7210-80-2

Basic information

• Product Name: Neopentylphenylsulfide
• Synonyms: Neopentylphenylsulfide;[(2,2-Dimethylpropyl)thio]benzene
• CAS NO: 7210-80-2
• Molecular Formula: C₁₁H₁₆S
• Molecular Weight: 326.5386
• Mol File: 7210-80-2.mol
• Article Data: 17

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Neopentylphenylsulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Neopentylphenylsulfide(7210-80-2)
• EPA Substance Registry System: Neopentylphenylsulfide(7210-80-2)

Safety Data

• Hazardous Substances Data: 7210-80-2(Hazardous Substances Data)

Upstream product

• 2346-07-8 neopentyl tosylate 
• 930-69-8 sodium thiophenolate 
• 882-33-7 diphenyldisulfane 
• 108-98-5 thiophenol 
• 212077-64-0 neopentyloxy(diphenyl)-λ⁶-sulfanenitrile 
• 1203470-67-0 CpCr[(XylNCMe)2CH](CH₂CMe₃) 
• 15501-33-4 neopentyl iodide 
• 630-17-1 2,2-dimethylpropyl bromide 
• 100-68-5 methyl-phenyl-thioether 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 677-22-5 tert-butylmagnesium chloride 
• 16427-42-2 methanesulfonic acid 2,2-dimethyl-propyl ester 
• 10284-47-6 chloro(2,2-dimethylpropyl)mercury 
• 75-84-3 2,2-dimethyl-propanol-1 

Downstream Products

• 10269-15-5 neopentyl phenyl sulphone 
• 72653-49-7 1-chloro-2,2-dimethylpropyl phenyl sulphide 
• 1365610-83-8 (R)-(+)-neopentyl phenyl sulfoxide 
• 100-68-5 methyl-phenyl-thioether 
• 17414-00-5 (1-Acetoxy-2,2-dimethyl-propyl)-phenylsulfid 
• 119704-14-2 (E)-2-(2,2-dimethylpropylidene)cyclohexanone 
• 72653-52-2 2-(1-phenylthio-2,2-dimethylpropyl)cyclohexanone 
• 72653-53-3 2-(2,2-dimethylpropyl)cyclohexanone 
• 10335-98-5 neopentyl phenyl sulfoxide 

Relevant articles and documents

Alkylation of Nitropyridines via Vicarious Nucleophilic Substitution

Electrophilic nitropyridines react with sulfonyl-stabilized carbanions to give products of C-H alkylation via vicarious nucleophilic substitution. The process consists of formation of the Meisenheimer-type adduct followed by base-induced β-elimination of the sulfinic acid (e.g., PhSO2H). Mechanistic studies reveal that in the latter step alkyl substituent and adjacent nitro group tend to planarize for effective stabilization of benzyl anion, and thus, adduct of hindered isopropyl carbanion remains stable toward elimination for steric reasons.

Transalkylation of alkyl aryl sulfides with alkylating agents

The reaction of methyl iodide with tert-butylphenylsulfide in DMF leads to a transalkylation that produces methylphenylsulfide. This transalkylation reaction was further studied by 1H NMR spectroscopy. The polarity of the solvent, the electron density on the sulfur atom, and the strength of the alkylating agent (MeI, EtI, BuI, dimethyl sulfate, or dimethyl carbonate) played important roles in the reaction. The suggested mechanism of the reaction involves the formation of a dialkyl aryl sulfonium salt that subsequently eliminates the radical. This mechanism was supported by the observation of higher conversion rates for compounds with more branched alkyl groups on the sulfur atom, which may lead to the formation of more stable radicals.

Investigation of steric and electronic effects in the copper-catalysed asymmetric oxidation of sulfides

Steric and electronic effects in the copper-catalysed asymmetric oxidation of aryl benzyl, aryl alkyl and alkyl benzyl sulfides have been investigated. The presence of an aryl group directly attached to the sulfur is essential to afford sulfoxides with high enantioselectivities, with up to 97% ee for 2-naphthyl benzyl sulfoxide, the highest enantioselectivity achieved to date for copper-catalysed asymmetric sulfoxidation. In contrast, the benzyl substituent can be replaced by sterically comparable groups with no effect on enantioselectivity. Copper-mediated oxidation of substituted aryl benzyl sulfides display modest steric and electronic effects resulting in comparable or lower enantioselectivities to those obtained with the unsubstituted benzyl phenyl sulfide.