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Merck

735353

Lithium 2,2,6,6-tetramethylpiperidide

95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C9H18LiN
CAS Number:
38227-87-1
Molecular Weight:
147.19
NACRES:
NA.22
PubChem Substance ID:
329764934
UNSPSC Code:
12352005
MDL number:
MFCD00015910
Assay:
95%
Form:
solid

Key Documents

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InChI

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

SMILES string

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

InChI key

ANYSGBYRTLOUPO-UHFFFAOYSA-N

assay

95%

form

solid

Quality Level

100

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

signalword

Danger

hcodes

H261,H314

Storage Class

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

Hazard Classifications

Skin Corr. 1B - Water-react. 2

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.

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

fsl

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

jan

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN9624
SHBN8633
SHBK5689
SHBJ1900
SHBJ0171

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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)
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)
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
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)

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