Hexadecanethiol

Hexadecanethiol
Names
	IUPAC name hexadecane-1-thiol
	Other names 1-hexadecanethiol; hexadecane-1-thiol, 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 pictograms
GHS 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.

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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.

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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.