918-05-8

Basic information

• Product Name: N,N-DIMETHYL METHANESULFONAMIDE
• Synonyms: TIMTEC-BB SBB007962;N,N-DIMETHYL METHANESULFONAMIDE;N,N-DIMETHYLMETHANESULPHONAMIDE;N,N-Dimethyl methanesulfonamide, 98+%
• CAS NO: 918-05-8
• Molecular Formula: C₃H₉NO₂S
• Molecular Weight: 123.17
• EINECS: 213-039-5
• Mol File: 918-05-8.mol

Chemical Properties

• Melting Point: 49 °C
• Boiling Point: 119-120°C 17mm
• Flash Point: 119-120°C/17mm
• Appearance: /
• Density: 1.158g/cm³
• Vapor Pressure: 1.84mmHg at 25°C
• Refractive Index: 1.45
• PKA: -3.35±0.70(Predicted)
• BRN: 1747409
• CAS DataBase Reference: N,N-DIMETHYL METHANESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIMETHYL METHANESULFONAMIDE(918-05-8)
• EPA Substance Registry System: N,N-DIMETHYL METHANESULFONAMIDE(918-05-8)

Safety Data

• Hazard Codes: T
• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• HazardClass: TOXIC
• Hazardous Substances Data: 918-05-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical and Pharmaceutical Industries:
N,N-Dimethyl methanesulfonamide is used as a solvent and reagent for its ability to dissolve a wide range of substances and facilitate various chemical reactions. Its strong solvating properties make it a valuable component in the synthesis of organic compounds.
Used in Organic Synthesis:
As a reaction medium, N,N-Dimethyl methanesulfonamide is used to carry out organic synthesis, providing a suitable environment for chemical reactions to occur efficiently.
Used in Drug Delivery Systems:
N,N-Dimethyl methanesulfonamide is utilized as a carrier in drug delivery systems, enhancing the transport and bioavailability of pharmaceutical agents.
Used in Materials Science:
N,N-DIMETHYL METHANESULFONAMIDE has been studied for its potential applications in materials science, where it may contribute to the development of new materials with unique properties.
Used in Electrolyte Additives for Lithium-Ion Batteries:
N,N-Dimethyl methanesulfonamide is being researched for use as an electrolyte additive in lithium-ion batteries, with the aim of improving their performance and stability.
Safety Precautions:
While N,N-Dimethyl methanesulfonamide offers numerous applications, it is essential to handle it with care due to its status as a skin and eye irritant. Ingestion or inhalation may also pose health risks, necessitating proper safety measures during its use.

InChI:InChI=1/C3H9NO2S/c1-4(2)7(3,5)6/h1-3H3

Upstream product

• 79687-63-1 (1,1-Dioxo-3-phenyl-1λ⁶-thietan-3-yl)-dimethyl-amine; hydrochloride 
• 506-59-2 N,N-dimethylammonium chloride 
• 124-63-0 methanesulfonyl chloride 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 124-40-3 dimethyl amine 
• 1184-85-6 N-methylmethane sulphonamide 
• 1774-47-6 trimethylsulfoxonium iodide 
• 3144-09-0 methanesulfonamide 
• 74-88-4 methyl iodide 
• 99337-23-2 C₃H₉NO₂S 
• 71999-99-0 (1,1-Dioxo-3-phenyl-1λ⁶-thietan-3-yl)-dimethyl-amine 
• 676-85-7 methylsulphinyl chloride 
• 16645-06-0 N,N-dimethylhydroxylamine hydrochloride 
• 51-80-9 bis-(dimethylamino)methane 

Downstream Products

• 2945-62-2 2-hydroxy-2,2-diphenyl-ethanesulfonic acid dimethylamide 
• 73281-91-1 N,N-dimethyl-2-oxo-2-phenylethane-1-sulfonamide 
• 14894-42-9 Phenylmethanesulfonic acid N,N-dimethylamide 
• 691004-40-7 (N,N-dimethylsulfamoylmethyl)(3-methylphenyl)ketone 
• 864301-08-6 C-[3-(2-Chloro-phenyl)-6-methylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-N,N-dimethyl-methanesulfonamide 
• 141-97-9 ethyl acetoacetate 
• 112497-63-9 N,N-dimethyl-2-oxopropane-1-sulfonamide 
• 63517-92-0 2-(1-Hydroxy-cyclohexyl)-ethanesulfonic acid dimethylamide 
• 1402844-84-1 N-methyl-N-((2-phenyl-1H-imidazol-1-yl)methyl)methanesulfonamide 
• 1245623-13-5 tert-butyl {2-(dimethylsulphamoyl)-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate 
• 1094164-92-7 N-benzyloxy-2-dimethylsulfamoyl-N-methyl acetamide 

Relevant articles and documents

A straightforward synthesis of 5-sulfonamidomethyl substituted 4,7-dihydroazolo[1,5-a]pyrimidines

4,7-Dihydroazolo[1,5-a]pyrimidin-5-ylmethanesulfonamides are side-products of the three-component Biginelli-like reaction of aminoazoles, aldehydes and N,N-dialkyl-2-ketomethanesulfonamides. Herein, we report a straightforward synthesis of 5-sulfonamidomethyl substituted 4,7-dihydroazolo[1,5-a]pyrimidines by a two-component condensation of aminoazoles and N,N-dialkyl(cinnamoyl)methanesulfonamides in DMF at reflux. The starting N,N-dialkyl-2-ketomethanesulfonamides can be obtained by either lithiation of N,N-dialkylmethanesulfonamides and reaction with aldehydes followed by oxidation of the resulting alcohols or by Claisen condensation of N,N-dialkylmethanesulfonamides with the corresponding esters. The chemical structures of all synthesized compounds are supported by 1H and 13C NMR-spectroscopy, mass spectrometry and elemental analysis.

Aryldiazonium bis(trifluoromethyl)imides

Aryldiazonium bis(trifluoromethyl)imides, [ArN2][N(CF 3)2], are the first examples of diazonium salts with this type of anion. Their syntheses and properties will be presented and compared to aryldiazonium bis(trifluoromethylsulfonyl)imides. [ArN2][N(CF 3)2] are less stable diazonium salts in comparison to [ArN2][N(SO2CF3)2] due to the higher nucleophilicity of the [N(CF3)2]- anion.

Microwave-assisted efficient methylation of alkyl and arenesulfonamides with trimethylsulfoxonium iodide and KOH

A solvent-free synthesis of N-methyl and N,N-dimethylsulfonamides has been achieved by treating the primary and secondary sulfonamides with Me3S+OI- and KOH under microwave irradiation on alumina support. Copyright Taylor & Francis Group, LLC.

Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors

4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Muenchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and C log P values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development.

A useful Pd-catalyzed Negishi coupling approach to benzylic sulfonamide derivatives

(Chemical Equation Presented) A mild catalytic system to access diversely functionalized benzylic sulfonamides has been developed. Palladium-catalyzed α-arylation by Negishi cross-coupling of sulfonamide-stabilized anions and a wide range of aryl iodides, bromides, and triflates constitutes a practical strategy for the synthesis of various benzylic sulfonamides.

Multinuclear NMR Study of Variously Substituted Sulphonamides and Sulphinamides

13C, 15N and 17O NMR chemical shifts, and also 1J(CH) and 1J(NH) values, have been determined for variously substituted sulphonamides and some sulphinamides, either neat or in acetone or dimethyl sulphoxide solution.The effect of benzene ring substitutens on the chemical shifts of nitrogen and oxygen nuclei is slight, but N-substitution changes the shielding of both nuclei.Generally, an N-methyl substituent shields an amide nitrogen and an N,Ndimethyl substituent gives further slight shielding.On the other hand, an N-phenyl substituent deshilds the nitrogen strongly, but the deshielding effect of an N,N-diphenyl substituent is markedly smaller.The sulphonyl oxygens are deshilded relative to the sulphinyl oxygens, and N-methyl and N,N-dimethyl substituents shild the oxygen nucleus.The effect of N-phenyl and N,N-diphenyl substituents on the shielding of the oxygen atoms of the sulphonyl group is slight.The direct 1J(CH) coupling constants are similar, but they are characteristic of different type of sulphur amides.The 1J(NH) values are of the same order of magnitude for sulphonamides and sulphinamides, but are clearly smaller for N-unsubstituted amides than for N-substituted compounds.KEY WORDS Sulphonamide Sulphinamide Multinuclear NMR

Reaction between N,N-Dialkylhydroxylamines and Sulphinyl Chlorides

The reactions of several N,N-dialkylhydroxylamines with methane- and benzene-sulphinyl chlorides below 0 deg C give O-sulphinylated intermediates.These rearrange at ambient temperatures to give the corresponding sulphonamides and in some cases the imines and products derived from the decomposition of the accompanying sulphinic acids.N.m.r. spectra ((1H and 13C) show strong polarizations in the sulphonamides, indicating a radical-cage mechanism.No CIDNP signals were observed in the imines, which can be formed in a six-electron symmetry-allowed cyclic elimination.

The Reaction between N,N-Dialkylhydroxylamines and Sulphinyl Chlorides

The reaction of N,N-dialkylhydroxylamines with sulphinyl chlorides proceeds via an O-sulphinylated hydroxylamine intermediate, which has been isolated and characterised by n.m.r. spectroscopy; rearrangement of this intermediate to the sulphonamide has been shown to involve an aminyl radical.

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.

α,N-Alkanesulfonamide Dianions: Formation and Chemoselective C-Alkylation

Mono-N-substituted alkanesulfonamides such as 11 (Scheme I) can be treated with 2 equiv of a strong base (n-butyllithium or LDA) to generate the hitherto unreported dianionic species 12.Addition of electrophiles (alkylhalides, aldehydes, ketones, nitriles) to THF solutions of these dianions results in clean, chemoselective reaction on the carbon atom.Removal of the "protecting" group from nitrogen releases a primary sulfonamide, which may then be selectively functionalized.This method permits the preparation of a wide variety of substituted sulfonamides that might otherwise prove difficult to synthesize.As demonstration of the further utility of these adducts, β-hydroxy sulfonamides such as 14 were converted to either β-styrenesulfonamides 15 (and 16) or 1,2-thiazetidine 1,1-dioxides (18) (Scheme II).