3775-12-0

Basic information

• Product Name: 3,4-dimethyl-1,2,5-thiadiazole-1,1-dioxide
• Synonyms: 3,4-dimethyl-1,2,5-thiadiazole-1,1-dioxide
• CAS NO: 3775-12-0
• Molecular Weight: 146.17
• Mol File: 3775-12-0.mol

Chemical Properties

• CAS DataBase Reference: 3,4-dimethyl-1,2,5-thiadiazole-1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dimethyl-1,2,5-thiadiazole-1,1-dioxide(3775-12-0)
• EPA Substance Registry System: 3,4-dimethyl-1,2,5-thiadiazole-1,1-dioxide(3775-12-0)

Safety Data

• Hazardous Substances Data: 3775-12-0(Hazardous Substances Data)

Upstream product

• 7803-58-9 SULFAMIDE 
• 431-03-8 dimethylglyoxal 

Downstream Products

• 1620097-51-9 (R)-3-(4-methoxyphenyl)-3,4-dimethyl-2,3-dihydro-1,2,5-thiadiazole-1,1-dioxide 
• 1620097-52-0 (R)-3-(4-chlorophenyl)-3,4-dimethyl-2,3-dihydro-1,2,5-thiadiazole-1,1-dioxide 

Relevant articles and documents

3,4-Disubstituted derivatives of 1,2,5-thiadiazole 1,1-dioxide. Ethanol addition reactions and electroreduction of 3-methyl-4-phenyl and 3,4-dimethyl derivatives in acetonitrile and ethanol solvents

3-Methyl-4-phenyl-1,2,5-thiadiazole 1,1-dioxide (TMP), as well as 3,4-dimethyl-1,2,5-thiadiazole 1,1-dioxide (TMM), react with ethanol (EtOH), which adds to one of their C=N double bonds. The equilibrium constants for the addition reaction are measured in mixed acetonitrile (ACN) - EtOH solvents by means of UV spectroscopy in the case of TMP, and by 13C NMR spectroscopy in the case of TMM, since TMM presents only terminal UV absorption. Both equilibrium constants are also estimated through cyclic voltammetry (CV) experiments. In the case of TMP, the ethanol molecule adds to the C=N bond located on the methyl-substituted side of the substrate, according to 13C NMR spectroscopy and CV results. The electroreduction characteristics of the substrates and their ethanol addition products are studied using CV techniques in ACN, EtOH, and ACN-EtOH solvent mixtures. The radical anion formed by the first electron transfer to TMM is unstable and decomposes rapidly while that corresponding to TMP undergoes a relatively slow homogeneous second-order reaction with the substrate (k = 3 × 102 M-1 s-1). The equilibrium constant for EtOH addition and the voltammetric properties of the substrates are compared with those of the previously studied 3,4-diphenyl derivative (TPP).

Solvent-Free Condensation Reactions to Synthesize Five-Membered Heterocycles Containing the Sulfamide Fragment

We report a study of the solvent-free condensation reaction of 1,2-dicarbonyl compounds with sulfamide catalyzed by a Keggin-type acid (H3PMo12O40·nH2O, MPA) to obtain 3,4-disubstituted 1,2,5-thiadiazole 1,1-dioxide derivatives. Some reactions were also performed in solution or using nano-sized silica-supported MPA catalyst in order to compare the results under different experimental conditions. Effects of the temperature used for the thermal pretreatment of the catalyst, the reaction temperature, the molar ratios sulfamide/1,2-dicarbonyl compound and MPA/1,2-dicarbonyl compound, and alternative experimental procedures on the yield of the reaction product were investigated. Under suitable experimental conditions eight compounds were obtained in good yields. The catalyst was recycled and reused, but with some loss of its catalytic activity. The presented synthetic method is a simple, clean, and environmentally friendly alternative for synthesizing different 1,2,5-thiadiazole 1,1-dioxide derivatives.

Thiadiazole dioxides as bleach enhancers

Novel bleaches, a method for bleaching substrates using these materials and detergent compositions containing same are reported. The bleaches are thiadiazole dioxides. Substrates such as fabrics may be bleached in an aqueous solution containing the thiadi