111-31-9 Usage
Description
1-Hexanethiol is a colorless liquid with an unpleasant odor, characterized by a burnt fat, sulfurous, meaty, and fatty scent. It has a melting point of -81°C and a boiling point of 152-153°C, with a density of 0.838 g cm-3 at 25°C. 1-Hexanethiol is known for its strong and distinctive aroma, which can be detected at very low concentrations.
Uses
1. Used in Chemical Synthesis:
1-Hexanethiol is used as an intermediate in the synthesis of various chemicals, particularly in the rubber processing industry. Its thiol-based properties make it a versatile compound for creating new materials and products.
2. Used in Gold Nanoparticle Functionalization:
1-Hexanethiol can be mixed with 4-mercaptophenol to functionalize gold nanoparticles (AuNPs), which are then used as chemi-resistive sensors. This application takes advantage of the compound's ability to form stable bonds with metal surfaces.
3. Used as a Protective Coating for Copper Surfaces:
1-Hexanethiol forms a protective coating on copper surfaces, shielding them from oxidative reactions and contaminating layers. This coating can be effectively removed by an annealing step in inert N2, providing a clean Cu surface.
4. Used as a Thiol-based Ligand in Thin Film Solar Cells:
1-Hexanethiol serves as a thiol-based ligand with potential applications as a semiconducting material in thin film solar cells. Its properties contribute to the development of more efficient and sustainable energy solutions.
5. Used in Tuning Electrical Characteristics of Carbon Nanotube Transistors:
1-Hexanethiol is utilized to tune the electrical characteristics in networked carbon nanotube field-effect transistors, enhancing their performance and functionality in various electronic applications.
6. Used in Flavor and Fragrance Industry:
1-Hexanethiol is known for its distinct burnt fat, sulfurous, and meaty aroma, with taste threshold values ranging from 0.05 to 1.0 ppm. It is used in the flavor and fragrance industry to create charred pork skin, slightly bitter, lactonic fatty nuances, and roasted, burnt fat and coffee notes. It is also reported to be found in cooked chicken, beef, and pork, adding depth and complexity to their flavors.
Reactivity Profile
1-Hexanethiol is incompatible with oxidizing agents, strong acids and strong bases, alkali metals, and nitric acid. Can react with water, steam or acids to produce toxic and flammable vapors. Reacts violently with powerful oxidizing agents such as calcium hypochlorite(Ca(OCl)2) to generate SOx. Reacts with hydrides to form flammable H2 gas; reacts with halogenated hydrocarbons to yield HX. Reacts exothermically with aldehydes. Emits toxic compounds of sulfur when when heated to decomposition.
Hazard
Combustible.
Check Digit Verification of cas no
The CAS Registry Mumber 111-31-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 111-31:
(5*1)+(4*1)+(3*1)+(2*3)+(1*1)=19
19 % 10 = 9
So 111-31-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H14S/c1-2-3-4-5-6-7/h7H,2-6H2,1H3
111-31-9Relevant articles and documents
A practical, one-step synthesis of primary thiols under mild and neutral conditions using bis(triorganotin) sulfides
Gingras,Harpp
, p. 1397 - 1400 (1990)
Thiols are obtained from primary organic halides and bis(triaryl/alkyltin) sulfides in the presence of fluoride ion in CH3CN/H2O at 20°C. This simple one-step methodology involving fluorodestannylation is carried out under mild and neutral conditions, in sharp contrast to virtually all known methods. Some attempts at utilizing triorganotin and triorganogermanium mercaptans for the same purpose are reported.
Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides
Luo, Jie,Rauch, Michael,Avram, Liat,Ben-David, Yehoshoa,Milstein, David
supporting information, p. 21628 - 21633 (2021/01/11)
Direct hydrogenation of thioesters with H2 provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex without additives. Various thioesters were fully hydrogenated to the corresponding alcohols and thiols with excellent tolerance for amide, ester, and carboxylic acid groups. Thiocarbamates and thioamides also undergo hydrogenation under similar conditions, substantially extending the application of hydrogenation of organosulfur compounds.
Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols
Maurya, Chandra Kant,Mazumder, Avik,Gupta, Pradeep Kumar
supporting information, p. 1184 - 1188 (2017/07/03)
In this paper we report an efficient and mild procedure for the conversion of organic thiocyanates to thiols in the presence of phosphorus pentasulfide (P2S5) in refluxing toluene. The method avoids the use of expensive and hazardous transition metals and harsh reducing agents, as required by reported methods, and provides an attractive alternative to the existing methods for the conversion of organic thiocyanates to thiols.
A rhodium(i)-oxygen adduct as a selective catalyst for one-pot sequential alkyne dimerization-hydrothiolation tandem reactions
Kleinhans, George,Guisado-Barrios, Gregorio,Liles, David C.,Bertrand, Guy,Bezuidenhout, Daniela I.
supporting information, p. 3504 - 3507 (2016/03/04)
An air-stable rhodium(i)-oxygen adduct featuring a CNC-pincer ligand, based on 1,2,3-triazol-5-ylidenes, catalyzes the homo-dimerization and hydrothiolation of alkynes, affording the gem-enyne and α-vinyl sulfide isomers, respectively, with excellent selectivity. A one-pot stepwise strategy allows the selective catalytic preparation of non-symmetric bis-vinyl sulfides, as well as the alkyne dimerization-hydrothiolation tandem reactions.
