Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

A13529 4-Methylbenzenesulphonylhydrazide, 98%

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

Stock No. Size Price ($) Quantity Availability
A13529-14 25g 23.50
A13529-22 100g 46.00
A13529-36 500g 170.00
Add to Cart Bulk/Specialty Print Quote View Item

4-Methylbenzenesulphonylhydrazide, 98%

MDL
MFCD00007588
EINECS
216-407-3

Chemical Properties

Formula
C7H10N2O2S
Formula Weight
186.23
Melting point
108-111°
Density
1.4
Storage & Sensitivity
Ambient temperatures.
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-H301-H319

Heating may cause a fire. Toxic if swallowed. Causes serious eye irritation.

Precautionary Statements: P210-P220-P234-P264b-P270-P280-P301+P310-P305+P351+P338-P330-P337+P313-P370+P378q-P375-P380-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep/Store away from clothing/combustible materials. Keep only in original container. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If eye irritation persists: Get medical advice/attention. In case of fire: Use CO2, dry chemical, or foam Fight fire remotely due to the risk of explosion. Evacuate area. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
610130
Hazard Class
4.1
Harmonized Tariff Code
2935.90
TSCA
Yes
RTECS
MW0210000

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware