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Details

Stereochemistry ACHIRAL
Molecular Formula C7H9NO2S
Molecular Weight 171.217
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of P-TOLUENESULFONAMIDE

SMILES

CC1=CC=C(C=C1)S(N)(=O)=O

InChI

InChIKey=LMYRWZFENFIFIT-UHFFFAOYSA-N
InChI=1S/C7H9NO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H2,8,9,10)

HIDE SMILES / InChI

Molecular Formula C7H9NO2S
Molecular Weight 171.217
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

p-Toluene sulfonamide was used to prepare the precursor required for synthesis of ethyl 6-phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate. It acts as a derivative of ammonia activated to alkylation by alkyl halides is exemplified by the synthesis of N-tosyl-2,3-dihydroisoindole from o-xylylene dibromide. It is a precursor of N-tosyl imines. Hybrid compounds of tacrine and p-toluenesulfonamide are effective inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with the preferential inhibition of BChE. p-Toluenesulfonamide has been employed as nucleophile during tetrabutylammonium fluoride (TBAF) catalyzed vinyl aziridine opening reaction and as a reagent during selective aziridination of olefins catalyzed by dirhodium (II) caprolactamate.

Approval Year

PubMed

PubMed

TitleDatePubMed
Bis(mu-N-[2-(eta[5]-cyclopentadienyl)-ethyl]-4-toluenesulfonamido-N,O:O')-bis[bis(trifluoromethanesulfonato-O)-titanium(II)]bis(dichloromethane) solvate.
2001 Apr
Design and synthesis of a series of indole glycoprotein IIb/IIIa inhibitors.
2002 Jan
Dichloro[N-[3-(eta5-cyclopentadienyl)propyl]-4-toluenesulfonamido-kappa2N,O]titanium(IV).
2002 Nov
Transition metal-catalyzed regio- and stereoselective aminobromination of olefins with TsNH2 and NBS as nitrogen and bromine sources.
2003 Mar 20
Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate.
2005 Jun 23
Platinum-based catalysts for the hydroamination of olefins with sulfonamides and weakly basic anilines.
2005 Sep 14
Mitochondrial permeability transition induced by novel pyridothiopyranopyrimidine derivatives: potential new antimitochondrial antitumour agents.
2006 Dec 15
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Photochromism, anomalous multi-banded fluorescence and laser properties of some amino- and tosyl-amino derivatives of oxadiazole.
2006 Sep
Hydroamination and hydroalkoxylation catalyzed by triflic acid. Parallels to reactions initiated with metal triflates.
2006 Sep 14
Tandem epoxide or aziridine ring opening by azide/copper catalyzed [3+2] cycloaddition: efficient synthesis of 1,2,3-triazolo beta-hydroxy or beta-tosylamino functionality motif.
2007 Dec 7
Quantitative determination of three sulfonamides in environmental water samples using liquid chromatography coupled to electrospray tandem mass spectrometry.
2007 Jul 20
Behaviour and biodegradation of sulfonamides (p-TSA, o-TSA, BSA) during drinking water treatment.
2008 Apr
Use of chemometric methodology in optimizing conditions for competitive binding partial filling affinity capillary electrophoresis.
2008 Aug
[Dose-effect relationship of para-toluenesulfonamide for treatment of hepatocellular carcinoma in rats].
2008 Feb
2,2-Dichloro-N-(4-methyl-phenyl-sulfonyl)acetamide.
2008 Jul 16
Frequency and main sites of allergic contact dermatitis caused by nail varnish.
2008 Nov-Dec
Sensitivity of nuclear-quadrupole double-resonance detection of half-integer spin nuclei.
2008 Oct
RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage: their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines.
2008 Oct 1
Intramolecular anodic olefin coupling reactions: the use of a nitrogen trapping group.
2008 Oct 15
2-Chloro-benzene-sulfonamide.
2009 Aug 15
o-Toluene-sulfonamide: a redetermination.
2009 Aug 29
Copper powder-catalyzed regio- and stereoselective aminobromination of alpha,beta-unsaturated ketones with TsNH2 and NBS as nitrogen and halogen sources.
2009 Feb 6
Addition reactions of chloro- or iodomethyllithium to imines. Synthesis of enantiopure aziridines and beta-chloroamines.
2009 Mar 20
2-[(N-Benzyl-4-methyl-benzene-sul-fon-amido)meth-yl]pyridinium nitrate.
2009 Oct 23
N-(4-Chloro-benzo-yl)-4-methyl-benzene-sulfonamide.
2010 Jan 9
Intramolecular anodic olefin coupling reactions and the synthesis of cyclic amines.
2010 Mar 3
N-(4-Chloro-pyridin-2-yl)-N-meth-oxy-methyl-4-methyl-benzene-sulfonamide.
2010 Nov 27
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:41:33 GMT 2023
Edited
by admin
on Fri Dec 15 15:41:33 GMT 2023
Record UNII
I8266RI90M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
P-TOLUENESULFONAMIDE
HSDB   USP-RS  
Common Name English
4-TOLUENESULFONAMIDE
Systematic Name English
GLICLAZIDE IMPURITY A [EP IMPURITY]
Common Name English
P-TOLUENESULFONAMIDE [HSDB]
Common Name English
P-TOLUENESULFONAMIDE [USP-RS]
Common Name English
P-TOSYLAMIDE
Common Name English
4-METHYLBENZENESULFONAMIDE
Systematic Name English
P-TOLUENESULFONYLAMIDE
Common Name English
P-METHYLBENZENESULFONAMIDE
Common Name English
BENZENESULFONAMIDE, 4-METHYL-
Systematic Name English
TOLUENESULFONAMIDE, P-
Common Name English
PARA-TOLUENESULFONAMIDE
Common Name English
TOLUENE-4-SULPHONAMIDE
Systematic Name English
NSC-9908
Code English
TOLBUTAMIDE IMPURITY A [EP IMPURITY]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 553516
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
Code System Code Type Description
FDA UNII
I8266RI90M
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
PRIMARY
CAS
70-55-3
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID8029105
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
PRIMARY
CHEBI
34435
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
PRIMARY
HSDB
5203
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
PRIMARY
RS_ITEM_NUM
1672020
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
PRIMARY
PUBCHEM
6269
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-741-1
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
PRIMARY
MESH
C025417
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
PRIMARY
NSC
9908
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
PRIMARY
NCI_THESAURUS
C156702
Created by admin on Fri Dec 15 15:41:33 GMT 2023 , Edited by admin on Fri Dec 15 15:41:33 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
MAJOR
URINE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY