1,4-Butanediol

1,4-Butanediol

Names
IUPAC name Butane-1,4-diol
Other names Tetramethylene glycol
Identifiers
CAS Number	110-63-4 Y
3D model (Jmol)	Interactive image Interactive image
ChEMBL	ChEMBL171623 Y
ChemSpider	13835209 Y
DrugBank	DB01955 Y
ECHA InfoCard	100.003.443
EC Number	203-786-5
RTECS number	EK0525000
UNII	7XOO2LE6G3 Y
InChI InChI=1S/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2 Y Key: WERYXYBDKMZEQL-UHFFFAOYSA-N Y InChI=1/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2
SMILES OCCCCO C(CCO)CO
Properties
Chemical formula	C4H10O2
Molar mass	90.12 g·mol−1
Density	1.0171 g/cm3 (20 °C)
Melting point	20.1 °C (68.2 °F; 293.2 K)
Boiling point	235 °C (455 °F; 508 K)
Solubility in water	Miscible
Solubility in ethanol	Soluble
Magnetic susceptibility (χ)	-61.5·10−6 cm3/mol
Refractive index (nD)	1.4460 (20 °C)
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H302
GHS precautionary statements	P264, P270, P301+312, P330, P501
NFPA 704	1 1 0
Flash point	121 °C (250 °F; 394 K)(open cup)
Autoignition temperature	350 °C (662 °F; 623 K)
Related compounds
Related butanediols	1,2-Butanediol 1,3-Butanediol 2,3-Butanediol
Related compounds	Succinaldehyde Succinic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

1,4-Butanediol, colloquially known as BD, is the organic compound with the formula HOCH₂CH₂CH₂CH₂OH. This colorless viscous liquid is derived from butane by placement of alcohol groups at each end of the chain. It is one of many stable isomers of butanediol.

In its industrial synthesis, acetylene reacts with two equivalents of formaldehyde to form 1,4-butynediol. This type of acetylene-based process is illustrative of what is known as "Reppe chemistry", after German chemist Walter Reppe. Hydrogenation of 1,4-butynediol gives 1,4-butanediol. This route is used by BASF and Ashland/ISP.

LyondellBasell manufactures 1,4-butanediol in a multi-step process without the use of acetylene. First, propylene oxide is converted to allyl alcohol. The allyl alcohol is then hydroformylated to 4-hydroxybutyraldehyde. Hydrogenation of this aldehyde yields 1,4-butanediol.

It is also manufactured on an industrial scale from maleic anhydride in the Davy process, which is first converted to the methyl maleate ester, then hydrogenated. Other routes are from butadiene, allyl acetate and succinic acid.

A biological route to BDO has been commerciallized that uses a genetically modified organism. The biosynthesis proceeds via 4-hydroxybutyrate.