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1576-35-8 - p-Toluenesulfonyl hydrazide, 98% - 4-Methylbenzenesulfonyl hydrazide - p-Toluenesulfonohydrazide - A13529 - Alfa Aesar

A13529 p-Toluenesulfonyl hydrazide, 98%

CAS Number
1576-35-8
Synonyms
4-Methylbenzenesulfonyl hydrazide
p-Toluenesulfonohydrazide

Size Price ($) Quantity Availability
25g 20.07
100g 43.57
500g 148.50
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p-Toluenesulfonyl hydrazide, 98%

MDL
MFCD00007588
EINECS
216-407-3

Chemical Properties

Formula
C7H10N2O2S
Formula Weight
186.23
Melting point
108-111°
Density
1.4
Solubility
Soluble in water, alcohol.

Applications

p-Toluenesulfonyl hydrazide is 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.

Notes

Store away from strong oxidizing agents. Keep container tightly closed. Store in cool, dry conditions in well sealed containers.

Literature References

Robert O. Hutchins.; Bruce Maryanoff.; Cynthia Milewski. Selective reduction of aliphatic ketones and aldehydes to hydrocarbons with sodium cyanoborohydride and p-toluenesulfonyl hydrazide in dimethylformamide-sulfolane. J. Am. Chem. Soc. 1971, 93, (7), 1793-1794.

Panagiotis Dounis.; James Feast, W. A route to low polydispersity linear and star polyethylenes via ring-opening metathesis polymerization. Polymer. 1996, 37, (12), 2547-2554.

Precursor of the versatile synthetic intermediates, tosylhydrazones. For a brief feature on tosylhydrazones, see: Synlett, 1844 (1999). Preparation using AcOH rather than mineral acid was found to reduce azine formation: Synthesis, 957 (1984).

Several simple methods are known for cleavage of tosylhydrazones, including:

Exchange with refluxing acetone: J. Org. Chem., 40, 3302 (1975); acetone/ BF3 etherate: Synthesis, 456 (1976); Amberlyst® 15 in aqueous acetone: J. Chem. Soc., Perkin 1, 2563 (1988).

Reduction of tosylhydrazones to alkanes by NaBH4 is a mild alternative to the Clemmensen and Wolff-Kishner methods: Chem. Ind. (London), 153, 1689 (1964). NaBH4 in AcOH is a more selective system: J. Org. Chem., 43, 2299 (1978). For reduction of a steroidal ketone by catecholborane, see: Org. Synth. Coll., 6, 293 (1988). Aliphatic tosylhydrazones are also reduced to methylenes by NaBH3CN, effective even for hindered ketones. For a study of the mechanism of this reduction, see: J. Org. Chem., 54, 4175 (1989).

Reaction of tosylhydrazones with base leads to alkenes (Bamford-Stevens reaction): J. Chem. Soc., 4735 (1952). Dianion formation from the tosylhydrazone with an alkyllithium or LDA results in a vinyllithium intermediate, which, on protonation, also gives the alkene (Shapiro-Heath reaction). With unsymmetrical tosylhydrazones, this is a useful synthesis of the less-substituted of the two possible alkenes: J. Am. Chem. Soc., 89, 5734 (1967); J. Org. Chem., 43, 1404 (1978):

For a reviews of the Bamford-Stevens, Shapiro-Heath and related reactions, see: Org. React., 23, 405 (1976); 39, 1 (1990). For an example (bornene: 63-66% yield from camphor tosylhydrazone and MeLi), see: Org. Synth. Coll., 6, 172 (1988).

GHS Hazard and Precautionary Statements

Hazard Statements: H242-H228-H301

Heating may cause a fire. Flammable solid. Toxic if swallowed.

Precautionary Statements: P210-P280f-P309-P310

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective clothing. IF exposed or if you feel unwell: Immediately call a POISON CENTER or doctor/physician.

Other References

Beilstein
610130
Hazard Class
4.1
Packing Group
II
Harmonized Tariff Code
2935.00
TSCA
Yes
RTECS
MW0210000

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