3768-63-6

Basic information

• Product Name: N,N,N',N'-TETRAMETHYLSULFONAMIDE
• Synonyms: TIMTEC-BB SBB007951;RARECHEM AM UC 0110;NNN'N'-TETRAMETHYLSULFAMIDE;N,N,N',N'-TETRAMETHYLSULFONAMIDE;N,N,N',N'-TETRAMETHYLSULPHONAMIDE;N,N,N’,N’-Tetramethylsulfuricdiamide;Sulfamide, tetramethyl-;sulfamide,tetramethyl-
• CAS NO: 3768-63-6
• Molecular Formula: C₄H₁₂N₂O₂S
• Molecular Weight: 152.22
• Mol File: 3768-63-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 70-73°C
• Boiling Point: 225°C
• Flash Point: 81.2°C
• Appearance: /solid
• Density: 1.124 (estimate)
• Refractive Index: 1.6430 (estimate)
• PKA: -4.33±0.70(Predicted)
• BRN: 1759783
• CAS DataBase Reference: N,N,N',N'-TETRAMETHYLSULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N',N'-TETRAMETHYLSULFONAMIDE(3768-63-6)
• EPA Substance Registry System: N,N,N',N'-TETRAMETHYLSULFONAMIDE(3768-63-6)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 3768-63-6(Hazardous Substances Data)

Usage

General Description

N,N,N',N'-Tetramethylsulfonamide is a chemical compound with the molecular formula C4H12N2O2S. It is a highly polar and aprotic solvent that is commonly used in organic synthesis and as a reagent in chemical reactions. It has a wide range of applications, including as a solvent in the production of pharmaceuticals, as a reaction solvent in chemical processes, and as a solvent in lithium-ion batteries. It is also used as a reagent in the synthesis of various organic compounds and as a stabilizer in the production of polymers. Additionally, N,N,N',N'-Tetramethylsulfonamide is considered to be a safer alternative to dimethyl sulfoxide (DMSO) due to its lower toxicity and milder odor.

Upstream product

• 67-66-3 chloroform 
• 124-40-3 dimethyl amine 
• 13360-57-1 dimethylamino sulfonyl chloride 
• 246851-80-9 1-(2-amino-phenyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester 
• 57-14-7 N,N-Dimethylhydrazine 
• 29777-18-2 C₅H₁₅N₂O₂S⁽¹⁺⁾*Cl^(1-) 

Downstream Products

• 506-59-2 N,N-dimethylammonium chloride 
• 13113-78-5 (dimethylamino)di-n-propylborane 
• 13360-57-1 dimethylamino sulfonyl chloride 

Relevant articles and documents

METHOD FOR MAKING N-(FLUOROSULFONYL) DIMETHYLAMINE

Dimethylamine (Me2NH) is reacted with sulfuryl fluoride (SO2F2) to form at least a first phase comprising N-(fluoro sulfonyl) dimethylamine (FSO2NMe2), tetramethylsulfamide (SO2(NMe2)2), or a combination thereof. A second phase, which may include dimethylamine hydrofluoride (Me2NH2F), may be also formed and separated from the first phase. FSO2NMe2 or SO2(NMe2)2 is then isolated from the first phase. For example, the first phase may be a liquid phase, and FSO2NMe2 and SO2(NMe2)2 are separated by distillation, optionally under reduced pressure.

Betylates. 1. Synthesis and reactions of an isolable betylate, N,N-dimethyl-N-(phenoxysulfonyl)methanaminium fluorosulfate

Phenyl betylate fluorosulfate (2), the first example of a "betylate" (trialkylammoniosulfate ester), has been prepared by methylation of phenyl N,N-dimethylsulfamate with methyl fluorosulfate.Nucleophiles react with 2 either by attack on the sulfur or methyl carbon atoms, but with no sign of any products derived from benzyne or the phenyl cation.A synthesis of enol N,N-dimethylsulfamates has been devised using a reagent, Me2NSO2N(1+)Me3 FSO3(1-), prepared from tetramethylsulfamide and methyl fluorosulfate, but no satisfactory method was found for converting the sulfamic ester to the betylate.Evidence is presented that phenyl chlorosulfate reacts with trimethylamine to give the phenylbetylate which then undergoes further reaction.