4-methylbenzene-1-sulfonohydrazide

• ChemBase编号: 70112
• 分子式: C7H10N2O2S
• 平均质量: 186.2315
• 单一同位素质量: 186.04629857
• SMILES: c1(ccc(cc1)C)S(=O)(=O)NN
• Canonical SMILES: NNS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C7H10N2O2S/c1-6-2-4-7(5-3-6)12(10,11)9-8/h2-5,9H,8H2,1H3
• InChIKey: ICGLPKIVTVWCFT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-methylbenzene-1-sulfonohydrazide
• IUPAC传统名: 4-toluenesulfonyl hydrazide
• 别名: 4-甲苯磺酰肼; 发泡剂 TSH; 甲苯磺酰肼; 对甲苯磺酰肼; 对甲苯磺酰肼; 4-甲苯磺酰肼; p-Toluenesulfonic acid hydrazide; p-Toluenesulfonyl hydrazide; Tosylhydrazide; p-Toluenesulfonhydrazide; p-TOLUENESULFONYLHYDRAZINE; 4-Methylbenzenesulfonyl hydrazide; p-Toluenesulfonohydrazide; 4-Methylbenzenesulfonhydrazide; p-Toluenesulfonhydrazide; p-Toluenesulfonyl hydrazide

登记号

• CAS号: 1576-35-8
• EC号: 216-407-3
• MDL号: MFCD00007588
• Beilstein号: 610130
• PubChem SID: 162035837; 24847540
• PubChem CID: 15303

理论计算性质

• Acid pKa: 10.2463665
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 0.79622304
• LogD (pH = 7.4): 0.8005806
• Log P: 0.79622227
• 摩尔折射率: 47.7412 cm^3
• 极化性: 18.81267 Å^3
• 极化表面积: 72.19 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 熔点: 103-108 °C(lit.); 108-111°C
• 闪点: 140 °F; 60 °C
• 密度: 1.4

安全信息

• 保存注意事项: IRRITANT
• RTECS编号: MW0210000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); X; 有害性(Harmful) (Xn)
• 联合国危险货物编号: 3226; UN3226
• 德国WGK号: 3
• 联合国危险货物等级: 4.1
• 联合国危险货物包装类别(PG): II
• 危险公开号: 11-22; 11-22-44
• 安全公开号: 7-16-36
• TSCA收录: false; 是
• GHS危险品标识: GHS02; GHS06
• GHS警示词: Danger
• GHS危险声明: H242-H228-H301; H242-H301-H319
• GHS警示性声明: P210-P280F-P309-P310; P301 + P310-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3226 4.1

产品相关信息

• 纯度: ~99%; ≥95% (HPLC); 95+%; 97%; 98%
• 级别: technical
• 线性分子式: CH3C6H4SO2NHNH2

详细说明

MP Biomedicals - 05218793

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 132004

包装
25, 100, 500 g in poly bottle
Application
广泛用于制备甲苯磺酰腙。1,2,3,4

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).