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:

98%,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-piperidine

3-(lithiomethyl)pyridine

3-bromo-2-methylbenzoic acid

3,4-Methylenedioxybenzyl bromide

Refernces

• 1、 -. "UROKINASE INHIBITORS". . . Retrieved 2008/06/13.
• 2、 Fraser, Robert R.,Mansour, Tarek S.,Savard, Sylvain. "Acidity Measurements on Pyridines in Tetrahydrofuran Using Lithiated Silylamines". . p. 3232 - 3234. Retrieved 2007/10/02.