对甲苯磺酰肼

• 产品号: A13529
• CAS号: 1576-35-8
• 分子式: C7H10N2O2S
• 分子量: 186.2315
• 纯 度: 98%

产品别名

• 标题: p-Toluenesulfonyl hydrazide
• IUPAC标准名: 4-methylbenzene-1-sulfonohydrazide
• IUPAC传统名: 4-toluenesulfonyl hydrazide
• 别名: p-Toluenesulfonohydrazide; 4-Methylbenzenesulfonyl hydrazide

产品登记号

• CAS号: 1576-35-8
• MDL号: MFCD00007588
• Beilstein号: 610130
• EC号: 216-407-3

产品性质

• 纯度: 98%
• 密度: 1.4
• 熔点: 108-111°C
• GHS危险声明: H242-H228-H301
• 欧盟危险性物质标志: X
• 欧盟危险性物质标志: 易燃性(Flammable) (F)
• GHS警示性声明: P210-P280F-P309-P310
• 危险公开号: 11-22-44
• RTECS编号: MW0210000
• 安全公开号: 7-16-36
• TSCA收录: 是
• 联合国危险货物等级: 4.1
• 联合国危险货物编号: UN3226
• 联合国危险货物包装类别(PG): II

参考文献

• 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).