ol

• ChemBase编号: 90333
• 分子式: C9H18NO
• 平均质量: 156.24532
• 单一同位素质量: 156.1388392
• SMILES: N1(C(CCCC1(C)C)(C)C)[O]
• Canonical SMILES: [O]N1C(C)(C)CCCC1(C)C
• InChI: InChI=1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3
• InChIKey: QYTDEUPAUMOIOP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ol
• IUPAC传统名: ump 5'-end residue; tyrosine(.)
• 别名: 2,2,6,6-四甲基哌啶-1-氧自由基; 2,2,6,6-四甲基哌啶氧化物; 2,2,6,6-四甲基哌啶氧化物; 2,2,6,6-四甲基哌啶氧化物, 自由基; 2,2,6,6-Tetramethylpiperidine 1-Oxyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical; 2,2,6,6-Tetramethylpiperidine 1-oxyl; TEMPO; TEMPO; 1-Oxy-2,2,6,6-tetramethylpiperidine, free radical; (2,2,6,6-Tetramethyl-piperidin-1-yl)oxyl; TEMPO; 2,2,6,6-Tetramethylpiperidine 1-oxyl; TEMPO, free radical

登记号

• CAS号: 2564-83-2
• EC号: 219-888-8
• MDL号: MFCD00009599
• Beilstein号: 1422418
• 默克索引号: 149140
• PubChem SID: 24852819; 24866699; 24888968; 162077152
• PubChem CID: 2724126
• CHEBI ID: 32849
• CHEMBL: 606971
• Chemspider ID: 2006285
• 维基百科标题: TEMPO

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.7549286
• LogD (pH = 7.4): 1.7549286
• Log P: 1.7549286
• 摩尔折射率: 45.5923 cm^3
• 极化性: 18.29713 Å^3
• 极化表面积: 3.24 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

• 熔点: 31-40°C; 36-38 °C(lit.); 36–38 °C; 36-39 °C; 36-39°C
• 沸点: 193°C dec.; sublimes under vacuum
• 闪点: 152.6 °F; 67 °C; 67°C; 67°C(152°F)

安全信息

• 保存注意事项: Corrosive/Keep Cold
• RTECS编号: TN8991900
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C)
• 联合国危险货物编号: 3263; UN3263
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; III
• 危险公开号: 34; R34
• 安全公开号: 26-36/37/39-45; 26-36/37/39-45-60; S26 S36/37/39 S45
• TSCA收录: 是
• GHS危险品标识: GHS05
• GHS警示词: Danger
• GHS危险声明: H314; H314-H318
• GHS警示性声明: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• 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 3263 8/PG 2
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥96.0% (GC); 98%; 98+%; 99%
• 级别: purum
• 提纯方法: sublimation
• Empirical Formula (Hill Notation): C9H18NO

详细说明

Sigma Aldrich - 214000

Application
用于将橙花醇经碘苯二乙酸氧化为橙花醛的催化氧化剂。1
General description
铜/TEMPO 已用于将伯醇催化氧化为醛。2
包装
1, 5, 25 g in glass bottle

Sigma Aldrich - 426369

Application
稳定的氮氧自由基，用于控制活性聚合反应
General description
想了解 Karen Wooley 教授提供的采用 NMP 引发剂的合成方案，请访问 技术聚焦。
包装
1, 5 g in glass bottle

Sigma Aldrich - 87903

Other Notes
稳定的自由基，用于自由基捕捉机理研究；TEMPO 优先与以碳为中心的自由基反应1,2,3；催化剂，用于通过 NaOCl 将伯醇氧化为醛4

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.