4163-79-5

Usage

Chemical compound

2,6-DIMETHYLTHIOANISOLE

Physical state

Colorless to pale yellow liquid

Odor

Strong, sweet, slightly fruity

Uses

Flavoring agent in food and beverage industry, fragrance ingredient in perfumes and cosmetics

Characteristics

Volatile sulfur compound contributing to truffle aroma

Safety

Considered safe for consumption and use in controlled amounts

InChI:InChI=1/C9H12S/c1-7-5-4-6-8(2)9(7)10-3/h4-6H,1-3H3

Upstream product

• 576-22-7 2-Bromo-m-xylene 
• 74-88-4 methyl iodide 
• 15475-27-1 potassium diphenylphosphine 
• 118-72-9 2,6-dimethylbenzene-1-thiol 
• 124-38-9 carbon dioxide 
• 2905-17-1 bis(2,6-dimethylphenyl)disulfide 
• 624-92-0 Dimethyldisulphide 
• 4143-34-4 Monothiophosphorsaeure-O,O-dimethylester-S-(2,6-dimethyl-phenylester) 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 74266-21-0 (3-Methyl-2-methylsulfanyl-phenyl)-acetic acid 
• 648906-19-8 4-bromo-2,6-dimethylthioanisole 
• 97416-12-1 methyl 2,6-dimethylphenyl sulphone 
• 110275-25-7 {Pd(MeS(C₆H₄Me₂-2,6))2Cl₂} 
• 40669-05-4 2,6-dimethylphenyl methyl sulphoxide 
• 60147-10-6 2,6-Bis(brommethyl)methylthiobenzol 

Relevant academic research and scientific papers

Reduction of CO2 with NaBH4/I2 for the Conversion of Thiophenols to Aryl Methyl Sulfides

We report a tandem reaction to realize reduction of carbon dioxide with thiophenols to generate aryl methyl sulfides under the NaBH4/I2 system with 18-crown-6 as the solvent. Thiophenols bearing electron-donating and electron-withdrawing groups are feasible in this reaction. Controlled experiment results indicate that 18-crown-6 plays a critical role in six-electron reduction of carbon dioxide.

Reactivity of dimeric cyclopalladated complexes with an (sp3)C-Pd bond toward KPPh2

Abstract Reactions of KPPh2 with dimeric C,N, C,P and C,S cyclopalladated complexes (CPCs) 1a-g containing an (sp3)C-Pd bond were investigated. The CPCs used in the study were obtained from D-camphor O-methyloxime (a), l-fenchone O-methyloxime (b), 4,4-dimethyl-2-phenyl-2-oxazoline (c), 8-methylquinoline (d), trimesitylphosphine (e), tri(O-tolyl)phosphine (f) and 2,6-dimethylthioanisole (g). The dichloro-bridged CPCs 1a,b,d,f,g and the diacetato-bridged analog μ-OAc-1d reacted with 4.5 equiv. of KPPh2 at room temperature in THF to give either phosphines 2a,b or phosphine oxides 8d,f,g in 20-51% yield. Complexes 1a,b,d reacted with 1 equiv. of KPPh2 to produce the corresponding μ-chloro-μ-diphenylphosphido-CPCs 3a,b,d in 33-56% yield. In the reaction of CPC 1c with 4.5 equiv. of KPPh2, complex 4c with two PPh2 bridging ligands was isolated in 36% yield. Structures of phosphines 2a,b, phosphine oxides 8a,d,f,g as well as complexes 3a,b,d and 4c were confirmed by 1H, 13C{1H} and 31P{1H} NMR spectroscopy.

Reactions of Cyclopalladated Compounds. Part 21. Various Examples of Sulphur-assisted Intramolecular Palladation of Aryl and Alkyl Groups

The cyclopalladation reactions of several sulphur-containing ligands have been investigated.The thioethers benzyl methyl sulphide, methyl naphthyl sulphide, 2,6-dimethylphenyl methyl sulphide, and neopentyl sulphide have been metallated by palladium acetate in acetic acid at either aryl or alkyl carbon atoms to afford, after reaction with lithium chloride in acetone, dimeric chloride-bridged cyclopalladated complexes in moderate (22percent) to good (81percent) yields.In these products each metal is part of a five-membered ring.The same reaction with 2-biphenyl methyl sulphide afforded a dimeric complex containing a six-membered cyclopalladated ring through palladation of the ortho position of the biphenyl group. 4,4'-Dimethoxythiobenzophenone and N,N,N',N'-tetramethyl-thiourea have been palladated by using a ligand-exchange reaction with 2> in the presence of stoicheiometric amounts of trifluoroacetic acid.This afforded good yields of dimeric palladocyclic complexes through the metallation of a carbon ortho to the thioketone, or of a methyl group of the thiourea, respectively.With 1,3-bis(methylthiomethyl)benzene this latter reaction, by metallation on the 2 position of the aryl ring, afforded excellent yields of a monomeric compound in which both sulphur atoms are co-ordinated to the palladium centre.