ol

• ChemBase ID: 90333
• Molecular Formular: C9H18NO
• Molecular Mass: 156.24532
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: ol
• IUPAC Traditional name: ump 5'-end residue; tyrosine(.)
• Synonyms: 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; 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

Database IDs

• CAS Number: 2564-83-2
• EC Number: 219-888-8
• MDL Number: MFCD00009599
• Beilstein Number: 1422418
• Merck Index: 149140
• PubChem SID: 162077152; 24852819; 24866699; 24888968
• PubChem CID: 2724126
• CHEBI ID: 32849
• CHEMBL: 606971
• Chemspider ID: 2006285
• Wikipedia Title: TEMPO

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.7549286
• LogD (pH = 7.4): 1.7549286
• Log P: 1.7549286
• Molar Refractivity: 45.5923 cm^3
• Polarizability: 18.29713 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 31-40°C; 36-38 °C(lit.); 36–38 °C; 36-39 °C; 36-39°C
• Boiling Point: 193°C dec.; sublimes under vacuum
• Flash Point: 152.6 °F; 67 °C; 67°C; 67°C(152°F)

Safety Information

• Storage Warning: Corrosive/Keep Cold
• RTECS: TN8991900
• European Hazard Symbols: Corrosive (C)
• UN Number: 3263; UN3263
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 34; R34
• Safety Statements: 26-36/37/39-45; 26-36/37/39-45-60; S26 S36/37/39 S45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (GC); 98%; 98+%; 99%
• Grade: purum
• Purified By: sublimation
• Empirical Formula (Hill Notation): C9H18NO

DETAILS

Sigma Aldrich - 214000

Application
Catalytic oxidant in the iodobenzene diacetae oxidation of nerol to neral.1
General description
Copper/TEMPO has been utilized in the catalytic oxidation of primary alcohols to aldehydes.2
Packaging
1, 5, 25 g in glass bottle

Sigma Aldrich - 426369

Application
Stable nitroxide radical useful in controlling living polymerizations
General description
For a synthetic protocol using NMP initiators, contributed by Prof. Karen Wooley, please visit our technology spotlight.
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 87903

Other Notes
Stable free radical used for radical trapping in mechanistic studies; TEMPO reacts preferentially with carbon-centered radicals1,2,3; Calalyst used in the oxidation of prim. alcohols to aldehydes with NaOCl4

REFERENCES

• 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.