Hexadecanethiol

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1-Hexadecanethiol is a chemical compound from the group of thiols. Its chemical formula is C
16
H
34
S
.[1][2]

Hexadecanethiol
Names
Preferred IUPAC name
Hexadecane-1-thiol
Other names
1-hexadecanethiol; hexadecyl mercaptan, 1-mercaptohexadecane, cetyl mercaptan
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.952 Edit this at Wikidata
UNII
  • InChI=1S/C16H34S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3
    Key: ORTRWBYBJVGVQC-UHFFFAOYSA-N
  • CCCCCCCCCCCCCCCCS
Properties
C16H34S
Molar mass 258.51 g·mol−1
Appearance Colorless liquid
Density 0,85 g/cm3
Melting point 18–20 °C (64–68 °F; 291–293 K)
Boiling point 334 °C (633 °F; 607 K)
Insoluble
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
Flash point 135 °C (275 °F; 408 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis

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1-Hexadecanethiol can be obtained by reacting 1-bromohexadecane with thiourea.

Properties

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1-Hexadecanethiol is a combustible colorless liquid with an unpleasant odor, which is practically insoluble in water.[3]

Applications

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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.[4]

Toxicology and safety

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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.

References

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  1. ^ "1-Hexadecanethiol". Sigma Aldrich. sigmaaldrich.com. Retrieved 9 June 2017.
  2. ^ "1-Hexadecanethiol". NIST. webbook.nist.gov. Retrieved 9 June 2017.
  3. ^ 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.
  4. ^ Desmyter, Etienne A.; Ferrell, William J.; Garces., Antonio (July 1976). "Synthesis and properties of 35S, 14C and 3H labeled S-alkyl glycerol ethers and derivatives" (PDF). Chemistry and Physics of Lipids. 16 (4): 276–284. doi:10.1016/0009-3084(76)90022-0. hdl:2027.42/21737. PMID 949825.