CAS 2564-83-2|TEMPO|ol|1-Oxy-2,2,6,6-tetramethylpiperidine, free radical|ump 5'-end residue|TEMPO|tyrosine(.)|(2,2,6,6-Tetramethyl-piperidin-1-yl)oxyl|2,2,6,6-四甲基哌啶氧化物|2,2,6,6-Tetramethyl-1-...

General Information

Structure

Molecular Formula

C₉H₁₈NO

Molecular Mass

156.24532

Exact Mass

156.1388392

Charge

0

InChI

InChI=1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3

InChIKey

QYTDEUPAUMOIOP-UHFFFAOYSA-N

Canonic Smiles

[O]N1C(C)(C)CCCC1(C)C

Isomeric Smiles

N1(C(CCCC1(C)C)(C)C)[O]

Calculated Properties

JChem

LogD (pH = 7.4)

1.75

LogD (pH = 5.5)

1.75

Log P

1.75

Rotatable Bonds

0

H Donor

0

H Acceptors

2

Lipinski's Rule of Five

true

Acid pKa

0.71

Polar Surface Area

3.24

Polarizability

18.42

Molar Refractivity

45.59

LOG S

-1.91

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

TEMPO1-Oxy-2,2,6,6-tetramethylpiperidine, free radicalTEMPO(2,2,6,6-Tetramethyl-piperidin-1-yl)oxyl2,2,6,6-四甲基哌啶氧化物2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical2,2,6,6-四甲基哌啶-1-氧自由基2,2,6,6-Tetramethylpiperidine 1-oxylTEMPO2,2,6,6-Tetramethylpiperidine 1-Oxyl2,2,6,6-四甲基哌啶氧化物, 自由基2,2,6,6-四甲基哌啶氧化物2,2,6,6-Tetramethylpiperidine 1-oxylTEMPO, free radical1,1,5,5-tetramethylpentamethylene nitroxideTEMPO2,2,6,6-tetramethyl-1-piperidinyloxy2,2,6,6-tetramethylpiperidinooxy radical

IUPAC name

ol (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl

IUPAC Traditional name

ump 5'-end residue tyrosine(.) tanan

Names and Identifiers

Registration numbers

CAS Number

MDL Number

PubChem CID

CHEBI ID

Chemspider ID

CHEMBL

Wikipedia Title

Beilstein Number

EC Number

PubChem SID

2486669924852819248889681620771528147413

Merck Index

149140

PubMed Citation Links

3329620533483052339235273400996633225568

UniProt Database

Q3V6T2Q810H6Q98TY9Q811T9P60483Q9NRI5Q01314Q9PUT6P47196P47197Q5SNZ0P31750O08586Q60823Q45FX5P31751P31749P60484

ACToR Database

2564-83-2125012-91-1

SureChEMBL Database

SCHEMBL6492

CompTox Database

DTXSID2073300

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

TEMPO

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

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

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

ChEBI

CHEBI:32849

A member of the class of aminoxyls that is piperidine that carries an oxidanediyl group at position 1 and methyl groups at positions 2, 2, 6, and 6, respectively.

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

• Cf also 4-Hydroxy-TEMPO, A12497, and 4-Acetamido-TEMPO, B23456.

• For a review of the use of stable nitroxyl radicals for the oxidation of primary and secondary alcohols, see: Synthesis, 1153 (1996).

• 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).

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:90333