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105902

Sigma-Aldrich

p-Toluenesulfonamide

reagent grade, 97%

Synonym(s):

4-Methylbenzene-1-sulfonamide, p-Tosylamide

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About This Item

Linear Formula:
CH3C6H4SO2NH2
CAS Number:
70-55-3
Molecular Weight:
171.22
Beilstein/REAXYS Number:
472689
EC Number:
200-741-1
MDL number:
MFCD00011692
UNSPSC Code:
12352100
PubChem Substance ID:
24846713
NACRES:
NA.22

grade

reagent grade

assay

97%

form

solid

mp

134-137 °C (lit.)

solubility

DMSO: soluble

functional group

sulfonamide

SMILES string

Cc1ccc(cc1)S(N)(=O)=O

InChI

1S/C7H9NO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H2,8,9,10)

InChI key

LMYRWZFENFIFIT-UHFFFAOYSA-N

Gene Information

human ... CA1(759) , CA2(760) , CA5A(763) , CA5B(11238)

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General description

p-Toluenesulfonamide undergoes FeCl3-catalyzed direct substitution reaction with benzylic and allylic alcohols.It is employed as nucleophile in tetrabutylammonium fluoride (TBAF) catalyzed vinyl aziridine opening reaction.

Application

p-Toluenesulfonamide was used to prepare the precursor required for synthesis of ethyl 6-phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

395.6 °F - closed cup

flash_point_c

202 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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PHOSPHINE-CATALYZED [4+2] ANNULATION: SYNTHESIS OF ETHYL 6-PHENYL-1-TOSYL-1,2,5,6-TETRAHYDROPYRIDINE-3-CARBOXYLATE.
Kui Lu et al.
Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals, 2009(86), 212-224 (2010-02-18)
An efficient FeCl3 -catalyzed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or p-toluenesulfonamide.
Jana U, et al.
Tetrahedron Letters, 42(37), 6433-6435 (2001)
Charles H Reynolds et al.
Journal of medicinal chemistry, 51(8), 2432-2438 (2008-04-03)
Ligand efficiency (i.e., potency/size) has emerged as an important metric in drug discovery. In general, smaller, more efficient ligands are believed to have improved prospects for good drug properties (e.g., bioavailability). Our analysis of thousands of ligands across a variety
Yang Yang et al.
Organic letters, 13(20), 5608-5611 (2011-09-16)
BF(3)·OEt(2)-catalyzed direct cyanation of indoles and pyrroles using a less toxic, bench-stable, and easily handled electrophilic cyanating agent N-cyano-N-phenyl-para-toluenesulfonamide (NCTS) affords 3-cyanoindoles and 2-cyanopyrroles in good yields with excellent regioselectivity. The substrate scope is broad with respect to indoles and
Daniela Vullo et al.
Bioorganic & medicinal chemistry letters, 15(4), 971-976 (2005-02-03)
The inhibition of a newly cloned human carbonic anhydrase (CA, EC 4.2.1.1), isozyme VII (hCA VII), has been investigated with a series of aromatic and heterocyclic sulfonamides, including some of the clinically used derivatives (acetazolamide, methazolamide, ethoxzolamide, dichlorophenamide, dorzolamide, brinzolamide
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