LITHIUM TETRAMETHYLPIPERIDIDE

Product Name: LITHIUM TETRAMETHYLPIPERIDIDE
CAS No.: 38227-87-1
Chemical Name: LITHIUM TETRAMETHYLPIPERIDIDE
Synonyms: LiTMP;LTMP;LithiuM 2,2,6,6-tetraMethylpiperidide;Piperidine, 2,2,6,6-tetramethyl-, lithium salt;piperidide;ithium 2,2,6,6-tetramethyL;LITHIUM TETRAMETHYLPIPERIDIDE;2,2,6,6-Tetramethylpiperidyllithium;Lithium·2,2,6,6-tetramethylpiperidine;"2,2,6,6-tetramethylpiperidine lithium"
CBNumber: CB6365411
Molecular Formula: C9H18LiN
Formula Weight: 147.19
MOL File: 38227-87-1.mol

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LITHIUM TETRAMETHYLPIPERIDIDE Property

solubility: sol most organic solvents including THF, Et2O, hexane.
form: solid
InChI: InChI=1S/C9H18N.Li/c1-8(2)6-5-7-9(3,4)10-8;/h5-7H2,1-4H3;/q-1;+1
InChIKey: ANYSGBYRTLOUPO-UHFFFAOYSA-N
SMILES: C1CCC(C)(C)[N-]C1(C)C.[Li+]

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Safety

Hazard Codes: F,C
Risk Statements: 63-14/15-34-62
Safety Statements: 16-26-36/37/39-43-45
RIDADR: UN 3131 8(4.3) / PGII
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H261In contact with water releases flammable gas

H314Causes severe skin burns and eye damage

Precautionary statements

P231+P232Handle under inert gas. Protect from moisture.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P422Store contents under …

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 735353
Product name: Lithium 2,2,6,6-tetramethylpiperidide
Purity: 97%
Packaging: 10g
Price: $250
Updated: 2025/07/31

Sigma-Aldrich

Product number: 735353
Product name: Lithium 2,2,6,6-tetramethylpiperidide
Purity: 97%
Packaging: 25g
Price: $293
Updated: 2025/07/31

American Custom Chemicals Corporation

Product number: OGM0000655
Product name: LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE
Purity: 95.00%
Packaging: 25G
Price: $1275.81
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: OGM0000655
Product name: LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE
Purity: 95.00%
Packaging: 250G
Price: $2480.5
Updated: 2021/12/16

Aaron Chemicals

Product number: AR003RZO
Product name: Lithium 2,2,6,6-tetramethylpiperidide
Purity: 97%
Packaging: 1g
Price: $28
Updated: 2021/12/16

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LITHIUM TETRAMETHYLPIPERIDIDE Chemical Properties,Usage,Production

Physical properties

Lithium 2,2,6,6-Tetramethylpiperidide exists in THF solution as a dimer-monomer equilibrium mixture; additives such as HMPA increase monomer concentration. X-ray structure determination shows that LiTMP crystallizes as a tetramer from hexane/pentane mixtures.

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]

Application

Lithium 2,2,6,6-Tetramethylpiperidide (LTMP) is a strong, highly hindered, nonnucleophilic base (pKa = 37.3) capable of selective deprotonation of aromatics, heteroaromatics, and aliphatic C-H acidic sites in the presence of a variety of functional groups; also compatible with several electrophiles for in situ quenching of kinetically derived lithiated species.

Preparation

Preparative Method of Lithium 2,2,6,6-Tetramethylpiperidide: prepared in Et2O or THF solutions immediately before use by treatment of commercially available dry 2,2,6,6-Tetramethylpiperidine with n-Butyllithium (1:1). Tetramethylpiperidine is dried by heating a mixture of the base with CaH2 at reflux for 4 h in a preflamed flask, followed by distillation at atmospheric pressure (bp 152 °C). It should be stored in a septum sealed bottle.

storage

LiTMP solutions are pyrophoric, can cause severe burns, and should always be handled and transferred under an inert atmosphere. Solutions of LiTMP show a loss of activity (50% in THF; 60% in Et2O) after 12 h at 24 °C. Use in a fume hood.

LITHIUM TETRAMETHYLPIPERIDIDE Preparation Products And Raw materials

Raw materials

Preparation Products

3-BROMO-2-((CYCLOPROPYLAMINO)METHYL)BENZALDEHYDE

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LITHIUM TETRAMETHYLPIPERIDIDE Suppliers

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View Lastest Price from LITHIUM TETRAMETHYLPIPERIDIDE manufacturers

Shaanxi Dideu New Materials Co. Ltd

Product: LITHIUM TETRAMETHYLPIPERIDIDE 38227-87-1
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 10000KGS
Release date: 2025-05-23

38227-87-1, LITHIUM TETRAMETHYLPIPERIDIDERelated Search:

2,2,6,6-Tetramethylpiperidine 2,2,6,6-tetramethyl-4-piperidinol 2,2,6,6-Tetramethylpiperidinooxy 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 2,2,6,6-Tetramethylpiperidinylzinc chloride lithium chloride complex solution, 1.0 M in THF Triacetonamine 2,2,6,6-Tetramethyl-3,5-heptanedione Lithium amide LITHIUM DIMETHYLAMIDE LITHIUM TETRAMETHYLPIPERIDIDE Lithium diisopropylamide 2,2-dimethylpiperidine LITHIUM DIETHYLAMIDE

LITHIUM TETRAMETHYLPIPERIDIDE

Piperidine, 2,2,6,6-tetramethyl-, lithium salt

Lithium·2,2,6,6-tetramethylpiperidine

LithiuM 2,2,6,6-tetraMethylpiperidide

Piperidine,2,2,6,6-tetramethyl-, lithium salt (1:1)

LithiuM 2,2,6,6-tetraMethylpiperidide 97%

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

LTMP

LiTMP

ithium 2,2,6,6-tetramethyL

piperidide

"2,2,6,6-tetramethylpiperidine lithium"

Lithium 2,2,6,6-tetramethylpiperidin-1-ide

Lithium-2,2,6,6-tetramethylpiperidin-1-id

Lithium (N,N,N,N-tetramethylpiperidide)

Lithium 2,2,6,6-tetramethylpiperidide (1.0 M in THF)

2,2,6,6-Tetramethylpiperidyllithium

38227-87-1

C9H18LiN