10285-91-3

Basic information

• Product Name: N-Butyl-N,4-dimethylbenzenesulfonamide
• Synonyms: N-Butyl-N,4-dimethylbenzenesulfonamide
• CAS NO: 10285-91-3
• Molecular Formula: C₁₂H₁₉NO₂S
• Molecular Weight: 241.35
• Mol File: 10285-91-3.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Butyl-N,4-dimethylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Butyl-N,4-dimethylbenzenesulfonamide(10285-91-3)
• EPA Substance Registry System: N-Butyl-N,4-dimethylbenzenesulfonamide(10285-91-3)

Safety Data

• Hazardous Substances Data: 10285-91-3(Hazardous Substances Data)

Upstream product

• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 71-36-3 butan-1-ol 
• 142-96-1 dibutyl ether 
• 98-59-9 p-toluenesulfonyl chloride 
• 927-62-8 N,N-dimethylbutylamine 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 110-68-9 N-n-butyl-N-methylamine 

Relevant articles and documents

1,1′-(azodicarbonyl)dipiperidine-tributylphosphine, a new reagent system for mitsunobu reaction

The 1,1′-(azodicarbonyl)dipiperidine (ADDP)-tributylphosphine (TBP) system was developed as a new institute of the Mitsunobu reagent. The new system activates nitrogen or carbon nucleophiles, known to be innert or poorly reactive with the Mitsunobu reagent, to react with alcohols satisfactorily forming C-N or C-C bonds. The inversion of stereogenic carbinyl carbons was confirmed in the acylaltion reaction of two sec-alcohols.

The mechanism of alkene elimination from protonated toluenesulphonamides generated by electrospray ionisation

The positive ion electrospray mass spectra of a range of sulphonamides of general structure CH3C6H4SO2NHR1 [R1 = CnH2n+1 (n = 1-7), CnH2n-1 (n = 3, 4), C6H5, C6H5CH2 and C6H5CH(CH3)] and CH3C6H4SO2NR1R2 [R1, R2 = CnH2n+1 (n = 1-8)] are reported and discussed. The protonated sulphonamides derived from saturated primary and secondary aliphatic amines generally fragment to only a limited extent unless energised by collision. Two general fragmentations are observed: firstly, elimination of an alkene, CnH2n, obtained by hydrogen abstraction from one of the CnH2n+1 alkyl groups on nitrogen; secondly, cleavage to form CH3C6H4SO2+. The mechanism by which an alkene is lost has been probed by studying the variation of the intensity of the [M + H - CnH2n]+ signal with the structure of the alkyl substituent(s) on nitrogen and by monitoring the competition between the loss of different alkenes from protonated unsymmetrical sulphonamides in which two different alkyl groups are attached to nitrogen. This fragmentation is favoured by branching of the alkyl group at the carbon atom directly attached to nitrogen, thus suggesting that it involves a mechanism in which the stability of the cation obtained by stretching the bond connecting the nitrogen atom to the alkyl group is critical. This interpretation also explains the competition between alkene elimination and cleavage to form CH3C6H4SO2+ (and, in some cases, cleavage to form C6H5CH2+ or [C6H5CHCH3]+).

TiCl4-mediated direct N-alkylation of sulfonamides with inactive ethers

A TiCl4-mediated intermolecular or intramolecular direct N-alkylation reaction of sulfonamides with inactive ethers as alkylating agents was successfully achieved. This method provides a novel approach towards N-alkyl sulfonamides from inactive ethers via an easy workup procedure. Georg Thieme Verlag Stuttgart · New York.

N,N,N',N'-Tetramethylazodicarboxamide (TMAD), A New Versatile Reagent for Mitsunobu Reaction. Its Application to Synthesis of Secondary Amines

N,N,N',N'-Tetramethylazodicarboxamide, (TMAD), was found to be more versatile in the Mitsunobu reaction than traditional diethyl azodicarboxylate or recently developed 1,1'-(azodicarbonyl)dipiperidine, when used in combination with tributylphosphine in benzene.The usefulness of the reagent was demonstrated by the highly efficient two-step synthesis of benzylcrotylamine from N-benzyltrifluoroacetamide.