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p-Toluenesulfonyl hydrazide

Catalog No. A13529 Name Alfa Aesar
CAS Number 1576-35-8 Website
M. F. C7H10N2O2S Telephone
M. W. 186.2315 Fax
Purity 98% Email
Storage Chembase ID: 70112

SYNONYMS

Title
对甲苯磺酰肼
IUPAC name
4-methylbenzene-1-sulfonohydrazide
IUPAC Traditional name
4-toluenesulfonyl hydrazide
Synonyms
p-Toluenesulfonohydrazide
4-Methylbenzenesulfonyl hydrazide

DATABASE IDS

CAS Number 1576-35-8
MDL Number MFCD00007588
Beilstein Number 610130
EC Number 216-407-3

PROPERTIES

Purity 98%
Density 1.4
Melting Point 108-111°C
GHS Pictograms GHS02
GHS Pictograms GHS06
GHS Hazard statements H242-H228-H301
European Hazard Symbols X
European Hazard Symbols Flammable Flammable (F)
GHS Precautionary statements P210-P280F-P309-P310
Risk Statements 11-22-44
RTECS MW0210000
Safety Statements 7-16-36
TSCA Listed
Hazard Class 4.1
UN Number UN3226
Packing Group II

DETAILS

REFERENCES

  • 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).
  • 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).