N-Ethyl-o-toluenesulfonamide

• CAS: 1077-56-1
• Catalog Number: ACM1077561-1
• Category: Main Products
• Molecular Weight: 199.27
• Molecular Formula: C9H13NO2S
• Synonyms: Benzenesulfonamide, N-ethyl-2-methyl-;N-Ethyltoluene-2-sulphonamide;Ethyl tosylamide
• Boiling Point: 196 °C
• Melting Point: 344-350℃(lit.)
• Flash Point: 145.7°C
• Density: 1.153 g/cm³
• Appearance: Liquid
• Assay: 0.99
• Packaging: 100 g
• Physical State: Solid
• Refractive Index: 1.526

Case Study

N-Ethyl-o-toluenesulfonamide participates in the synthesis of saccharin derivatives

Xu, Liang, et al. Tetrahedron 62.33 (2006): 7902-7910.

There is a novel and practical method for the preparation of saccharin and saccharin derivatives by oxidation of substituted toluene derivatives via the H5IO6-CrO3 system. This oxidative cyclization method is superior to other methods in terms of both the yield of constructing the saccharin ring system and the amount of waste metals produced. In addition, this method is tolerant to a wide range of functional groups and can easily prepare substituted saccharin derivatives that were previously difficult to synthesize. A variety of biologically important saccharin skeletons and their N-alkyl derivatives were efficiently prepared by chromium(VI) oxide-catalyzed H5IO6 oxidation of N-alkyl-o-methylarenesulfonamides (e.g. N-Ethyl-o-toluenesulfonamide) in acetonitrile. The N-tert-butyl saccharin skeleton can be easily prepared by H5IO6-CrO3 oxidation of N-tert-butyl-o-methylarenesulfonamide in the presence of acetic anhydride. The method for providing novel fluoro- and trifluoromethyl-substituted saccharin skeletons is characterized by two steps, simple workup procedures, single purification, and good overall yields of substituted toluene derivatives.
Competitive oxidation of the a-C-H of the N-alkyl group was observed in the oxidation of several N-alkyl o-toluenesulfonamides. Oxidation of N-methyl o-toluenesulfonamide (1b) afforded N-methyl saccharin (2b) in 35% yield and also afforded saccharin (2a) in 20% yield. Oxidation of N-ethyl o-toluenesulfonamide (1c) afforded N-ethyl saccharin (2c) in only 12% yield. The competitive a-C-H oxidation of N-isopropyl-o-toluenesulfonamide (1d) was more pronounced than that of N-cyclopropyl-o-toluenesulfonamide (1e). However, 2,2,2-trifluoroethyl and tert-butyl groups were able to tolerate the oxidation conditions. Oxidation of N-2,2,2-trifluoroethyl-o-toluenesulfonamide (1f) afforded 94% of the corresponding saccharin derivative 2f at room temperature or reflux. Oxidation of N-tert-butyl o-toluenesulfonamide (1g) also afforded the corresponding N-tert-butyl saccharin (2g) in high yield at room temperature. In addition, the yield of 2 g was slightly improved when acetic anhydride was added to the reaction mixture to maintain anhydrous conditions. Due to the heterogeneous nature of the reaction mixture, acetic anhydride was chosen as the drying agent instead of molecular sieves or other inorganic reagents.

Study of the polar compound N-Ethyl-o-toluenesulfonamide in snowmelt

Maurer, Loïc, et al. Environmental Science & Technology 57.10 (2023): 4143-4152.

The contamination of road snow with polar organic chemicals has been studied, with a range beyond well-known pollutants such as metals and PAHs. A highly consistent pattern of traffic-related chemicals was found in road snow, without any clear dependence on traffic intensity, but they could be clearly distinguished from backyard snow samples used as reference. The traffic-related mixture was also supplemented with site-specific compounds, including pesticides, pharmaceuticals, and food additives. The oxidation product of 6-PPD associated with tire wear, namely 6-PPDQ, was present in all road snow samples. The observed concentrations indicated an acute toxicity risk for sensitive fish. Low removal rates were found for eight compounds (MCPA, tetracaine, N-ethyl-o-toluenesulfonamide, triethyl phosphate, denatonium, diphenhydramine, 2-methylthiobenzothiazole, and propiconazole). Therefore, among the compounds closely associated with snowmelt, especially N-ethyl-o-toluenesulfonamide, hardly remained in the WWTP. For other compounds, including 6-PPDQ, and other risk drivers, efficient removal processes may protect the aquatic environment from excessive toxicity.
The sampling campaign was conducted in the demonstration urban area in February 2021. A period of air temperature >0 °C was followed by a cold spell on February 6/7, during which snow accumulation heights of approximately 20 cm (. The cold period lasted until February 16, when temperatures rose to >0 °C and snowfall was followed by light rain. The rising temperatures resulted in the snow not being completely melted until February 19. Twenty snow samples were collected directly on both sides of roads with different traffic intensities in the distance between 8:00 and 12:00 on February 17, 2021. Snow deposits between 0.3 and 0.8 m from the road surface are called road snow. These samples contained visible brown-black particles and abrasives and were partially compacted and frozen. In addition, three snow samples were collected in urban areas without traffic as background references. At each location, approximately 3-5 L of snow were collected in stainless steel containers and transported to the laboratory within 4 h. All samples were subsequently stored at -20 °C, and batches of 5-6 samples were melted overnight and filtered using glass fiber filters, resulting in a final harvest of 1 L of water.

Custom Q&A

What is the molecular formula of N-Ethyl-o-toluenesulfonamide?

The molecular formula of N-Ethyl-o-toluenesulfonamide is C9H13NO2S.

What are the synonyms for N-Ethyl-o-toluenesulfonamide?

The synonyms for N-Ethyl-o-toluenesulfonamide include Benzenesulfonamide, N-ethyl-2-methyl-; N-Ethyltoluene-2-sulphonamide; and Ethyl tosylamide.

What is the CAS number for N-Ethyl-o-toluenesulfonamide?

The CAS number for N-Ethyl-o-toluenesulfonamide is 1077-56-1.

What is the boiling point of N-Ethyl-o-toluenesulfonamide?

The boiling point of N-Ethyl-o-toluenesulfonamide is 196°C.

What is the melting point of N-Ethyl-o-toluenesulfonamide?

The melting point of N-Ethyl-o-toluenesulfonamide is 344-350°C (lit.).

What is the flash point of N-Ethyl-o-toluenesulfonamide?

The flash point of N-Ethyl-o-toluenesulfonamide is 145.7°C.

What is the density of N-Ethyl-o-toluenesulfonamide?

The density of N-Ethyl-o-toluenesulfonamide is 1.153 g/cm³.

What is the physical state of N-Ethyl-o-toluenesulfonamide?

The physical state of N-Ethyl-o-toluenesulfonamide is solid.

What are some typical applications of N-Ethyl-o-toluenesulfonamide?

Some typical applications of N-Ethyl-o-toluenesulfonamide include its use as a dispersing agent, emulsifying agent, plasticizer, and lubricant.

What is the percentage of actives in N-Ethyl-o-toluenesulfonamide?

The percentage of actives in N-Ethyl-o-toluenesulfonamide is 95%.