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132004

Sigma-Aldrich

p-Toluenesulfonyl hydrazide

97%

Synonym(s):

p-Toluenesulfonhydrazide, p-Toluenesulfonic acid hydrazide, p-Toluenesulfonyl hydrazide, Tosylhydrazide

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About This Item

Linear Formula:
CH3C6H4SO2NHNH2
CAS Number:
1576-35-8
Molecular Weight:
186.23
Beilstein:
610130
EC Number:
216-407-3
MDL number:
MFCD00007588
UNSPSC Code:
12352100
PubChem Substance ID:
24847540
NACRES:
NA.22

Assay

97%

form

powder

mp

103-108 °C (lit.)

SMILES string

Cc1ccc(cc1)S(=O)(=O)NN

InChI

1S/C7H10N2O2S/c1-6-2-4-7(5-3-6)12(10,11)9-8/h2-5,9H,8H2,1H3

InChI key

ICGLPKIVTVWCFT-UHFFFAOYSA-N

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Application

p-Toluenesulfonyl hydrazide was used as a reagent for the preparation of tosylhydrazones. It was used to prepare dipyrazolo[1,5-a:4′,3′-c]pyridines and 1,2,3-selenadiazole derivatives.

Signal Word

Danger

Hazard Statements

H242,H301,H411

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2 - Self-react. D

Supplementary Hazards

EUH044

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Journal of the American Chemical Society, 114, 966-966 (1992)
Mousa Al-Smadi et al.
Molecules (Basel, Switzerland), 13(11), 2740-2749 (2008-11-07)
The commercially available aromatic polyketones 1a-d were utilized for the synthesis of the multi-arm1,2,3-selenadiazole derivatives 3a-d. The preparation starts with the reaction between compounds 1a-d and p-toluenesulfonyl hydrazide to give the corresponding tosylhydrazones 2a-d. Subsequent reaction with selenium dioxide leads
Wolfgang Holzer et al.
Beilstein journal of organic chemistry, 8, 2223-2229 (2013-02-01)
The synthesis of dipyrazolo[1,5-a:4',3'-c]pyridines is described. Easily obtainable 5-alkynylpyrazole-4-carbaldehydes, p-toluenesulfonyl hydrazide, and an aldehyde or ketone containing an α-hydrogen atom were reacted in a silver triflate catalyzed multicomponent reaction affording new tricyclic compounds with a dipyrazolo[1,5-a:4',3'-c]pyridine core. Detailed NMR spectroscopic
Journal of the American Chemical Society, 115, 2473-2473 (1993)
Anna V Gudmundsdottir et al.
Organic letters, 10(16), 3461-3463 (2008-07-12)
N'-Glycopyranosylsulfonohydrazides are introduced as glycosyl donors for protecting group free synthesis of O-glycosides, glycosyl azides, and oxazolines. Mono- and disaccharides containing a reducing terminal N-acetylglucosamine residue were condensed with p-toluenesulfonylhydrazide to give the desired beta- d-pyranose donors. These donors can
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