1,5-Pentanediol

1,5-Pentanediol[1]
IUPAC name pentane-1,5-diol
Other names Pentylene glycol Pentamethylene glycol 1,5-Dihydroxypentane
Identifiers
CAS number	111-29-5 Y
PubChem	8105
ChemSpider	13839441 Y
ChEMBL	CHEMBL448289 Y
Jmol-3D images	Image 1 Image 2
SMILES OCCCCCO C(CCO)CCO
InChI InChI=1S/C5H12O2/c6-4-2-1-3-5-7/h6-7H,1-5H2 Y Key: ALQSHHUCVQOPAS-UHFFFAOYSA-N Y InChI=1/C5H12O2/c6-4-2-1-3-5-7/h6-7H,1-5H2 Key: ALQSHHUCVQOPAS-UHFFFAOYAE
Properties
Molecular formula	C5H12O2
Molar mass	104.14758
Density	0.994 g/mL at 25 °C
Melting point	−18 °C; 0 °F; 255 K
Boiling point	242 °C; 468 °F; 515 K
Solubility in water	Miscible
Hazards
NFPA 704	1 2 0
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

1,5-Pentanediol is the organic compound with the formula HOCH₂CH₂CH₂CH₂CH₂OH. Like other diols, this viscous colourless liquid is used as plasticizer and also forms polyesters that are used as emulsifying agents and resin intermediates.^[2]

Preparation

1,5-Pentanediol is manufactured by hydrogenation of glutaric acid and its derivatives.^[3] It can also be prepared by hydrogenation of furfural followed by hydrogenolysis of the substituted tetrahydrofuran.^[4]

Contamination of Bindeez

A toy called Bindeez (Aqua Dots in North America) was recalled by the distributor in November 2007 because of the unauthorized substitution of 1,5-pentanediol with 1,4-butanediol. The toy consists of small beads that stick to each other upon sprinkling with water. 1,4-Butanediol, which when ingested is metabolized to gamma-hydroxybutyric acid, was detected by GC-MS.^[5][6] ChemNet China lists the price of 1,4-butanediol at between about US$1,350–2,800/tonne, while the price for 1,5-pentanediol is about US$9,700/tonne.^[7]

References