704 (fire diamond)	1 1 0
Flash point	108 °C (226 °F; 381 K)
Autoignition temperature	394 °C (741 °F; 667 K)
Related compounds
Related butanediol	1,2-Butanediol 1,4-Butanediol 2,3-Butanediol
Related compounds	2-Methylpentane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

1,3-Butanediol (also 1,3-butylene glycol) is an organic compound with the formula C₄H₁₀O₂ (CH₃CH(OH)CH₂CH₂OH). It is one of four structural isomers of butanediol.

With two alcohol functional groups, the molecule is classified as a secondary alcohol and diol. Without the R (or D) designation, it is racemic. It is a colorless, bittersweet, water-soluble liquid.

1,3-Butanediol is commonly used as a deodorizer and as a solvent for additives that flavor foods. In resin manufacturing, it is a chemical intermediate for making polyurethane and polyesters.

Synthesis

It can be manufactured by the aldol condensation of acetaldehyde, then by catalytic hydrogenation.

Hydrogenation of 3-hydroxybutanal gives 1,3-butanediol:

CH₃CH(OH)CH₂CHO + H₂ → CH₃CH(OH)CH₂CH₂OH

Dehydration of 1,3-butanediol gives 1,3-butadiene:

CH₃CH(OH)CH₂CH₂OH → CH₂=CH-CH=CH₂ + 2 H₂O

Manufactured 1,3-butanediol is flammable.

Occurrence

1,3-Butanediol is present in bell peppers (Capsicum annuum).

Uses and research

It is used as an air freshener, flavor ingredient in foods, animal foods, and in handicrafts. It is recognized as a safe food ingredient in the United States.

1,3-Butanediol is under preliminary research for its potential use in recovery from intense exercise, although its high cost of production is a barrier to general adoption for this purpose.

It is considered to be a potential oral exogenous ketone agent for treating brain mechanisms influencing weight loss in anorexia nervosa.

References