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236330

Sigma-Aldrich

p-Toluenesulfonamide

ReagentPlus®, ≥99%

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:
24854164
NACRES:
NA.22

product line

ReagentPlus®

assay

≥99%

form

solid

mp

134-137 °C (lit.)

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

Cyanomethylenetributylphosphorane (CMBP)-mediated reaction of p-toluenesulfonamide with alcohols has been investigated.

Application

p-Toluenesulfonamide has been employed:
  • as nucleophile during tetrabutylammonium fluoride (TBAF) catalyzed vinyl aziridine opening reaction
  • as reagent during selective aziridination of olefins catalyzed by dirhodium (II) caprolactamate

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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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Arthur J Catino et al.
Organic letters, 7(13), 2787-2790 (2005-06-17)
[reaction: see text] A mild, efficient, and selective aziridination of olefins catalyzed by dirhodium(II) caprolactamate [Rh(2)(cap)(4).2CH(3)CN] is described. Use of p-toluenesulfonamide (TsNH(2)), N-bromosuccinimide (NBS), and potassium carbonate readily affords aziridines in isolated yields of up to 95% under extremely mild
E Simone et al.
Lab on a chip, 18(15), 2235-2245 (2018-06-28)
In this work, a novel multi-microfluidic crystallization platform called MMicroCryGen is presented, offering a facile methodology for generating individual crystals for fast and easy screening of the polymorphism and crystal habit of solid compounds. The MMicroCryGen device is capable of
Mitsunobu-type alkylation of p-toluenesulfonamide. A convenient new route to primary and secondary amines.
Tsunoda T, et al.
Tetrahedron Letters, 37(!4), 2457-2458 (1996)
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
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