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Lithium tetramethylpiperidide manufacturers
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| | Lithium tetramethylpiperidide Basic information |
| Product Name: | Lithium tetramethylpiperidide | | Synonyms: | Piperidine, 2,2,6,6-tetramethyl-, lithium salt;Lithium·2,2,6,6-tetramethylpiperidine;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);ithium 2,2,6,6-tetramethyL;piperidide;"2,2,6,6-tetramethylpiperidine lithium" | | CAS: | 38227-87-1 | | MF: | C9H18LiN | | MW: | 147.19 | | EINECS: | 684-475-5 | | Product Categories: | | | Mol File: | 38227-87-1.mol |  |
| | Lithium tetramethylpiperidide Chemical Properties |
| 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+] |
| 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 | | Storage Class | 4.3 - Hazardous materials which set free flammable gases upon contact with water | | Hazard Classifications | Skin Corr. 1B
Water-react 2 |
| | Lithium tetramethylpiperidide Usage And Synthesis |
| 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 |
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