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
Identifiers
CAS Number	107-88-0 ; 6290-03-5 (R) ; 24621-61-2 (S) ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1731276; 1718944 (R); 1718943 (S)
ChEBI	CHEBI:52683 ;
ChEMBL	ChEMBL1231503 ;
ChemSpider	7608 ; 553103 (R) ; 394191 (S) ;
DrugBank	DB02202 ;
ECHA InfoCard	100.003.209
EC Number	203-529-7;
E number	E1502 (additional chemicals)
Gmelin Reference	2409; 2493173 (R); 1994384 (S)
KEGG	D10695 ;
MeSH	1,3-Butylene+glycol
PubChem CID	7896; 637497 (R); 446973 (S);
RTECS number	EK0440000;
UNII	3XUS85K0RA ;
CompTox Dashboard (EPA)	DTXSID8026773 ;
	InChI InChI=1S/C4H10O2/c1-4(6)2-3-5/h4-6H,2-3H2,1H3 Key: PUPZLCDOIYMWBV-UHFFFAOYSA-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). verify (what is ?) Infobox references

1,3-Butanediol is an organic compound with the formula CH₃CH(OH)CH₂CH₂OH, not to be confused with 1,4 Butanediol. With two alcohol functional groups, the molecule is classified as a diol. The compound without the R (or D) designation is racemic, which is what has been used in most studies before 2023. The compound is a colorless, bittersweet, water-soluble liquid. It is one of four common structural isomers of butanediol.^[1]^[2]^[3] It is used in grape flavoring,^[4] and as a precursor to some antibiotics.^[5]

^ Gräfje H, Körnig W, Weitz HM, Reiß W, Steffan G, Diehl, et al. (2000). "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_455. ISBN 9783527306732.
^ "1,3 Butylene Glycol". Parchem Fine & Specialty Chemicals.
^ Dymsza HA (November 1975). "Nutritional application and implication of 1,3-butanediol". Federation Proceedings. 34 (12): 2167–2170. PMID 1102338.
^ Dymsza HA. Nutritional application and implication of 1,3-butanediol. Fed Proc. 1975 Nov;34(12):2167-70 PMID 1102338
^ Guo X, Gao Y, Liu F, Tao Y, Jin H, Wang J, et al. (June 2023). "A short-chain carbonyl reductase mutant is an efficient catalyst in the production of (R)-1,3-butanediol". Microbial Biotechnology. 16 (6): 1333–1343. doi:10.1111/1751-7915.14249. PMC 10221522. PMID 36946330.

[Ullmann-1] Gräfje H, Körnig W, Weitz HM, Reiß W, Steffan G, Diehl, et al. (2000). "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_455. ISBN 9783527306732.

[2] "1,3 Butylene Glycol". Parchem Fine & Specialty Chemicals.

[3] Dymsza HA (November 1975). "Nutritional application and implication of 1,3-butanediol". Federation Proceedings. 34 (12): 2167–2170. PMID 1102338.

[4] Dymsza HA. Nutritional application and implication of 1,3-butanediol. Fed Proc. 1975 Nov;34(12):2167-70 PMID 1102338

[5] Guo X, Gao Y, Liu F, Tao Y, Jin H, Wang J, et al. (June 2023). "A short-chain carbonyl reductase mutant is an efficient catalyst in the production of (R)-1,3-butanediol". Microbial Biotechnology. 16 (6): 1333–1343. doi:10.1111/1751-7915.14249. PMC 10221522. PMID 36946330.

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