Lithium tetramethylpiperidide

Base Information

• Chemical Name: Lithium tetramethylpiperidide
• CAS No.: 38227-87-1
• Molecular Formula: C9H19 N . Li
• Molecular Weight: 147.19
• Hs Code.: 2933399090
• European Community (EC) Number: 684-475-5
• DSSTox Substance ID: DTXSID00453330
• Nikkaji Number: J341.230J
• Wikipedia: Lithium_tetramethylpiperidide
• Wikidata: Q1110352
• Mol file: 38227-87-1.mol

Synonyms:lithium 2,2,6,6-tetramethylpiperidide

Chemical Property of Lithium tetramethylpiperidide

Chemical Property:

• PSA: 0.00000
• LogP: 2.43170
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 147.15992801
• Heavy Atom Count: 11
• Complexity: 116

Purity/Quality:

99%, ^*data from raw suppliers

Lithium 2,2,6,6-tetramethylpiperidide 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,C
• Statements: 63-14/15-34-62
• Safety Statements: 16-26-36/37/39-43-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [Li+].CC1(CCCC([N-]1)(C)C)C
• Uses: Lithium 2,2,6,6-tetramethylpiperidide is a strong base and can be used:For the synthesis of enamines from terminal epoxides through trans-α-lithiated epoxide as an intermediate.For ortholithiation of arenes such as 1,3-bis(trifluoromethyl)benzene, 4,4-dimethyl-2-phenyl-2-oxazoline, 1,4-bis(trifluoromethyl)benzene and 1,3-dimethoxybenzene.In combination with Lewis donor ligand, N,N,N′,N′-tetramethylethylenediamine (TMEDA) for deprotonative metalation of methoxy-substituted arenes.{21]

Technology Process of Lithium tetramethylpiperidide

There total 8 articles about Lithium tetramethylpiperidide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ 2,2,6,6-tetramethylpiperidinyl-lithium (38227-87-1) + lithium diisopropyl amide (4111-54-0)

Guidance literature:

Reference yield:

2,2,6,6-tetramethyl-piperidine (768-66-1) + lithium diisopropyl amide (4111-54-0) → 2,2,6,6-tetramethylpiperidinyl-lithium (38227-87-1) + diisopropylamine (108-18-9)

Guidance literature:

In tetrahydrofuran; at -47 ℃; Equilibrium constant;

DOI:10.1016/S0040-4039(00)88702-X

Reference yield:

2,2,6,6-tetramethyl-piperidine (768-66-1) + 3-(lithiomethyl)pyridine (26954-24-5) → 3-Methylpyridine (108-99-6) + 2,2,6,6-tetramethylpiperidinyl-lithium (38227-87-1)

Guidance literature:

In tetrahydrofuran; diethyl ether; at 27 ℃; Equilibrium constant;

DOI:10.1021/jo00217a050

upstream raw materials:

2,2,6,6-tetramethyl-piperidine

lithium diisopropyl amide

3-(lithiomethyl)pyridine

(4,4'-Dimethyldiphenylmethyl)lithium

Downstream raw materials:

2,2,6,6-tetramethyl-1-phenylpiperidine

2,2,6,6-tetramethyl-piperidine

3-(lithiomethyl)pyridine

N-trimethylsilylimidophosphenous acid 2,2,6,6-tetramethylpiperidine

Refernces

45. Total Synthesis of (+/-)-α-Acoradiene via Intramolecular Photoaddition and Reductive Cyclobutane Cleavage

10.1002/hlca.19830660213

The research details the total synthesis of (k)-a-acoradiene (4) from 3-methoxy-2-cyclohexenone through an 8-step process. The key steps involve a regio- and stereoselective photo [2 + 2] addition and reductive fragmentation. The purpose of the study was to develop a new, stereoselective approach to synthesizing the spiro [4.5] decane system, specifically targeting (k)-a-acoradiene. The researchers used key chemicals such as 3-methoxy-2-cyclohexenone, lithium/sodium alloy, t-butyl hydroperoxide, and lithium in ammonia. They also employed various reagents like N-chlorosuccinimide, dimethyl sulfide, and lithium tetramethylpiperidide. The conclusions drawn from the study confirmed the feasibility of the intramolecular photoaddition/cyclobutane fragmentation sequence for synthesizing complex structures like (k)-a-acoradiene. The researchers successfully synthesized the target compound and provided detailed structural evidence through spectral analysis.

N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides

10.1039/c1ob05267e

The research investigates the deprotonative metallation of N-aryl and N-heteroaryl pyrazoles using a mixed lithium–zinc base derived from ZnCl2·TMEDA (Zinc chloride N,N,N',N'-tetramethylethylenediamine complex) and LiTMP (Lithium 2,2,6,6-tetramethylpiperidide). The study explores the impact of various substituents on the pyrazole ring's CH acidity and how these influence the metallation outcomes. Through experimental and computational methods, including Density Functional Theory (DFT) calculations, the researchers determined the CH acidities of the substrates in both the gas phase and THF solution. They found that electron-withdrawing groups enhance CH acidity, favoring deprotonation, while electron-donating groups have the opposite effect. The results showed that the most acidic site on the pyrazole ring is typically the 5 position, and the study identified conditions under which mono-, di-, or tri-iodides could be selectively obtained.

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