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558087

Sigma-Aldrich

Acetophenone tosylhydrazone

97%

Synonym(s):

p-Toluenesulfonic acid (α-methylbenzylidene)hydrazide

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About This Item

Linear Formula:
C6H5C(CH3)=NNHSO2C6H4CH3
CAS Number:
4545-21-5
Molecular Weight:
288.36
MDL number:
MFCD01140191
UNSPSC Code:
12352100
PubChem Substance ID:
24879721

assay

97%

form

solid

mp

144-149 °C (lit.)

SMILES string

Cc1ccc(cc1)S(=O)(=O)N\N=C(/C)c2ccccc2

InChI

1S/C15H16N2O2S/c1-12-8-10-15(11-9-12)20(18,19)17-16-13(2)14-6-4-3-5-7-14/h3-11,17H,1-2H3/b16-13+

InChI key

MIXFDFCKBMCLGN-DTQAZKPQSA-N

General description

Acetophenone tosylhydrazone is formed as one of the reaction products from the reduction of phenacyl in the presence of tosyl hydrazide methanol solution.[1]

Application

Acetophenone tosylhydrazone may be used to synthesize ethylbenzene, via reduction with bis(benzoyloxy)borane.[2]

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
12918LO

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A mild and convenient conversion of ketones to the corresponding methylene derivatives via reduction of tosylhydrazones by bis (benzoyloxy) borane.
Kabalka GW and Summers ST.
The Journal of Organic Chemistry, 46(6), 1217-1218 (1981)
Synthesis of 1, 2, 3-Triazoles.
Dolly BB and Barba F.
Heterocycles, 63, 1175-1180 (2004)

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