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768-66-1,MFCD00005985
Catalog No.:AA0032TP

768-66-1 | 2,2,6,6-Tetramethylpiperidine

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5g
98%
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$10.00   $7.00
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10g
98%
in stock  
$16.00   $11.00
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25g
98%
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$19.00   $13.00
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100g
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500g
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0032TP
Chemical Name:
2,2,6,6-Tetramethylpiperidine
CAS Number:
768-66-1
Molecular Formula:
C9H19N
Molecular Weight:
141.2539
MDL Number:
MFCD00005985
SMILES:
CC1(C)CCCC(N1)(C)C
NSC Number:
102838
Properties
Properties
 
BP:
152°C at 760 mmHg  
Form:
Liquid  
MP:
-59 °C  
Refractive Index:
n20/D 1.445(lit.)  
Solubility:
MISCIBLE  
Stability:
Air Sensitive  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
111  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
XLogP3:
2.1  

Literature

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Journal: Dalton transactions (Cambridge, England : 2003) 20120814

Title: Simple and highly sensitive measurement method for detection of glass transition temperatures of polymers: application of ESR power saturation phenomenon with conventional spin-probe technique.

Journal: The journal of physical chemistry. B 20120802

Title: Design, synthesis, and antiviral activity of entry inhibitors that target the CD4-binding site of HIV-1.

Journal: Journal of medicinal chemistry 20120524

Title: Dynamic nuclear polarization of electron-beam irradiated polyethylene by pairs of alkyl free radicals.

Journal: Journal of magnetic resonance (San Diego, Calif. : 1997) 20120501

Title: Synthesis and biological evaluation of quinazoline and quinoline bearing 2,2,6,6-tetramethylpiperidine-N-oxyl as potential epidermal growth factor receptor(EGFR) tyrosine kinase inhibitors and EPR bio-probe agents.

Journal: European journal of medicinal chemistry 20120301

Title: [Development of versatile oxidation systems based on the design of oxoammonium salts].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20120101

Title: Structurally powered synergic 2,2,6,6-tetramethylpiperidine bimetallics: new reflections through lithium-mediated ortho aluminations.

Journal: Inorganic chemistry 20111219

Title: Pure forms of the singlet oxygen sensors TEMP and TEMPD do not inhibit Photosystem II.

Journal: Biochimica et biophysica acta 20111201

Title: Amination of benzoxazoles and 1,3,4-oxadiazoles using 2,2,6,6-tetramethylpiperidine-N-oxoammonium tetrafluoroborate as an organic oxidant.

Journal: Angewandte Chemie (International ed. in English) 20111125

Title: Reactivity of bacterial and fungal laccases with lignin under alkaline conditions.

Journal: Bioresource technology 20111101

Title: N-(1-Acryloyl-2,2,6,6-tetra-methyl-piperidin-4-yl)acryl-amide.

Journal: Acta crystallographica. Section E, Structure reports online 20111101

Title: Hydrogen atom abstraction selectivity in the reactions of alkylamines with the benzyloxyl and cumyloxyl radicals. The importance of structure and of substrate radical hydrogen bonding.

Journal: Journal of the American Chemical Society 20111019

Title: Azo dye decolorization by a laccase/mediator system in a membrane reactor: enzyme and mediator reusability.

Journal: Enzyme and microbial technology 20111010

Title: Reevaluation of analytical methods for photogenerated singlet oxygen.

Journal: Journal of clinical biochemistry and nutrition 20110901

Title: Syntheses of chloroisosulochrin and isosulochrin and biomimetic elaboration to maldoxin, maldoxone, dihydromaldoxin, and dechlorodihydromaldoxin.

Journal: Organic letters 20110819

Title: Evidence of singlet oxygen and hydroxyl radical formation in aqueous goethite suspension using spin-trapping electron paramagnetic resonance (EPR).

Journal: Chemosphere 20110801

Title: Inhibition of Photosystem II by the singlet oxygen sensor compounds TEMP and TEMPD.

Journal: Biochimica et biophysica acta 20110301

Title: Selective magnesiation or zincation of highly functionalized alkenes and cycloalkenes using 2,2,6,6-tetramethylpiperidyl bases.

Journal: Angewandte Chemie (International ed. in English) 20110218

Title: Reversible, metal-free hydrogen activation by frustrated Lewis pairs.

Journal: Dalton transactions (Cambridge, England : 2003) 20110207

Title: Design, synthesis and photostability of novel 1,8-naphthalimide PAMAM light-harvesting dendrons.

Journal: Journal of fluorescence 20110101

Title: Reactions of nitroxides. Part X: antifungal activity of selected sulfur and selenium derivatives of 2,2,6,6-tetramethylpiperidine.

Journal: Bioorganic & medicinal chemistry letters 20110101

Title: Use of mixed Li/K metal TMP amide (LiNK chemistry) for the synthesis of [2.2]metacyclophanes.

Journal: Beilstein journal of organic chemistry 20110101

Title: Frequency dependent study of the correlation functions in EPR spectroscopy--The Cole-Davidson approach. II. 2,N-(4-n-Butyl benzilidene) 4-amino 2,2,6,6-tetramethyl piperidine 1-oxide in toluene.

Journal: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20101101

Title: The influence of pre-emptive analgesia on postoperative analgesia and its objective evaluation.

Journal: Archives of medical science : AMS 20101001

Title: Tandem frustrated Lewis pair/tris(pentafluorophenyl)borane-catalyzed deoxygenative hydrosilylation of carbon dioxide.

Journal: Journal of the American Chemical Society 20100811

Title: Mesoscale spatial distribution of electron spins studied by time-resolved small-angle and ultrasmall-angle neutron scattering with dynamic nuclear polarization: a case of 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) doped in high-density polyethylene.

Journal: The Journal of chemical physics 20100807

Title: Lithium cadmate-mediated deprotonative metalation of anisole: experimental and computational study.

Journal: The Journal of organic chemistry 20100507

Title: Diisopropylamide and TMP turbo-Grignard reagents: a structural rationale for their contrasting reactivities.

Journal: Angewandte Chemie (International ed. in English) 20100419

Title: Novel bis-2,2,6,6-tetramethylpiperidine (bis-TMP) and bis-mecamylamine antagonists at neuronal nicotinic receptors mediating nicotine-evoked dopamine release.

Journal: Bioorganic & medicinal chemistry letters 20100215

Title: Hand-held mass spectrometer for environmentally relevant analytes using a variety of sampling and ionization methods.

Journal: European journal of mass spectrometry (Chichester, England) 20100101

Title: Pneumocystis cell wall beta-glucan stimulates calcium-dependent signaling of IL-8 secretion by human airway epithelial cells.

Journal: Respiratory research 20100101

Title: 2,2,6,6-Tetra-methyl-piperidinium triisopropoxysilanethiol-ate.

Journal: Acta crystallographica. Section E, Structure reports online 20091101

Title: Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20091005

Title: Photoreduction of oxoisoaporphines by amines: laser flash and steady-state photolysis, pulse radiolysis, and TD-DFT studies.

Journal: The journal of physical chemistry. A 20090709

Title: Alkyl-substituted amides as ligands in homometallic and heterobimetallic calcium complexes.

Journal: Inorganic chemistry 20090105

Title: Regio- and chemoselective metalation of chloropyrimidine derivatives with TMPMgCl x LiCl and TMP(2)Zn x 2 MgCl(2) x 2 LiCl.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20090101

Title: Using a two-step hydride transfer to achieve 1,4-reduction in the catalytic hydrogenation of an acyl pyridinium cation.

Journal: The Journal of organic chemistry 20081219

Title: 2,2,6,6-tetramethylpiperidinogallium as a terminal and bridging ligand in homo- and heteroleptic chromium, nickel, and cobalt complexes.

Journal: Inorganic chemistry 20081201

Title: Diffusion of 2,2,6,6-tetramethylpiperidine 1-oxyl derivatives of variable hydrophobicity in tropocollagen I solution.

Journal: Bioelectrochemistry (Amsterdam, Netherlands) 20081101

Title: Molecular tweezers for hydrogen: synthesis, characterization, and reactivity.

Journal: Journal of the American Chemical Society 20081029

Title: 2,2,6,6-Tetra-methyl-piperidinium penta-chloro-benzene-thiol-ate.

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Title: A 140 GHz prepolarizer for dissolution dynamic nuclear polarization.

Journal: The Journal of chemical physics 20080628

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Title: Antimicrobial activities of seven novel tetramethylpiperidine-substituted phenazines against multiple-drug-resistant Gram-positive bacteria.

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Title: Enantioselective enol lactone synthesis under double catalytic conditions.

Journal: Organic letters 20050317

Title: Conversion of the 2,2,6,6-tetramethylpiperidine moiety to a 2,2-dimethylpyrrolidine by cytochrome P450: evidence for a mechanism involving nitroxide radicals and heme iron.

Journal: Biochemistry 20040511

Title: Scavenging of reactive oxygen species by N-substituted indole-2 and 3-carboxamides.

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Title: A novel P450-catalyzed transformation of the 2,2,6,6-tetramethyl piperidine moiety to a 2,2-dimethyl pyrrolidine in human liver microsomes: characterization by high resolution quadrupole-time-of-flight mass spectrometry and 1H-NMR.

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Title: Carbolithiation of aromatic rings: cyclohexadienes from N-aroyl-2,2,6,6-tetramethylpiperidines.

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Title: Synthesis and properties of adducts of a hindered amine and 2-hydroxyphenylbenzotriazole as novel polymer stabilizers.

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Application
2,2,6,6-Tetramethylpiperidine serves as a versatile reactant in organic synthesis, offering a wide array of synthetic pathways. Its significance is evident in its role in various transformations, enabling the synthesis of diverse functional groups and compounds. Firstly, it participates in the allylic amination of allylic chlorides, facilitating the synthesis of allylated tertiary amines, a valuable class of compounds in organic chemistry. Additionally, it serves as a precursor in the oxidation reactions to yield hydroxylamines, essential intermediates in organic synthesis, using oxone as an oxidant. Furthermore, 2,2,6,6-Tetramethylpiperidine reacts with heterocyclic thiols in the presence of iodine as an oxidant to afford sulfenamide compounds, expanding its utility in sulfur-containing compound synthesis. Moreover, it enables the N-methylation of amines by reacting with CO2 and phenylsilane, providing a route to N-methylated amines, crucial building blocks in pharmaceutical and chemical industries. Lastly, it participates in three-component Mannich coupling reactions with aldehydes and alkynes to yield propargylamines, demonstrating its role in multi-component coupling reactions. With its diverse applications and synthetic capabilities, 2,2,6,6-Tetramethylpiperidine emerges as a valuable reagent in the toolbox of synthetic chemists for the construction of complex organic molecules.
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Tags:768-66-1 Molecular Formula|768-66-1 MDL|768-66-1 SMILES|768-66-1 2,2,6,6-Tetramethylpiperidine |Organic_Building_Blocks