Lithium diisopropylamide (LDA) is a white pyrophoric powder. Freshly prepared, it is soluble in hydrocarbons (in hexane about 10 %), but it tends to precipitate irreversibly from solution as a polymer on heating or prolonged storage. In ethers the solubility is much higher, but with the exception of tetrahydropyran, LDA is decomposed at a rate depending on the ether, concentration, and temperature.
Lithium diisopropylamide is a sterically hindered nonnucleophilic strong base used for selective deprotonations, especially for the production of kinetic enolates (i.e., the thermodynamically less favored isomer) and (hetero-)aromatic carbanions. In the production of the serum lipid regulating agent Gemfibrozil one key intermediate is formed by quenching an ester enolate with 1-bromo-3-chloropropane.
Lithium diisopropylamide solution (LDA) can be used:
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Product Name: | Lithium diisopropylamide |
Synonyms: | ithium diisopropyL;LITHIUM DIISOPROPYLAMIDE THF COMPLEX;LITHIUM DIISOPROPYLAMINE;LITHIUM DIISOPROPYLAMIDE;LDA THF COMPLEX;LDA;DIISOPROPYLAMINOLITHIUM;Lithium diisopropylamide solution |
CAS: | 4111-54-0 |
MF: | C6H16LiN |
MW: | 109.14 |
EINECS: | 223-893-0 |
Product Categories: | Classes of Metal Compounds; |
Mol File: | 4111-54-0.mol |
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Lithium diisopropylamide Chemical Properties |
Kiwango myeyuko | decomposes [MER06] |
Kiwango cha kuchemsha | 65 °C |
msongamano | 0.864 g/mL at 25 °C (lit.) |
wiani wa mvuke | >1 (vs air) |
Fp | 91 °F |
joto la kuhifadhi. | 2-8°C |
umumunyifu | soluble in ethyl ether; insoluble in hydrocarbon solvents |
fomu | liquid |
rangi | brown |
Umumunyifu wa Maji | decomposes |
Sensitive | Air & Moisture Sensitive |
Merck | 14,3196 |
BRN | 3655042 |
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