Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

Safety Information

735353

Sigma-Aldrich

Lithium 2,2,6,6-tetramethylpiperidide

95%

Synonym(s):

2,2,6,6-Tetramethylpiperidine lithium salt (1:1), LTMP

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C9H18LiN
CAS Number:
38227-87-1
Molecular Weight:
147.19
MDL number:
MFCD00015910
UNSPSC Code:
12352005
PubChem Substance ID:
329764934
NACRES:
NA.22

Quality Level

100

Assay

95%

form

solid

SMILES string

[Li]N1C(C)(C)CCCC1(C)C

InChI

1S/C9H18N.Li/c1-8(2)6-5-7-9(3,4)10-8;/h5-7H2,1-4H3;/q-1;+1

InChI key

ANYSGBYRTLOUPO-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

Application

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]

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H261,H314

Hazard Classifications

Skin Corr. 1B - Water-react 2

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank I
1st spontaneously combustible materials and water reactive materials

JAN Code

735353-25G:
735353-VAR:
735353-BULK:
735353-10G:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBR2103
SHBQ7870
SHBP5731
SHBP3791
SHBP4204

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Case for Lithium Tetramethylpiperidide-Mediated Ortholithiations: Reactivity and Mechanisms.
Mack KA and Collum DB
Journal of the American Chemical Society, 140(14), 4877-4883 (2018)
Alkenes from terminal epoxides using lithium 2,2,6,6-tetramethylpiperidide and organolithiums or grignard reagents.
Hodgson DM, et al.
Journal of the American Chemical Society, 126(39), 12250-12251 (2004)
Deprotonative metalation of methoxy-substituted arenes using lithium 2, 2, 6, 6-tetramethylpiperidide: Experimental and computational study.
Akimoto G, et al.
The Journal of Organic Chemistry, 83(21), 13498-13506 (2018)
Martin-Louis Y Riu et al.
Science advances, 6(13), eaaz3168-eaaz3168 (2020-04-02)
This exploratory synthesis investigation was undertaken to determine the viability of replacing a single carbon vertex with another p-block element in a highly strained tetrahedrane molecule. Phosphorus was selected for this purpose because the stable molecular form of elemental phosphorus

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service