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
LITHIUM TETRAMETHYLPIPERIDIDE Property
- solubility
- sol most organic solvents including THF, Et2O, hexane.
- form
- solid
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
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 …
N-Bromosuccinimide Price
- Product number
- 735353
- Product name
- Lithium 2,2,6,6-tetramethylpiperidide
- Purity
- 97%
- Packaging
- 10g
- Price
- $243
- Updated
- 2024/03/01
- Product number
- 735353
- Product name
- Lithium 2,2,6,6-tetramethylpiperidide
- Purity
- 97%
- Packaging
- 25g
- Price
- $284
- Updated
- 2024/03/01
- Product number
- OGM0000655
- Product name
- LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE
- Purity
- 95.00%
- Packaging
- 25G
- Price
- $1275.81
- Updated
- 2021/12/16
- Product number
- OGM0000655
- Product name
- LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE
- Purity
- 95.00%
- Packaging
- 250G
- Price
- $2480.5
- Updated
- 2021/12/16
- Product number
- AR003RZO
- Product name
- Lithium 2,2,6,6-tetramethylpiperidide
- Purity
- 97%
- Packaging
- 1g
- Price
- $28
- Updated
- 2021/12/16
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
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