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  Y
3D model (JSmol)	Interactive image
ChemSpider	17019
ECHA InfoCard	100.018.952
PubChem CID	18015
UNII	QR98QIO1QL  Y
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. "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.