Hexadecanethiol
{{Chembox
| ImageFile = 1-hexadecaanthiol t.png
| ImageSize = 200px
| ImageAlt =
| PIN = Hexadecane-1-thiol
| OtherNames = 1-hexadecanethiol; hexadecyl mercaptan, 1-mercaptohexadecane, cetyl mercaptan
| Section1 = {{Chembox Identifiers
| CASNo = 2917-26-2
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QR98QIO1QL
| PubChem = 18015
| ChemSpiderID = 17019
| EINECS =
| SMILES = CCCCCCCCCCCCCCCCS
| StdInChI= 1S/C16H34S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3
| StdInChIKey= ORTRWBYBJVGVQC-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=16|H=34|S=1
| Appearance = Colorless liquid
| Density = 0,85 g/cm3
| Solubility = Insoluble
| MeltingPtC = 18-20
| BoilingPtC = 334
| VaporPressure =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = WARNING
| HPhrases =
| PPhrases =
| FlashPtC = 135
| AutoignitionPt =
}}
}}
1-Hexadecanethiol is a chemical compound from the group of thiols. Its chemical formula is {{chem|C|16|H|34|S}}.{{cite web|title=1-Hexadecanethiol|url=http://www.sigmaaldrich.com/catalog/product/aldrich/674516?lang=en®ion=RU|website=Sigma Aldrich|publisher=sigmaaldrich.com|accessdate=9 June 2017}}{{cite web|title=1-Hexadecanethiol|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=2917-26-2|website=NIST|publisher=webbook.nist.gov|accessdate=9 June 2017}}
Synthesis
1-Hexadecanethiol can be obtained by reacting 1-bromohexadecane with thiourea.
Properties
1-Hexadecanethiol is a combustible colorless liquid with an unpleasant odor, which is practically insoluble in water.CRC Handbook of Chemistry and Physics, 90. Edition, CRC Press, Boca Raton, Florida, 2009, {{ISBN|978-1-4200-9084-0}}, Section 3, Physical Constants of Organic Compounds, p. 3-306.
Applications
1-Hexadecanethiol is used as a synthesis chemical. The compound is also used for the production of nanoparticles and hydrophobic self-assembling monolayers. The high affinity of the thiol group to the elements of the copper group causes the thiols to spontaneously deposit in a high-order layer when a corresponding metal of a 1-hexadecanethiol solution is exposed.{{cite journal|last1=Desmyter|first1=Etienne A.|last2=Ferrell|first2=William J.|last3=Garces.|first3=Antonio|title=Synthesis and properties of 35S, 14C and 3H labeled S-alkyl glycerol ethers and derivatives|journal=Chemistry and Physics of Lipids|date=July 1976|volume=16|issue=4|pages=276–284|doi=10.1016/0009-3084(76)90022-0|pmid=949825 |url=https://deepblue.lib.umich.edu/bitstream/2027.42/21737/1/0000130.pdf|hdl=2027.42/21737|hdl-access=free}}
Toxicology and safety
The substance decomposes upon combustion with the formation of toxic gases, including sulfur oxides. It reacts violently with strong oxidizing agents, acids, reducing agents, and metals.