16241-02-4

Basic information

• Product Name: O-(4-methylphenyl) N,N-dimethylthiocarbamate
• Synonyms: O-(4-methylphenyl) N,N-dimethylthiocarbamate
• CAS NO: 16241-02-4
• Molecular Weight: 195.285
• Mol File: 16241-02-4.mol

Chemical Properties

• CAS DataBase Reference: O-(4-methylphenyl) N,N-dimethylthiocarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: O-(4-methylphenyl) N,N-dimethylthiocarbamate(16241-02-4)
• EPA Substance Registry System: O-(4-methylphenyl) N,N-dimethylthiocarbamate(16241-02-4)

Safety Data

• Hazardous Substances Data: 16241-02-4(Hazardous Substances Data)

Upstream product

• 74415-50-2 N,N-dimethylthiocarbamoyl thiocyanate 
• 1121-70-6 sodium 4-methylphenoxide 
• 937-63-3 p-Tolyl chlorothionoformate 
• 124-40-3 dimethyl amine 
• 106-44-5 p-cresol 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 19384-35-1 O-(4-Tolyl)-S-(N,N-dimethylthiocarbamoyl)-dithiocarbonat 
• 137-26-8 Thiram 

Downstream Products

• 7322-85-2 S-(4-methylphenyl) N,N-dimethylthiocarbamate 
• 106-45-6 para-thiocresol 
• 1152899-15-4 C₁₃H₁₀Cl₂OS₂ 
• 33257-85-1 6-methyl-3,4-diphenyl-2H-chromen-2-one 

Relevant articles and documents

Iron(II)/Persulfate Mediated Newman-Kwart Rearrangement

Herein, we report that iron(II)/ammonium persulfate in aqueous acetonitrile mediates the Newman-Kwart rearrangement of O-aryl carbamothioates. Electron-rich substrates react rapidly under moderate heating to afford the rearranged products in excellent yie

Electrochemically Catalyzed Newman-Kwart Rearrangement: Mechanism, Structure-Reactivity Relationship, and Parallels to Photoredox Catalysis

The facilitation of redox-neutral reactions by electrochemical injection of holes and electrons, also known as "electrochemical catalysis", is a little explored approach that has the potential to expand the scope of electrosynthesis immensely. To systematically improve existing protocols and to pave the way toward new developments, a better understanding of the underlying principles is crucial. In this context, we have studied the Newman-Kwart rearrangement of O-arylthiocarbamates to the corresponding S-aryl derivatives, the key step in the synthesis of thiophenols from the corresponding phenols. This transformation is a particularly useful example because the conventional method requires temperatures up to 300 °C, whereas electrochemical catalysis facilitates the reaction at room temperature. A combined experimental-quantum chemical approach revealed several reaction channels and rendered an explanation for the relationship between the structure and reactivity. Furthermore, it is shown how rapid cyclic voltammetry measurements can serve as a tool to predict the feasibility for specific substrates. The study also revealed distinct parallels to photoredox-catalyzed reactions, in which back-electron transfer and chain propagation are competing pathways.

An Electrocatalytic Newman-Kwart-type Rearrangement

An electrochemical approach toward rearrangement of O-aryl thiocarbamates to the corresponding S-aryl thiocarbamates is presented. The protocol requires only catalytic amounts of electric charge and allows for operation at room temperature. The electrolys

Base-Promoted Synthesis of O -Aryl/Alkyl N, N -Dimethylthiocarbamates Starting from Inexpensive and Environmentally Benign Disulfide

A series of O -aryl (alkyl) N, N -dimethylthiocarbamates were synthesized in good yields (70-77%) by reacting substituted phenols or alkyl alcohol with inexpensive, stable, and environmentally benign tetramethylthiuram disulfide (TMTD) in the presence of NaH. By avoiding use of the toxic and corrosive N, N -dialkylthiocarbamoyl chloride, the method provides a green and facile preparation for some important precursors of potentially biologically reactive compounds.

Ambient-Temperature Newman-Kwart Rearrangement Mediated by Organic Photoredox Catalysis

The Newman-Kwart rearrangement is perhaps the quintessential method for the synthesis of thiophenols from the corresponding phenol. However, the high thermal conditions required for the rearrangement of the requisite O-aryl carbamothioates often leads to decomposition. Herein, we present a general strategy for catalysis of O-aryl carbamothioates to S-aryl carbamothioates using catalytic quantities of a commercially available organic single-electron photooxidant. Importantly, this reaction is facilitated at ambient temperatures.

Palladium-catalyzed intramolecular oxidative C-H sulfuration of aryl thiocarbamates

A palladium-catalyzed intramolecular C-H bond sulfuration reaction of aryl thiocarbamates has been developed. This strategy provides a new route to benzo[d][1,3]oxathiol-2-ones with tolerance of a wide range of substituents. Mechanistic studies suggested

Ago-allosteric modulators of human glucagon-like peptide 2 receptor

Glucagon-like peptide 2 (GLP-2) is an intestinotropic peptide that binds to GLP-2 receptor (GLP-2R), a class-B G protein-coupled receptor (GPCR). Few synthetic agonists have been reported so far for class-B GPCRs. Here, we report the first scaffold compounds of ago-allosteric modulators for human GLP-2R, derived from methyl 2-{[(2Z)-2-(2,5-dichlorothiophen-3-yl)-2-(hydroxyimino) ethyl]sulfanyl}benzoate (compound 1).

The Newman-Kwart rearrangement re-evaluated by microwave synthesis

The Newman-Kwart rearrangement (NKR) has been re-evaluated by microwave heating. Microwave technology has proven to be ideal for investigating this high temperature rearrangement and facilitated the confirmation of many aspects of this valuable reaction.

Application of microreactor technology in process development

The microreactor technology is an efficient tool for kilogram-scale syntheses in continuous mode and is particularly effective for hazardous reactions that do not allow scale-up in conventional reactors. Applications to several classes of reactions including highly exothermic reactions, high-temperature reactions, reactions with unstable intermediates, and reactions involving hazardous reagents are described herein.

Potassium fluoride on alumina: Synthesis of O-aryl N,N-dimethylthiocarbamates and their rearrangement into S-aryl N,N-dimethylthiocarbamates under microwave irradiation

A series of O-aryl N,N-dimethyl thiocarbamates have been prepared by the reaction of dimethylthiocarbamoyl chloride with phenols absorbed on potassium fluoride on alumina. The rearrangement of O-aryl N,N-dimethylthiocarbamate into S-aryl N,N-dimethylthiocarbamate under microwave irradiation was also studied. The use of conductive support like graphite or silicon carbide allow these rearrangements although the O-aryl N,N-dimethylthiocarbamates have very low dielectric lost.