2917-26-2

Basic information

• Product Name: 1-Hexadecanethiol
• Synonyms: n-Hexadecyl mercaptan
• CAS NO: 2917-26-2
• Molecular Formula: C₁₆H₃₄S
• Molecular Weight: 258.50616
• EINECS: 220-846-6
• Mol File: 2917-26-2.mol

Chemical Properties

• Melting Point: 18-20℃
• Boiling Point: 335.2 °C at 760 mmHg
• Flash Point: 101.7 °C
• Appearance: Colorless liquid or white solid
• Density: 0.842 g/cm³
• Vapor Pressure: 0.000237mmHg at 25°C
• Refractive Index: 1.46
• Water Solubility: INSOLUBLE
• CAS DataBase Reference: 1-Hexadecanethiol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Hexadecanethiol(2917-26-2)
• EPA Substance Registry System: 1-Hexadecanethiol(2917-26-2)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36:
• Safety Statements: S26:
• Hazardous Substances Data: 2917-26-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1-Hexadecanethiol is used as a chemical intermediate for the production of surfactants, lubricants, and plasticizers, due to its ability to react with other compounds to form useful products.
Used in Nanotechnology and Materials Science:
1-Hexadecanethiol is used as a surface modifier in the preparation of self-assembled monolayers, for its capacity to form stable and organized structures on surfaces, which is crucial in nanotechnology and materials science applications.
Used in Corrosion Inhibition:
1-Hexadecanethiol is used as a component in the formulation of corrosion inhibitors, leveraging its properties to protect materials from degradation and corrosion.
Used in Organic Transformations and Reactions:
1-Hexadecanethiol is used as a chemical reagent in certain organic transformations and reactions, where its thiol group can participate in various chemical processes, such as redox reactions or the formation of disulfide bonds.

InChI:InChI=1/C16H34S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3

Upstream product

• 36653-82-4 1-Hexadecanol 
• 544-77-4 1-iodohexadecane 
• 629-73-2 1-Hexadecene 
• 7783-06-4 hydrogen sulfide 
• 194550-80-6 N-acetylglycine hexadecyl thioester 
• 112-39-0 hexadecanoic acid methyl ester 
• 66143-73-5 n-cetyl thiocyanate 
• 106-95-6 allyl bromide 
• 629-79-8 palmitonitrile 
• 64-19-7 acetic acid 
• 194550-81-7 glycine hexadecylamide 
• 112-82-3 hexadecanyl bromide 
• 17356-08-0 thiourea 
• 5424-93-1 dimethyl-dithiocarbamic acid hexadecyl ester 

Downstream Products

• 6140-88-1 hexadecane-1-sulfonic acid 
• 1561-75-7 dihexadecyl disulfide 
• 2307-33-7 n-Hexadecylthiopalmitat 
• 105543-68-8 2-Benzyloxy-3-hexadecylsulfanyl-propan-1-ol 
• 127542-51-2 3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 2,3,6-tri-O-benzoyl-4-O-<6-O-acetyl-2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside 
• 127542-23-8 3-(hexadecylthio)-2-<(hexadecylthio)methyl>propyl 6-O-acetyl-3-deoxy-3C-methyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 154-23-4 catechin 
• 38775-38-1 1-hexadecanesulfonyl chloride 
• 121-33-5 vanillin 

Relevant articles and documents

Proximity effects in monolayer films: Kinetic analysis of amide bond formation at the air-water interface using 1H NMR spectroscopy

The kinetics of amide bond formation in a monolayer film has been studied by proton NMR spectroscopy. Compression of a hexadecyl thioester of N-acetyl glycine (1) and a hexadecyl amide of glycine (2) at the air-water interface produces a single dipeptide product (4) that remains at the surface once formed. Extraction of the reaction mixture from the interface, followed by 1H NMR spectroscopy, provides quantitative data on the rate of product formation. The kinetics of this reaction was examined as a function of surface pressure, subphase pH, and temperature. The monolayer provides an effective molarity for the reaction of ～500 M as compared to the bimolecular reaction of 1 and 4 in chloroform solution. The first-order rate constant for the reaction of 1 and 2 in the monolayer is less than 70-fold slower than kcat for condensation of the first amide bond in the enzymatic synthesis of the cyclic antibiotic gramicidin S by gramicidin S synthetase. Activation energies of the reaction were extracted from the temperature dependence of the rate constants of the reaction and are 9.9 ± 1.0 and 2.1 ± 0.2 kcal/mol for the chloroform solution and monolayer reactions, respectively. The pKa of 2 in the monolayer was estimated to be ～0.5 pKa units lower than that of related amines in solution. The lower pKa at the interface as compared to that in solution may be ascribed to increased electrostatic repulsion at the interface relative to solution. The rate of reaction in the monolayer was also followed by monitoring changes in surface area as a function of time. The rate constant for the reaction of 1 and 4 as determined by changes in surface area differs significantly from the rate determined by NMR. The results indicate that measurements of surface area versus time may yield erroneous rate constants for reactions in monolayers.

Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols

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.

Hydrodeoxygenation of methyl palmitate over sulfided Mo/Al 2O3, CoMo/Al2O3 and NiMo/Al 2O3 catalysts

The catalytic properties of sulfided Mo/Al2O3, CoMo/Al2O3 and NiMo/Al2O3 catalysts in the hydrodeoxygenation of methyl palmitate as a model compound for triglyceride feedstock were studied at 300°C and 3.5 MPa in the batch reactor using n-tetradecane, m-xylene and hydrotreated straight-run gas oil (HT-SRGO). The comparison of catalyst's performance in n-tetradecane allowed us to see that the sulfided Mo/Al2O3, CoMo/Al 2O3 and NiMo/Al2O3 catalysts revealed the same rate of the methyl palmitate conversion but the rate of the intermediate oxygenates conversion decreased in order: CoMoS/Al 2O3 > NiMoS/Al2O3 > MoS 2/Al2O3. A mixture of linear saturated and unsaturated C15 and C16 hydrocarbons was produced when the oxygenates were fully consumed. The main products obtained over the Mo/Al 2O3 and CoMo/Al2O3 catalysts were C16 hydrocarbons (C16/C15-16.1 and 2.79, respectively); however, C15 hydrocarbons were preferentially formed over the NiMo/Al2O3 catalyst (C16/C 15-0.65), highlighting the different contributions of the hydrodeoxygenation (HDO) and decarboxylation/decarbonylation (DeCOx) pathways during the hydroconversion of methyl palmitate over these catalysts. Investigating the solvent's influence on the activity of the CoMo/Al 2O3 and NiMo/Al2O3 catalysts in the methyl palmitate HDO revealed that the reaction rate was decreased in the following order: n-tetradecane > HT-SRGO > m-xylene. The aromatic compounds did not retard the methyl palmitate transformation, but inhibited the conversion of the intermediate oxygenates. Decreased C16/C 15 ratios were observed over both catalysts when m-xylene was used as the reaction medium instead of n-tetradecane.

Water effects on SmI2 reductions: A novel method for the synthesis of alkyl thiols by SmI2-promoted reductions of sodium alkyl thiosulfates and alkyl thiocyanates

Water as a cosolvent has significant improving effect on the reductivity of SmI2 in the reduction of sodium alkyl thiosulfates and alkyl thiocyanates. A new method for synthesis of alkyl thiols by SmI 2/THF/H2O system has been developed.

One-pot synthetic method of allyl sulfides: Samarium-induced allyl bromide mediated reduction of alkyl thiocyanates and diaryl disulfides in methanolic medium

A convenient synthetic method of allyl sulfides by the treatment of alkyl thiocyanates or diaryl disulfides with Sm and allyl bromide in methanol has been developed.