Hexadecanethiol

Hexadecanethiol
Names
	Preferred IUPAC name Hexadecane-1-thiol
	Other names 1-hexadecanethiol; hexadecyl mercaptan, 1-mercaptohexadecane, cetyl mercaptan
Identifiers
CAS Number	2917-26-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	17019;
ECHA InfoCard	100.018.952
PubChem CID	18015;
UNII	QR98QIO1QL ;
CompTox Dashboard (EPA)	DTXSID6062709 ;
	InChI 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;
	SMILES CCCCCCCCCCCCCCCCS;
Properties
Chemical formula	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)
Solubility in water	Insoluble
Hazards
	GHS labelling:
Pictograms
Signal word	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). Infobox references

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

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.[3]

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.[4]

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.

References

"1-Hexadecanethiol". Sigma Aldrich. sigmaaldrich.com. Retrieved 9 June 2017.
"1-Hexadecanethiol". NIST. webbook.nist.gov. Retrieved 9 June 2017.
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.
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.

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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.

[CRC_HANDBOOK-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.