1,6-Hexanediol: Difference between revisions

| Watchedfields = changed

| verifiedrevid = 456366461

| PIN = Hexane-1,6-diol

|Section1={{Chembox Identifiers

| CASNo = 629-11-8

| CASNo_Ref = {{cascite|correct|CAS}}

| PubChem = 12374

| EC_number = 211-074-0

| RTECS = MO2100000

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 458616

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 43078

| UNII_Ref = {{fdacite|correct|FDA}}

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|Section2={{Chembox Properties

| C=6 | H=14 | O=2

| Appearance =

| Density = 0.967

| MeltingPtC = 42

| BoilingPtC = 250

| Solubility = 500g/L <ref name="Merck">''Chemicals and reagents'' 2008-2010, Merck</ref>

| SolubleOther = soluble in [[ethanol]] and [[acetone]], slightly soluble in [[diethyl ether]], insoluble in [[benzene]].<ref name="CRC">CRC Handbook of Chemistry and Physics, 87th Edition</ref>

|Section3={{Chembox Hazards

| MainHazards =

| FlashPtC = 102

| AutoignitionPt =

'''1,6-Hexanediol''' is an [[organic compound]] with the formula (CH₂CH₂CH₂OH)₂. It is a colorless water-soluble solid.<ref name=Ull>{{Ullmann|author1=Peter Werle|author2=Marcus Morawietz|author3=Stefan Lundmark|author4=Kent Sörensen|author5=Esko Karvinen|author6=Juha Lehtonen|title=Alcohols, Polyhydric|year=2008|doi=10.1002/14356007.a01_305.pub2}}</ref>

1,6-Hexanediol is prepared by the [[hydrogenation]] of [[adipic acid]] or its esters.<ref name=Ull/><ref>{{cite journal|title=Hexamethylene glycol|first1=W. A. |last1=Lazier|first2=J. W.|last2=Hill|first3=W. J.|last3=Amend|journal=Org. Synth.|year=1939|volume=19|page=48|doi=10.15227/orgsyn.019.0048}}</ref> Laboratory preparation could be achieved by reduction of [[Adipic_acid#Adipate_salts_and_esters|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 [[alcohol (chemistry)|alcohol]]s such as [[dehydration reaction|dehydration]], [[Substitution reaction|substitution]], [[esterification]]. Oxidation with [[pyridinium chlorochromate]] gives [[adipaldehyde]].<ref>{{cite journal |doi=10.1016/s0040-4039(00)75204-x |title=Pyridinium Chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds |date=1975 |last1=Corey |first1=E.J. |last2=Suggs |first2=J.William |journal=Tetrahedron Letters |volume=16 |issue=31 |pages=2647–2650 }}</ref>

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.<ref name="BASF">BASF intermediates, BASF</ref>

1,6-Hexanediol is widely used for industrial [[polyester]] and [[polyurethane]] production..<ref name=Ull/>

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. [[1,6-Hexanediol diacrylate|hexanediol diacrylate]].<ref name=Ull/> [[Unsaturated polyester resin]]s have also been made from 1,6-hexanediol, along with [[styrene]], [[maleic anhydride]] and [[fumaric acid]].<ref name="BASF" />

== Uses to study biomolecular condensates ==

1,6-Hexanediol has been used to characterize [[Biomolecular condensate|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.<ref>{{cite journal |last1=Kroschwald |first1=Sonja |last2=Maharana |first2=Shovamayee |last3=Simon |first3=Alberti |date=2017-05-22 |title=Hexanediol: a chemical probe to investigate the material properties of membrane-less compartments |journal=Matters |language=en |doi=10.19185/matters.201702000010 |issn=2297-8240|doi-access=free }}</ref> [[2,5-Hexanediol]] and [[1,4-Butanediol|1,4-butanediol]] have been observed to have minimal effect on behavior of disorderd proteins as compared to 1,6-hexanediol.<ref>{{cite journal |last1=Kato |first1=Masato |last2=McKnight |first2=Steven L. |date=2018-06-20 |title=A Solid-State Conceptualization of Information Transfer from Gene to Message to Protein |url=https://pubmed.ncbi.nlm.nih.gov/29195049/?dopt=Abstract |journal=Annual Review of Biochemistry |volume=87 |pages=351–390 |doi=10.1146/annurev-biochem-061516-044700 |issn=1545-4509 |pmid=29195049|s2cid=28314614 }}</ref><ref>{{cite journal |last1=Franco |first1=Hector L. |last2=Nagari |first2=Anusha |last3=Kraus |first3=W. Lee |date=2015-04-02 |title=TNFα signaling exposes latent estrogen receptor binding sites to alter the breast cancer cell transcriptome |journal=Molecular Cell |volume=58 |issue=1 |pages=21–34 |doi=10.1016/j.molcel.2015.02.001 |issn=1097-4164 |pmc=4385449 |pmid=25752574}}</ref>

==Safety==

1,6-Hexanediol<ref>{{Cite web |last=Solutions |first=Navux Commerce |title=1,6 Hexanediol (Cas 629-11-8) - Bulk Specialty Chemical Supplier & distributor |url=https://www.parchem.com/chemical-supplier-distributor/1-6-hexanediol-008442 |access-date=2024-06-27 |website=www.parchem.com}}</ref> 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.<ref name="Merck" />

{{DEFAULTSORT:Hexanediol, 1, 6-}}

[[Category:Alkanediols]]