1,5-Pentanediol

1,5-Pentanediol is the organic compound with the formula HO(CH₂)₅OH. Like other diols, this viscous colourless liquid is used as plasticizer and also forms polyesters that are used as emulsifying agents and resin intermediates.^[3]

1,5-Pentanediol^[1]

Names
Preferred IUPAC name Pentane-1,5-diol
Other names Pentamethylene glycol 1,5-Dihydroxypentane
Identifiers
CAS Number	111-29-5 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL448289 Y
ChemSpider	13839441 Y
ECHA InfoCard	100.003.505
EC Number	203-854-4
PubChem CID	8105
UNII	07UXZ0SCST Y
CompTox Dashboard (EPA)	DTXSID2041256
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
SMILES OCCCCCO
Properties
Chemical 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
GHS labelling:[2]
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
NFPA 704 (fire diamond)	2 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Synthesis and reactions

1,5-Pentanediol is produced by hydrogenation of glutaric acid and its derivatives.^[4] It can also be prepared by hydrogenolysis of tetrahydrofurfuryl alcohol.^[5] 1,4-Pentadiene can be prepared from 1,5-pentadiol via the diacetate.^[6]

Contamination of Bindeez

See also: 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.^[7][8] 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.^[9]

References

1. 1,5-Pentanediol at Sigma-Aldrich
2. "1,5-Pentanediol". pubchem.ncbi.nlm.nih.gov.
3. Merck Index, 11th Edition, 7073.
4. Werle, P.; Morawietz, M. "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305. ISBN 978-3527306732.
5. Nakagawa, Yoshinao; Tomishige, Keiichi (2012). "Production of 1,5-Pentanediol from Biomass via Furfural and Tetrahydrofurfuryl Alcohol". Catalysis Today. 195: 136–143. doi:10.1016/j.cattod.2012.04.048.
6. R. E. Benson, B. C. McKusick, Oliver Grummitt, E. P. Budewitz, C. C. Chudd (1958). "1,4-Pentadiene". Organic Syntheses. 38: 78. doi:10.15227/orgsyn.038.0078.{{cite journal}}: CS1 maint: multiple names: authors list (link)
7. Wang, L. (2007-11-09). "Industrial Chemical Sullies Popular Children's Toy". Chemical & Engineering News.
8. Griffiths, J. (2008). "Government and Society: Scientific sleuthing: how GC/MS uncovered toy danger". Analytical Chemistry. 80 (1): 6. doi:10.1021/ac085987i.
9. "Mom: Chemical-laced toy made son 'drunk'". USA Today. Associated Press. 2007-11-09.