2,2,6,6-四甲基哌啶氧化物, 自由基

• 产品号: A12733
• CAS号: 2564-83-2
• 分子式: C9H18NO
• 分子量: 156.24532
• 纯 度: 98+%

产品别名

• 标题: TEMPO, free radical
• IUPAC标准名: ol
• IUPAC传统名: tyrosine(.)
• 别名: 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical

产品登记号

• EC号: 219-888-8
• 默克索引号: 149140
• MDL号: MFCD00009599
• CAS号: 2564-83-2
• Beilstein号: 1422418

产品性质

• 纯度: 98+%
• 沸点: 193°C dec.
• 闪点: 67°C(152°F)
• 熔点: 31-40°C
• GHS危险声明: H314-H318
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• GHS警示性声明: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• 危险公开号: 34
• RTECS编号: TN8991900
• 安全公开号: 26-36/37/39-45-60
• TSCA收录: 是
• 联合国危险货物等级: 8
• 联合国危险货物编号: UN3263
• 联合国危险货物包装类别(PG): III

参考文献

• For brief features on TEMPO and related reagents, see: Synlett, 563 (2001); 1757 (2003); 657 (2006). For reviews on nitroxide radicals, see: Synthesis, 190, 401 (1971); Chem. Rev., 78, 37 (1978); J. Sci. Ind. Res., 54, 623 (1995).
• In the presence of a catalytic amount of KBr, catalyzes the selective oxidation of primary and secondary alcohols to aldehydes and ketones by buffered NaOCl: J. Org. Chem., 50, 4888 (1985); 52, 2559 (1987); Org. Synth. Coll., 8, 367 (1993). High yields of aldehydes can also be obtained under mild, phase-transfer conditions with Oxone.: Org. Lett., 2, 1173 (2000). In the presence of CuCl, aerobic oxidation of alcohols to aldehydes and ketones has been accomplished in the ionic liquid 1-n-Butyl-3-methylimidazolium hexafluorophosphate, L19086: Org. Lett., 4, 1507 (2002). With NaOCl, ɑ-amino or ɑ-alkoxy alcohols have also been oxidized to the aldehydes: Tetrahedron Lett., 33, 5029 (1992). The use of I₂ as cooxidant is useful for sensitive substrates: Org. Lett., 5, 235 (2003).
• The addition of quaternary salts to the reaction mixture permits further oxidation of aldehydes to acids. Selective oxidation of a primary OH to an aldehyde can be achieved in the presence of a secondary OH: J. Org. Chem., 54, 2970 (1989); Tetrahedron Lett., 31, 2177 (1990). The oxidation can also be performed using NCS under phase-transfer conditions: J. Org. Chem., 61, 7452 (1996), with Iodosobenzene diacetate, B24531: J. Org. Chem., 62, 6974 (1997), or Trichloroisocyanuric acid, B23906: Org. Lett., 3, 3041 (2001).
• For a review of the use of stable nitroxyl radicals for the oxidation of primary and secondary alcohols, see: Synthesis, 1153 (1996).
• Cf also 4-Hydroxy-TEMPO, A12497, and 4-Acetamido-TEMPO, B23456.