649-15-0

Basic information

• Product Name: P-TOLUENESULFONYL-N,N-DIETHYLAMIDE
• Synonyms: n,n-diethyl-4-methyl-benzenesulfonamid;n,n-diethyl-p-toluenesulfonamid;P-TOLUENESULFONYL-N,N-DIETHYLAMIDE;N,N-DIETHYL-P-TOLUENESULFONAMIDE;Toluenesulfonyldiethylamide;p-Toluenesulfonyl-n-diethylamide;N,N-Dirthyl-P-toluenesulfonamide;N.N-Diethyl-p-toluenesulfonaMide(DETSA)
• CAS NO: 649-15-0
• Molecular Formula: C₁₁H₁₇NO₂S
• Molecular Weight: 227.32
• Mol File: 649-15-0.mol
• Article Data: 55

Chemical Properties

• Melting Point: 60 °C
• Boiling Point: 328.7 °C at 760 mmHg
• Flash Point: 152.6 °C
• Appearance: White/Crystalline
• Density: 1.112 g/cm³
• Storage Temp.: 2-8°C
• PKA: -4.69±0.70(Predicted)
• CAS DataBase Reference: P-TOLUENESULFONYL-N,N-DIETHYLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: P-TOLUENESULFONYL-N,N-DIETHYLAMIDE(649-15-0)
• EPA Substance Registry System: P-TOLUENESULFONYL-N,N-DIETHYLAMIDE(649-15-0)

Safety Data

• RTECS: XT5619800
• Hazardous Substances Data: 649-15-0(Hazardous Substances Data)

Usage

Uses

N,N-Diethyl-p-toluenesulfonamide is a useful reactant in organic synthesis.

Upstream product

• 74-96-4 ethyl bromide 
• 70-55-3 toluene-4-sulfonamide 
• 109-89-7 diethylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 80-39-7 N-ethyl-4-methyl-benzenesulfonamide 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 110-91-8 morpholine 
• 536-57-2 p-toluene sulfinic acid 
• 5775-33-7 N-chlorodiethylamine 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 155164-58-2 2-(4-methylbenzenesulfonyl)-4,5-dichloropyridazin-3-one 
• 20588-68-5 N,N-diethylsulfamoyl chloride 
• 108-88-3 toluene 
• 6873-59-2 N-(4-methylphenylsulfinyl)-N,N-diethylamine 

Downstream Products

• 59-26-7 N,N-diethylnicotinamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 349485-65-0 N,N-diethyl-4-methyl-2-(trimethylsilyl)benzenesulfonamide 
• 130824-05-4 4,4'-(1,2-ethanediyl)bis[N,N-diethylbenzenesulfonamide] 
• 224619-61-8 N,N-diethyl-2-iodo-4-methylbenzenesulfonamide 
• 25837-36-9 4,N,N-triethylbenzenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 1312206-60-2 N,N-diethyl-4-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide 
• 1338466-35-5 di-tert-butyl 2-(N,N-diethyl-4-methylbenzenesulfonamide)-hydrazine-1,2-dicarboxylate 
• 660-68-4 diethyl amine hydrochloride 
• 38938-22-6 diphenylthiophosphinic acid N,N-diethylamide 
• 1567898-20-7 1-(2-(N,N-diethylsulfamoyl)-5-methylbenzamido)cyclohexanecarboxylicacid 
• 1450829-61-4 diethyl (2-(N,N-diethylsulfamoyl)-5-methylphenyl)phosphonate 
• 142867-89-8 1,1'-μ-TosN(CH2CH2-)2-(2-Si(CH3)2C(CH3)3-1,2-C2B10H10)2 

Relevant articles and documents

Synthesis of Ferrocenesulfonyl Chloride: Key Intermediate toward Ferrocenesulfonamides

Ferrocenesulfonyl chloride is the key intermediate in the synthesis of ferrocenesulfonamides, a family of underexplored derivatives. A one-pot synthesis of this compound, able to easily deliver multigram quantities of product, is reported. An original protocol for the synthesis of ferrocenesulfonamides is described along with highlighting the reactivity difference between arene and ferrocenesulfonyl chlorides. Finally, an example of diastereoselective deprotolithiation of chiral ferrocenesulfonamides is described.

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.

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.