14417-01-7

Basic information

• Product Name: N,N-DIMETHYLBENZENESULPHONAMIDE
• Synonyms: N,N-DIMETHYLBENZENESULPHONAMIDE
• CAS NO: 14417-01-7
• Molecular Formula: C₈H₁₁NO₂S
• Molecular Weight: 185.24
• Mol File: 14417-01-7.mol

Chemical Properties

• Melting Point: 45.5-46.5 °C
• Boiling Point: 283.9°Cat760mmHg
• Flash Point: 125.5°C
• Appearance: /
• Density: 1.195g/cm³
• Vapor Pressure: 0.00308mmHg at 25°C
• Refractive Index: 1.541
• PKA: -4.73±0.70(Predicted)
• CAS DataBase Reference: N,N-DIMETHYLBENZENESULPHONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYLBENZENESULPHONAMIDE(14417-01-7)
• EPA Substance Registry System: N,N-DIMETHYLBENZENESULPHONAMIDE(14417-01-7)

Safety Data

• Hazardous Substances Data: 14417-01-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,N-DIMETHYLBENZENESULPHONAMIDE is used as an intermediate for the synthesis of phenylsulfonamides, which possess anticonvulsant properties. These phenylsulfonamides are particularly useful in the treatment of epilepsy, as they help to control seizures and manage the symptoms associated with the condition.
The compound's role in the pharmaceutical industry is significant, as it contributes to the development of medications that can improve the quality of life for individuals suffering from epilepsy. By acting as a key intermediate in the synthesis of anticonvulsant drugs, N,N-DIMETHYLBENZENESULPHONAMIDE enables the creation of more effective treatments for this neurological disorder.

InChI:InChI=1/C8H11NO2S/c1-9(2)12(10,11)8-6-4-3-5-7-8/h3-7H,1-2H3

Upstream product

• 124-40-3 dimethyl amine 
• 98-09-9 benzenesulfonyl chloride 
• 98-10-2 benzenesulfonamide 
• 74-88-4 methyl iodide 
• 2083-91-2 N,N-Dimethyltrimethylsilylamine 
• 85939-88-4 5-(dimethylamino)-1-thiacyclooctane 
• 7732-18-5 water 
• 60-29-7 diethyl ether 
• 4972-29-6 benzenesulphinyl chloride 
• 108-98-5 thiophenol 
• 68-12-2 N,N-dimethyl-formamide 
• 7463-22-1 N,N-Dimethyl-p-chlorobenzenesulfonamide 
• 22184-85-6 N,N-dimethyl-p-iodobenzenesulfonamide 
• 707-60-8 4-bromo-N,N-dimethylbenzenesulfonamide 

Downstream Products

• 124-40-3 dimethyl amine 
• 98-09-9 benzenesulfonyl chloride 
• 123-56-8 Succinimide 
• 72802-68-7 N-methyl-N-succinimidomethylbenzenesulphonamide 
• 486422-05-3 N,N-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide 
• 152352-10-8 1-(9,10-Dihydro-9,10-methanoanthracen-9-ylmethyl)-4-(2-N,N-dimethylsulfamoylphenyl)piperidin-4-ol 
• 4058-04-2 N-phenyl-2,6-dimethylaniline 
• 1450829-80-7 diethyl (2-(N,N-dimethylsulfamoyl)phenyl)phosphonate 
• 179676-03-0 (C₆H₄(SO₂N(CH₃)2))HgCl 
• 105332-22-7 C₆H₅SO₂N(CH₃)2(AlBr₃)2 
• 105332-19-2 C₆H₅SO₂N(CH₃)2(AlBr₃) 
• 151868-16-5 N,N-DIMETHYL-2-FLUOROBENZENESULFONAMIDE 
• 178432-25-2 (2-(N,N-dimethylsulfamoyl)phenyl)boronic acid 
• 4917-54-8 N-formyl benzenesulfonamide 

Relevant articles and documents

Benzenesulfonyl chloride with primary and secondary amines in aqueous media - Unexpected high conversions to sulfonamides at high pH

We have determined pH-yield profiles under pseudo-first-order conditions of the reactions of benzenesulfonyl chloride with a set of primary and secondary water-soluble alkylamines, and have found with certain amines, such as dibutylamine, a profile taking the form of a sigmoid pH-yield curve with relatively high yields of the sulfonamide persisting with increasing basicity up to and including 1.0 mol/L sodium hydroxide. This behaviour is quantitatively accounted for by invoking, in addition to the usual second-order reaction of the sulfonyl chloride with the amine, two third-order terms (i) one first-order in sulfonyl chloride, amine and hydroxide anion, and (H) another first-order in sulfonyl chloride and second-order in the amine. The importance of the third-order terms correlates approximately with the total number of alkyl carbon atoms in the amine, and this in turn is regarded as related to the hydrophobic character of the amine. Experiments to test this picture included: (i) observation of a bell-shaped curve with bis(2-methoxyethyl)amine, (H) in the reaction of dibutylamine in THF-H2O (1:1), and also (iii) in the reaction of dibutylamine in 1.0 mol/L tetrabutylammonium bromide, and (iv) increase in the contributions of the third-order terms in 1.0 mol/L aqueous sodium chloride. Preparative reactions with dibutylamine, 1-octylamine, and hexamethylenimine in 1.0 mol/L aqueous sodium hydroxide with a 5% excess of benzenesulfonyl chloride gave, respectively, 94%, 98%, and 97% yields of the corresponding sulfonamides.

Carbon-13, Nitrogen-15, Oxygen-17 and Sulphur-33 NMR Chemical Shifts of Some Sulphur Amides and Related Compounds

15N, 17O and 33S NMR chemical shifts were determined for some aliphatic and aromatic sulphonamides, sulphinamides, sulphenamides and related sulphones and sulphoxides.The 17O and 33S NMR chemical shifts change only slightly for the sulphonyl compounds.In the sulphinyl compounds, on the other hand, the presence of nitrogen causes a noticeable shift to higher frequencies in the 17O resonance.The differences between the 17O chemical shifts of sulphinyl and sulphonyl compounds are more noticeable than those between sulphinamides and sulphoxides.The 15N NMR chemical shifts of sulphon-, sulphin- and sulphenamides reflectbwell the effect of the environments of both nitrogen and the adjacent sulphur atom.The correlations between 15N, 17O and 33S NMR chemical shifts and the structures of sulphur amides and related sulphones and sulphoxides are discussed.The chemical shifts of the 13C nuclei are also presented.

Aryl-aryl coupling via directed lithiation and oxidation

Aryl lithium reagents formed by directed lithiation reactions undergo transmetallation with copper(I) salts to form organocuprates, which may be efficiently oxidized to yield ortho-substituted biaryls. The Royal Society of Chemistry 2005.

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

Debenzylative Sulfonylation of Tertiary Benzylamines Promoted by Visible Light

An efficient, general, inexpensive, and environmentally friendly photosynthesis of sulfonamides via visible light promoted debenzylative sulfonylation of tertiary benzylamines is described. Compared to the traditional S?N coupling reactions, which are promoted by oxidative C?N bond cleavage of symmetrical tertiary alkylamines, this strategy provides a selective C?N bond cleavage protocol and avoids the use of transition-metal, explosive oxidants, and ligands.

Controlled synthesis of N, N-dimethylarylsulfonamide derivatives as nematicidal agents

Gramine can be intelligently and efficiently supplied with N, N-dimethylamino group and then reacted with the corresponding sulfonyl chlorides to synthesize N, N-dimethylarylsulfonamides. We herein designed and controlled synthesis of N, N-dimethylarylsulfonamide derivatives, and first reported the results of the nematicidal activity of 15 title compounds 3a-o against Meloidogyne incongnita in vitro, respectively. Among all of the title derivatives, compounds 3a, 3c, 3k, and 3o exhibited potent nematicidal activity with median lethal concentration (LC50) values ranging from 0.22 to 0.26 mg/L. Most noteworthy, N, N-dimethyl-4-methoxyphenylsulfonamide (3c) and N, N-dimethyl-8-quinolinesulfonamide (3o) showed the best promising and pronounced nematicidal activity, with LC50 values of 0.2381 and 0.2259 mg/L, respectively.

Preparation method of N,N-dimethylsulfamide derivatives

The invention discloses a preparation method of N,N-dimethylsulfamide derivatives and belongs to the technical field of synthesis of medical compounds. The preparation method comprises the following steps: reacting gramine, a reactant with sulfonyl chloride groups and an alkaline substance with any one of solvents such as CH2Cl2, CH3COCH3 and CH3CN at a temperature of minus 15 DEG C to 80 DEG C for 24-48 hours so as to obtain the product, wherein the molar ratio of the gramine to the reactant to the alkaline substance is (1.0-2.0):(1.2-4.0):(1.5-6.0). The N,N-dimethylsulfamide derivatives can be simply and efficiently prepared withlow cost, and the yield is up to 70-98%.

Charge-Transfer Complex Promoted Regiospecific C?N Bond Cleavage of Vicinal Tertiary Diamines

A catalyst-free, charge-transfer complex promoted coupling of sulfonyl chlorides with vicinal tertiary diamines to generate sulfonamides is presented. Mechanistic studies showed that these reactions are proceeded via charge transfer of vicinal tertiary diamines to sulfonyl chlorides, forming the unstable sulfonyl quaternary ammonium like complexes which induced the regiospecific intramolecular C?N bond cleavage of vicinal tertiary diamines. (Figure presented.).

Potassium tert-butoxide-mediated metal-free synthesis of sulfonamides from sodium sulfinates and N,N-disubstituted formamides

By using formamides as amine sources, a novel and efficient KO-t-Bu mediated amination of sodium sulfinates has been developed. The reaction utilizes readily available starting materials under metal-free conditions, thus providing an alternative and attractive route to sulfonamides.