1,6-Hexanediol

changed changed 456366461 1,6-Hexanediol.svg skin-invert-image 200px Hexane-1,6-diol Hexamethylene glycol; 1,6-Dihydroxyhexane; 1,6-Hexylene glycol; Hexamethylenediol; HDO 629-11-8 correct CAS 12374 211-074-0 MO2100000 correct chemspider 13839416 correct EBI 458616 correct EBI 43078 correct FDA ZIA319275I correct drugbank DB02210 OCCCCCCO correct chemspider 1S/C6H14O2/c7-5-3-1-2-4-6-8/h7-8H,1-6H2 correct chemspider XXMIOPMDWAUFGU-UHFFFAOYSA-N 6 14 2 0.967 42 250 500g/L Chemicals and reagents 2008-2010, Merck soluble in ethanol and acetone, slightly soluble in diethyl ether, insoluble in benzene.CRC Handbook of Chemistry and Physics, 87th Edition 102 1,6-Hexanediol is an organic compound with the formula (CH2CH2CH2OH)2. It is a primary alcohol, and appears as a colorless water-soluble solid.Peter Werle Marcus Morawietz Stefan Lundmark Kent Sörensen Esko Karvinen Juha Lehtonen Alcohols, Polyhydric 2008 10.1002/14356007.a01_305.pub2 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 heated a suspension of 1,6-dibromohexane, (which they were also the first to synthesize) in dilute aqueous potassium carbonate solution. They named resulting colorless syrup hexamethylene glycol.Haworth E. Perkin W. H. 1894 Hexamethylene dibromide and its action on sodium and on ethylic sodio-malonate https://books.google.com/books?id=Deo2AAAAYAAJ&pg=PA598 Journal of the Chemical Society, Transactions en 65 591–602 10.1039/CT8946500591 0368-1645 1,6-Hexanediol is industrially made by the hydrogenation of adipic acid or its esters.Hexamethylene glycol W. A. Lazier J. W. Hill W. J. Amend Org. Synth. 1939 19 48 10.15227/orgsyn.019.0048 free 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.10.1016/s0040-4039(00)75204-x Pyridinium Chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds 1975 Corey E.J. Suggs J.William Tetrahedron Letters 16 31 2647–2650 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.BASF intermediates, BASF Uses 1,6-Hexanediol is widely used for industrial polyester and polyurethane production. 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. Unsaturated polyester resins have also been made from 1,6-hexanediol, along with styrene, maleic anhydride and fumaric acid. 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.Kroschwald Sonja Maharana Shovamayee Simon Alberti 2017-05-22 Hexanediol: a chemical probe to investigate the material properties of membrane-less compartments Matters en 10.19185/matters.201702000010 16 July 2025 2297-8240 free 2,5-Hexanediol and 1,4-butanediol have been observed to have minimal effect on behavior of disordered proteins as compared to 1,6-hexanediol.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 10.1146/annurev-biochem-061516-044700 1545-4509 29195049 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 10.1016/j.molcel.2015.02.001 1097-4164 4385449 25752574 Safety 1,6-HexanediolSolutions Navux Commerce 1,6 Hexanediol (Cas 629-11-8) - Bulk Specialty Chemical Supplier & distributor https://www.parchem.com/chemical-supplier-distributor/1-6-hexanediol-008442 2024-06-27 www.parchem.com 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. References Category:Alkanediols