1,6-Hexanediol

1,6-Hexanediol
Names
	Preferred IUPAC name Hexane-1,6-diol
	Other names Hexamethylene glycol; 1,6-Dihydroxyhexane; 1,6-Hexylene glycol; Hexamethylenediol; HDO
Identifiers
CAS Number	629-11-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:43078 ;
ChEMBL	ChEMBL458616 ;
ChemSpider	13839416 ;
DrugBank	DB02210 ;
ECHA InfoCard	100.010.068
EC Number	211-074-0;
PubChem CID	12374;
RTECS number	MO2100000;
UNII	ZIA319275I ;
CompTox Dashboard (EPA)	DTXSID1027265 ;
	InChI InChI=1S/C6H14O2/c7-5-3-1-2-4-6-8/h7-8H,1-6H2 Key: XXMIOPMDWAUFGU-UHFFFAOYSA-N ;
	SMILES OCCCCCCO;
Properties
Chemical formula	C6H14O2
Molar mass	118.176 g·mol−1
Density	0.967
Melting point	42 °C (108 °F; 315 K)
Boiling point	250 °C (482 °F; 523 K)
Solubility in water	500g/L
Solubility	soluble in ethanol and acetone, slightly soluble in diethyl ether, insoluble in benzene.
Hazards
Flash point	102 °C (216 °F; 375 K)
	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

1,6-Hexanediol is an organic compound with the formula (CH₂CH₂CH₂OH)₂. It is a colorless water-soluble solid.^[3]

History and synthesis

W. H. Perkin Jr. and his graduate student Edward Haworth first prepared the compound in 1894 during their research on cyclohexane. They boiled 1,6-dibromohexane (which they were also the first to synthesize) with dilute potassium carbonate solution and named the product hexamethylene glycol.^[4]

1,6-Hexanediol is industrially made by the hydrogenation of adipic acid or its esters.^[3]^[5] Laboratory preparation could be achieved by reduction of adipates with lithium aluminium hydride, although this method is impractical on a commercial scale.

Properties

As 1,6-hexanediol contains hydroxyl groups, it undergoes the typical chemical reactions of alcohols such as dehydration, substitution, and esterification. Oxidation with pyridinium chlorochromate gives adipaldehyde.^[6]

Dehydration of 1,6-hexanediol gives oxepane, 2-methyltetrahydropyran and 2-ethyltetrahydrofuran. Corresponding thiophene and pyrrolidone can be made by reacting 1,6-hexanediol with hydrogen sulfide and ammonia respectively.^[7]

Uses

1,6-Hexanediol is widely used for industrial polyester and polyurethane production..^[3]

1,6-Hexanediol can improve the hardness and flexibility of polyesters as it contains a fairly long hydrocarbon chain. In polyurethanes, it is used as a chain extender, and the resulting modified polyurethane has high resistance to hydrolysis as well as mechanical strength, but with a low glass transition temperature.

It is also an intermediate to acrylics as a crosslinking agent, e.g. hexanediol diacrylate.^[3] Unsaturated polyester resins have also been made from 1,6-hexanediol, along with styrene, maleic anhydride and fumaric acid.^[7]

Uses to study biomolecular condensates

1,6-Hexanediol has been used to characterize biomolecular condensates. The material properties of condensates can be examined to determine if they are solid or liquid condensates. 1,6-Hexanediol has been reported to interfere with weak hydrophobic protein-protein or protein-RNA interactions that comprise liquid condensates. 1,6-Hexanediol has been reported to dissolve liquid but not solid condensates.^[8] 2,5-Hexanediol and 1,4-butanediol have been observed to have minimal effect on behavior of disorderd proteins as compared to 1,6-hexanediol.^[9]^[10]

Safety

1,6-Hexanediol^[11] has low toxicity and low flammability, and is generally considered as safe. It is not irritating to skin, but may irritate the respiratory tract or mucous membranes. Dust or vapor of the compound can irritate or damage the eyes.^[1]

References

^ ^a ^b Chemicals and reagents 2008-2010, Merck
^ CRC Handbook of Chemistry and Physics, 87th Edition
^ ^a ^b ^c ^d Peter Werle; Marcus Morawietz; Stefan Lundmark; Kent Sörensen; Esko Karvinen; Juha Lehtonen (2008). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2. ISBN 978-3527306732.
^ Haworth, E.; Perkin, W. H. (1894). "Hexamethylene dibromide and its action on sodium and on ethylic sodio-malonate". Journal of the Chemical Society, Transactions. 65 (0): 591–602. doi:10.1039/CT8946500591. ISSN 0368-1645.
^ Lazier, W. A.; Hill, J. W.; Amend, W. J. (1939). "Hexamethylene glycol". Org. Synth. 19: 48. doi:10.15227/orgsyn.019.0048.
^ Corey, E.J.; Suggs, J.William (1975). "Pyridinium Chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds". Tetrahedron Letters. 16 (31): 2647–2650. doi:10.1016/s0040-4039(00)75204-x.
^ ^a ^b BASF intermediates, BASF
^ Kroschwald, Sonja; Maharana, Shovamayee; Simon, Alberti (2017-05-22). "Hexanediol: a chemical probe to investigate the material properties of membrane-less compartments". Matters. doi:10.19185/matters.201702000010. ISSN 2297-8240.
^ Kato, Masato; McKnight, Steven L. (2018-06-20). "A Solid-State Conceptualization of Information Transfer from Gene to Message to Protein". Annual Review of Biochemistry. 87: 351–390. doi:10.1146/annurev-biochem-061516-044700. ISSN 1545-4509. PMID 29195049. S2CID 28314614.
^ Franco, Hector L.; Nagari, Anusha; Kraus, W. Lee (2015-04-02). "TNFα signaling exposes latent estrogen receptor binding sites to alter the breast cancer cell transcriptome". Molecular Cell. 58 (1): 21–34. doi:10.1016/j.molcel.2015.02.001. ISSN 1097-4164. PMC 4385449. PMID 25752574.
^ Solutions, Navux Commerce. "1,6 Hexanediol (Cas 629-11-8) - Bulk Specialty Chemical Supplier & distributor". www.parchem.com. Retrieved 2024-06-27.

[Merck-1] Chemicals and reagents 2008-2010, Merck

[CRC-2] CRC Handbook of Chemistry and Physics, 87th Edition

[Ull-3] Peter Werle; Marcus Morawietz; Stefan Lundmark; Kent Sörensen; Esko Karvinen; Juha Lehtonen (2008). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2. ISBN 978-3527306732.

[4] Haworth, E.; Perkin, W. H. (1894). "Hexamethylene dibromide and its action on sodium and on ethylic sodio-malonate". Journal of the Chemical Society, Transactions. 65 (0): 591–602. doi:10.1039/CT8946500591. ISSN 0368-1645.

[5] Lazier, W. A.; Hill, J. W.; Amend, W. J. (1939). "Hexamethylene glycol". Org. Synth. 19: 48. doi:10.15227/orgsyn.019.0048.

[6] Corey, E.J.; Suggs, J.William (1975). "Pyridinium Chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds". Tetrahedron Letters. 16 (31): 2647–2650. doi:10.1016/s0040-4039(00)75204-x.

[BASF-7] BASF intermediates, BASF

[8] Kroschwald, Sonja; Maharana, Shovamayee; Simon, Alberti (2017-05-22). "Hexanediol: a chemical probe to investigate the material properties of membrane-less compartments". Matters. doi:10.19185/matters.201702000010. ISSN 2297-8240.

[9] Kato, Masato; McKnight, Steven L. (2018-06-20). "A Solid-State Conceptualization of Information Transfer from Gene to Message to Protein". Annual Review of Biochemistry. 87: 351–390. doi:10.1146/annurev-biochem-061516-044700. ISSN 1545-4509. PMID 29195049. S2CID 28314614.

[10] Franco, Hector L.; Nagari, Anusha; Kraus, W. Lee (2015-04-02). "TNFα signaling exposes latent estrogen receptor binding sites to alter the breast cancer cell transcriptome". Molecular Cell. 58 (1): 21–34. doi:10.1016/j.molcel.2015.02.001. ISSN 1097-4164. PMC 4385449. PMID 25752574.

[11] Solutions, Navux Commerce. "1,6 Hexanediol (Cas 629-11-8) - Bulk Specialty Chemical Supplier & distributor". www.parchem.com. Retrieved 2024-06-27.

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