3698-89-3

Basic information

• Product Name: Dodecyl methyl sulfide
• Synonyms: DODECYL METHYL SULFIDE;Heartleaf houtluynia ether;dodecyl(Methyl)sulfane;Dodecyl methyl sulfide 97%;1-(Methylsulfanyl)dodecane;1-Methylthiododecane;Dodecane, 1-(methylthio)-;Dodecyl methyl sulphide
• CAS NO: 3698-89-3
• Molecular Formula: C₁₃H₂₈S
• Molecular Weight: 216.42642
• EINECS: 223-028-7
• Product Categories: sulfide Flavor;Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
• Mol File: 3698-89-3.mol

Chemical Properties

• Melting Point: -2°C(lit.)
• Boiling Point: 110 °C0.2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /Liquid
• Density: 0.816 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0037mmHg at 25°C
• Refractive Index: n20/D 1.4610(lit.)
• CAS DataBase Reference: Dodecyl methyl sulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Dodecyl methyl sulfide(3698-89-3)
• EPA Substance Registry System: Dodecyl methyl sulfide(3698-89-3)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• RIDADR: UN 3334
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3698-89-3(Hazardous Substances Data)

Usage

Uses

Used in Flavoring and Fragrance Industry:
Dodecyl methyl sulfide is used as a flavoring agent and fragrance in the cosmetics and food industries. Its mild, sweet, onion-like aroma is employed to enhance the scent of various products, providing a pleasant and distinctive olfactory experience.
Used in Chemical Production:
Dodecyl methyl sulfide serves as a chemical intermediate in the production of surfactants, lubricants, and other specialty chemicals. Its unique chemical properties make it a valuable component in the synthesis of a wide range of industrial products.
Used in Cosmetics:
In the cosmetics industry, Dodecyl methyl sulfide is used as a fragrance ingredient to add a subtle, pleasant scent to products such as perfumes, lotions, and creams. Its ability to provide a mild, sweet aroma makes it a popular choice for enhancing the sensory appeal of cosmetic products.
Used in Food Industry:
Dodecyl methyl sulfide is also utilized in the food industry as a flavoring agent. Its characteristic onion-like aroma can be used to add depth and complexity to the taste profiles of various food products, contributing to a more enjoyable and appetizing experience for consumers.
Used in Specialty Chemicals:
As a component in the production of specialty chemicals, Dodecyl methyl sulfide plays a crucial role in the development of innovative products with specific applications. Its versatility in chemical reactions and compatibility with other compounds make it an essential intermediate in the synthesis of various chemical products.

InChI:InChI=1/C13H28S/c1-3-4-5-6-7-8-9-10-11-12-13-14-2/h3-13H2,1-2H3

Upstream product

• 143-15-7 1-dodecylbromide 
• 5188-07-8 sodium thiomethoxide 
• 112-52-7 1-chlorododecane 
• 77-78-1 dimethyl sulfate 
• 112-55-0 1-dodecylthiol 
• 17616-89-6 S-dodecyl-S-methyl-sulfodiimide 
• 2667-20-1 potassium methylxanthate 
• 67-56-1 methanol 
• 5418-86-0 tris(methylthio)methane 
• 4292-19-7 1-Iodododecane 
• 624-92-0 Dimethyldisulphide 
• 74-88-4 methyl iodide 
• 26960-77-0 sodium dodecanethiolate 
• 93413-77-5 N,N-didesmethylvenlafaxine 

Downstream Products

• 3079-30-9 methyl dodecyl sulfoxide 
• 56912-64-2 benzyl-dodecyl-methyl sulfonium ; chloride 
• 27268-36-6 toluene-4-sulfonic acid ; dodecyl-dimethyl sulfonium-salt 
• 2749-36-2 S-dodecyl-S-methyl-sulfoximide 
• 17616-89-6 S-dodecyl-S-methyl-sulfodiimide 
• 51186-33-5 dodecyldimethylsulfonium methyl sulfate 
• 18412-81-2 dodecyl-dimethylsulphonium iodide 
• 7560-61-4 1-methylsulfonyldodecane 
• 22161-92-8 1-dodecyl-4-methoxy-benzene 

Relevant articles and documents

Nickel-Catalyzed Negishi-Type Arylation of Trialkylsulfonium Salts

Negishi-type arylation of trialkylsulfonium salts with arylzinc reagents has been accomplished under nickel catalysis. The use of cyclohexanethiol as an additional ligand was found to be particularly important to promote C-S cleavage. The present reaction accommodates one-pot arylation of dialkyl sulfides by combining with S -methylation with MeOTf. Mechanistic experiments suggest that C-S cleavage would proceed via single-electron transfer (SET) to generate the most stable carbon-centered radical and that the thiolate ligand would promote the C-S cleavage and radical recombination step.

Catalytic dehydrogenation of amines to imines and the in-situ reduction of sulfoxides into sulfides

The catalytic acceptorless dehydrogenation of primary amines into imines and H2 represents one of the most important organic transformations, and the in-situ utilization of the generated H2 for chemical reduction reactions has never

B2cat2-Mediated Reduction of Sulfoxides to Sulfides

An efficient and operationally simple method for the reduction of sulfoxides to sulfides has been developed using bis(catecholato)diboron (B2cat2) as a reducing agent. The present method accommodates various functional groups which are generally prone to reduction: halides, alkynes, carbonyls, nitriles, and heterocycles are totally intact, and only sulfoxide moieties undergo reduction chemoselectively. Moreover, the remaining diboron and the resulting boron-containing wastes are readily removable, the practicality of this protocol being thus demonstrated.

Nickel phosphide nanoalloy catalyst for the selective deoxygenation of sulfoxides to sulfides under ambient H2pressure

Exploring novel catalysis by less common, metal-non-metal nanoalloys is of great interest in organic synthesis. We herein report a titanium-dioxide-supported nickel phosphide nanoalloy (nano-Ni2P/TiO2) that exhibits high catalytic activity for the deoxygenation of sulfoxides. nano-Ni2P/TiO2 deoxygenated various sulfoxides to sulfides under 1 bar of H2, representing the first non-noble metal catalyst for sulfoxide deoxygenation under ambient H2 pressure. Spectroscopic analyses revealed that this high activity is due to cooperative catalysis by nano-Ni2P and TiO2. This journal is

A Manganese N-Heterocyclic Carbene Catalyst for Reduction of Sulfoxides with Silanes

The first reduction of sulfoxides catalysed by a well-defined manganese complex is described. A variety of sulfoxides are reduced to the corresponding sulfides in high yields using phenylsilane, diphenylsilane, and the economically feasible 1,1,3,3-tetramethyldisiloxane (TMDS) as reducing agents in the presence of a Mn-NHC complex. The reaction is performed under air and without the need of any additive. The involvement of radicals in the catalytic reaction is probed by spin-trap experiments.

Aminopyridine-Borane Complexes as Hydrogen Atom Donor Reagents: Reaction Mechanism and Substrate Selectivity

Lewis base-borane complexes are shown to be potent hydrogen atom donors in radical chain reduction reactions. Results obtained in 1H, 11B, and 13C NMR measurements and kinetic experiments support a complex reaction mechanism involving the parent borane as well as its initial reaction products as active hydrogen atom donors. Efficient reduction reactions of iodides, bromides, and xanthates in apolar solvents rely on initiator systems generating oxygen-centered radicals under thermal conditions and pyridine-borane complexes carrying solubilizing substituents. In contrast to tin hydride reagents, the pyridine-boranes reduce xanthates faster than the corresponding iodides.

Unprecedented synthesis of iron-NHC complexes by C-H activation of imidazolium salts. Mild catalysts for reduction of sulfoxides

A direct synthesis of bidentate cyclopentadienyl-functionalised NHC-iron(ii) complexes by using imidazolium salts and commercially available Fe3(CO)12 is developed. These well-defined iron-NHC complexes efficiently catalyse the reduction of sulfoxides under mild conditions. Radical scavenging experiments indicate the presence of free radicals in the catalytic reaction. The Royal Society of Chemistry 2012.

Approaching ambient temperatures in 1,2-DCE to deliver efficient intermolecular D?tz benzannulation processes

Conditions have been developed that enable intermolecular D?tz benzannulations to be carried out under extremely mild conditions, using 1,2-DCE as the reaction solvent and without the requirement for any additional reaction promoters. The new protocols, at temperatures close to ambient, have been applied successfully to a range of internal and terminal alkynes with a series of aryl and alkenyl carbene complexes, resulting in good to high yields of the benzannulation products. The developed conditions did, however, return lower benzannulation yields when utilised with the traditionally more troublesome 2-furyl carbene complex. It was found that increased reaction temperatures in 1,2-DCE did deliver high yields for the processes with this heteroaryl species.

Processes for the synthesis of O-desmethylvenlafaxine

The present invention describes processes for the preparation of O-desmethylvenlafaxine and tridesmethylvenlafaxine, which may be used as an intermediate in preparing O-desmethylvenlafaxine.

The syntheses of sulfides by deoxygenation of sulfoxides using Woollins' reagent

Woollins' reagent (WR) acts as a deoxygenation reagent for a wide range of sulfoxides affording the corresponding sulfides in good to excellent yields (up to 99% isolated yield) under mild conditions.