1-Dodecanethiol is a colourless liquid organic compound, with a characteristic odour. Soluble in methanol, ether, acetone, benzene, ethyl acetate, insoluble in water.
Dodecyl mercaptan is a poymerization inhibitor added to polyurethane resins and Neoprene glues for use, e.g., in the shoe industry.
1-Dodecanethiol is used in the preparation of hydrophobic or mixed self-assembled monolayers. It is also employed as a chain transfer agent for radical polymerization. Further, it is utilized as a polymerization inhibitor in polyurethane and neoprene adhesives, which finds application in the footwear industry. In addition to this, it acts as a protein regenerating agent used for the regeneration of native proteins from mercuribenzoate.
1-Dodecanethiol can be used for the synthesis of thiol-stabilized metal nanoparticles (NPs), such as gold nanoparticles and silver nanoparticles, which have been produced for use as catalysts, electronic devices, fillers, sensors and active components in composite materials, and other applications.
This molecule is used for the production of hydrophobic SAMs. It can also be used in mixed SAMs to give a hydrophobic background and act as a spacer to move other functional groups or domains farther apart.
Preparation of 1-dodecanethiol: 1-Bromododecane, thiourea and 95% ethanol are heated to reflux reaction, then sodium hydroxide solution is added and heated. After the reaction is finished, cooled and left to stratify, the oil layer is the crude thiol. The crude product is washed with water, dried, distilled, and distilled under reduced pressure, which is 1-dodecanethiol.
Oily colorless liquid with a mild skunk odor. Freezing point 19°F.
Air and moisture sensitive. Insoluble in water. Reacts vigorously with water or steam.
1-Dodecanethiol is incompatible with bases, oxidizing agents, reducing agents and alkali metals. Easily oxidized to disulfide.
1-Dodecanethiol is irritating to skin, eyes, and mucous membranes. Ingestion may cause nausea. Repeated skin exposure can cause dermatitis and may produce a sensitizing effect. It is very toxic to aquatic life with long lasting effects.
Special Hazards of Combustion Products: Poisonous and irritating gases (e.g., sulfur dioxide) are generated in fires.
Dry it with CaO for several days, then distil it from CaO. [Beilstein 1 IV 1851.]
