2-methyl-1H-indole

• ChemBase编号: 69515
• 分子式: C9H9N
• 平均质量: 131.17446
• 单一同位素质量: 131.07349929
• SMILES: [nH]1c(cc2ccccc12)C
• Canonical SMILES: Cc1cc2c([nH]1)cccc2
• InChI: InChI=1S/C9H9N/c1-7-6-8-4-2-3-5-9(8)10-7/h2-6,10H,1H3
• InChIKey: BHNHHSOHWZKFOX-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-methyl-1H-indole
• IUPAC传统名: 2-methylindole
• 别名: 2-甲基吲哚; NSC 7514; 2-Methylindole; 2-Methylindole

登记号

• CAS号: 95-20-5
• EC号: 202-398-3
• MDL号: MFCD00005616
• Beilstein号: 109781
• PubChem SID: 162035241; 24896980
• PubChem CID: 7224
• CHEMBL: 259419
• Chemspider ID: 6954
• 维基百科标题: 2-Methylindole

理论计算性质

• Acid pKa: 16.616098
• 质子受体: 0
• 质子供体: 1
• LogD (pH = 5.5): 2.271569
• LogD (pH = 7.4): 2.271569
• Log P: 2.271569
• 摩尔折射率: 42.2942 cm^3
• 极化性: 17.424286 Å^3
• 极化表面积: 15.79 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Yellow viscous liquid
• 熔点: 56-60°C; 57-59 °C(lit.); 58-60°C
• 沸点: 272-273°C; 273 °C(lit.); 273°C
• 闪点: 141 °C; 141°C(285°F); 285.8 °F
• 密度: 1.07

安全信息

• 保存注意事项: IRRITANT; Light Sensitive
• RTECS编号: NM0345000
• 欧盟危险性物质标志: X; 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 22; 41
• 安全公开号: 26-39; 36
• TSCA收录: false; 是
• GHS危险品标识: GHS05; GHS06
• GHS警示词: Danger
• GHS危险声明: H301; H318
• GHS警示性声明: P264-P270-P301+P310-P321-P405-P501A; P280-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: 95+%; 98%; 98+%
• Empirical Formula (Hill Notation): C9H9N

详细说明

MP Biomedicals - 05205484

MP Biomedicals Rare Chemical collection

Sigma Aldrich - M51407

包装
25, 100 g in glass bottle
Application
Reactant for:
• Regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition reaction1
• Friedel-Crafts alkylation reactions2
• Preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators3
• Preparation of plant-growth inhibitors4
• Michael addition reactions5
• Synthesis of cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors6

参考文献

• Can be dimetallated using the n-BuLi/KO-t-Bu system. Reaction with electrophiles (methyl iodide, benzophenone, t-butyl isocyanate) then occurs preferentially at the more reactive methyl position: J. Chem. Soc., Perkin 1, 179 (1990).
• An alternative approach to functionalization of the 2-methyl group involves low-temperature N-lithiation followed by reaction with dimethyl carbonate to give the 1-methoxycarbonyl derivative. NBS ɑ-bromination then allows nucleophilic substitution to give a variety of 2-substituted indoles: Synthesis, 743 (1992).
• Undergoes a mild, selective C-3 reductive alkylation in the presence of Triethylsilane, A10320, and TFA; e.g. with benzaldehyde, the 3-benzyl derivative is formed in 88% yield: Tetrahedron Lett., 34, 1529 (1993).