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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
Improvement of the synthesis of diphenylmethyl 7beta-(o-hydroxy)benzylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate.
2001 Aug
Samarium(0) and 1,1'-dioctyl-4,4'-bipyridinium dibromide: a novel electron-transfer system for the chemoselective reduction of aromatic nitro groups.
2001 Feb 9
Dichloro[N-[3-(eta5-cyclopentadienyl)propyl]-4-toluenesulfonamido-kappa2N,O]titanium(IV).
2002 Nov
Alkynyliodonium salts in organic synthesis. Application to the total synthesis of the tropoloisoquinoline alkaloid pareitropone.
2002 Oct 2
1,2-Silyl-migrative cyclization of vinylsilanes bearing an amino group.
2003 Jan
Employment of palladium pincer-complexes in phenylselenylation of organohalides.
2005 Nov 11
Lewis base catalyzed Mannich-type reactions between trimethylsilyl enol ethers and aldimines.
2006 Jun 23
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Human pharmaceuticals, antioxidants, and plasticizers in wastewater treatment plant and water reclamation plant effluents.
2007 Feb
Quantitative determination of three sulfonamides in environmental water samples using liquid chromatography coupled to electrospray tandem mass spectrometry.
2007 Jul 20
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
Gemcitabine plus cisplatin chemotherapy with concurrent para-toluenesulfonamide local injection therapy for peripherally advanced nonsmall cell lung cancer larger than 3 cm in the greatest dimension.
2009 Oct
Copper-catalyzed cascade syntheses of 2H-benzo[b][1,4]thiazin-3(4H)-ones and quinoxalin-2(1H)-ones through capturing S and N atom respectively from AcSH and TsNH(2).
2010 Aug 20
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
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