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
• Article Data: 33

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

N,N-Dimethylbenzenesulfonamide is an intermediate used in the preparation of phenylsulfonamides with anticonvulsant properties for epilepsy treatment.

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

Upstream product

• 60-29-7 diethyl ether 
• 98-09-9 benzenesulfonyl chloride 
• 75-50-3 trimethylamine 
• 98-10-2 benzenesulfonamide 
• 74-88-4 methyl iodide 
• 122-39-4 diphenylamine 
• 515-46-8 Ethyl benzenesulfonate 
• 19620-78-1 O,O-diphenyl N-dimethylamidophosphite 
• 124-40-3 dimethyl amine 
• 98-59-9 p-toluenesulfonyl chloride 
• 6840-01-3 (dimethylamino)(diphenyl)phosphine 
• 80-18-2 Methyl benzenesulfonate 
• 7732-18-5 water 
• 5183-78-8 methyl(phenylsulfonyl)amide 

Downstream Products

• 611-74-5 N,N-dimethylbenzamide 
• 124-40-3 dimethyl amine 
• 98-09-9 benzenesulfonyl chloride 
• 151868-16-5 N,N-DIMETHYL-2-FLUOROBENZENESULFONAMIDE 
• 1450829-80-7 diethyl (2-(N,N-dimethylsulfamoyl)phenyl)phosphonate 
• 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 
• 179676-03-0 (C₆H₄(SO₂N(CH₃)2))HgCl 
• 105332-22-7 C₆H₅SO₂N(CH₃)2(AlBr₃)2 
• 105332-19-2 C₆H₅SO₂N(CH₃)2(AlBr₃) 
• 178432-25-2 (2-(N,N-dimethylsulfamoyl)phenyl)boronic acid 
• 4917-54-8 N-formyl benzenesulfonamide 
• 98-10-2 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.

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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.

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.

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%.