Lithium diisopropylamide CAS 4111-54-0
Introduction：Basic information about Lithium diisopropylamide CAS 4111-54-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Lithium diisopropylamide Basic information
| 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;Organic-metal salt;Li (Lithium) Compounds;Typical Metal Compounds;4111-54-0 |
| Mol File: | 4111-54-0.mol |
Lithium diisopropylamide Chemical Properties
| Melting point | decomposes [MER06] |
| Boiling point | 65 °C |
| density | 0.864 g/mL at 25 °C (lit.) |
| vapor density | >1 (vs air) |
| Fp | 91 °F |
| storage temp. | 2-8°C |
| solubility | soluble in ethyl ether; insoluble in hydrocarbon solvents |
| form | liquid |
| color | brown |
| Water Solubility | decomposes |
| Sensitive | Air & Moisture Sensitive |
| Merck | 14,3196 |
| BRN | 3655042 |
| InChI | 1S/C6H14N.Li/c1-5(2)7-6(3)4;/h5-6H,1-4H3;/q-1;+1 |
| InChIKey | ZCSHNCUQKCANBX-UHFFFAOYSA-N |
| SMILES | [Li]N(C(C)C)C(C)C |
| CAS DataBase Reference | 4111-54-0(CAS DataBase Reference) |
| EPA Substance Registry System | 2-Propanamine, N-(1-methylethyl)-, lithium salt (4111-54-0) |
Safety Information
| Hazard Codes | C,N,F |
| Risk Statements | 14-17-34-67-65-51/53-35-19-15-11-50/53-14/15-10-40-23/24/25-62-63-37-48/20 |
| Safety Statements | 26-36/37/39-43-45-60-61-62-8-16-23-33-27 |
| RIDADR | UN 3399 4.3/PG 2 |
| WGK Germany | 3 |
| F | 1-10 |
| TSCA | TSCA listed |
| HazardClass | 4.2 |
| PackingGroup | I |
| HS Code | 29211990 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Aquatic Chronic 2 Asp. Tox. 1 Eye Dam. 1 Flam. Liq. 2 Repr. 2 Skin Corr. 1B STOT RE 1 Inhalation STOT SE 3 |
| Chemical Properties | dark yellow to orange or dark red-brown solution. Lithium Diisopropylamide (LDA) [4111-54-0], LiN(CH(CH3)2)2, Mr 107.14 is a whitepyrophoric powder. Freshly prepared, it is soluble in hydrocarbons (in hexane about 10 %), but ittends to precipitate irreversibly from solution as apolymer on heating or prolonged storage. Inethers the solubility is much higher, but with theexception of tetrahydropyran, LDA is decomposed at a rate depending on the ether,concentration, and temperature. |
| Chemical Properties | 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 can be conveniently prepared from butyllithium and diisopropylamine or purchased as a 2 mol/L (25 %) solution in THF and a mixture of various hydrocarbons. Although LDA is unstable in pure THF (at room temperature a 25% solution loses about 1% of its activity per day), the commercially available compositions containing only a limited amount of THF are satisfactory stable for technical applications. |
| Uses | 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. |
| Uses | pH adjuster in colognes and toilet waters. In organic synthesis, particularly, the lithium salt. |
| Uses | Lithium diisopropylamide solution (LDA) can be used:
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| Synthesis | Lithium diisopropylamide has been synthesized by two classical routes. Th 1ost widely adopted route involves in situ formation by deprotonation of diisopropylamineby an alkyllithium reagent, such as butyllithium.Addition of a solutionof butyllithium (in hexane) to a stirred solution of diisopropylamine (freshly distilledfrom CaCl) in tetrahydrofuran directly gives the required solution of lithium diisopropylamide in tetrahydrofuran. This deprotonation process has been reported to be efficient over a wide temperature range (from -78°C to 25°C). The resulting solution of lithium diisopropylamide in tetrahydrofuran appears to be stable, and consequently canbe stored at room temperature for a short period without loss of basicity. Lithium diisopropylamide can also be synthesized directly by addition of lithium todiisopropylamine.This approach gives better quality crystalline lithium diisopropylamide, especially if required for single-crystal X-raystructure determination, than the butyllithium route.The synthesis of lithium diiso-propylamide by in situ deprotonation of diisopropylamine in tetrahydrofuran by analkyllithium reagent is, however, the most commonly used method.Butyllithium isusually the alkyllithium of choice, but otheralkyllithiums have been used (e.g., MeLi) |
| General Description | This material is in a solution of THF/Hexanes (ca. 1:7 ratio, respectively) |
| Flammability and Explosibility | Spontaneously flammable in air (pyrophoric) |
| Purification Methods | It is purified by refluxing over Na wire or NaH for 30minutes and then distilled into a receiver under N2. Because of the low boiling point of the amine, a dispersion of NaH in mineral oil can be used directly in this purification without prior removal of the oil. It is HIGHLY FLAMMABLE, and is decomposed by air and moisture. [Wittig & Hesse Org Synth 50 69 1970, Beilstein 4 H 154, 4 I 369, 4 II 630, 4 III 274, 4 IV 510.] |
Lithium diisopropylamide Preparation Products And Raw materials
| Preparation Products | 3-FURANMETHANOL-->6-FLUORO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBONITRILE-->Ethyl 3-furancarboxylate-->4-METHOXY-1H-PYRROLO[2,3-B]PYRIDINE-2-CARBALDEHYDE-->2-(4-METHOXY-1H-PYRROLO[2,3-B]PYRIDIN-2-YL)ETHANAMINE-->(4-METHOXY-1H-PYRROLO[2,3-B]PYRIDIN-2-YL)METHANOL-->ETHYL 4-METHOXY-1H-PYRROLO[2,3-B]PYRIDINE-2-CARBOXYLATE-->6-FLUORO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBOXYLIC ACID-->5-AMINO-2-METHOXY-ISONICOTINIC ACID-->3-FLUOROQUINOLINE-4-CARBOXYLIC ACID-->3,5-DIFLUOROPYRIDINE-4-CARBALDEHYDE-->2-Chloro-4-iodopyridine-3-carboxaldehyde-->1-(2,6-DIFLUOROPYRIDIN-3-YL)PROPAN-1-ONE-->3-BROMOTHIOPHENE-2-CARBOXAMIDE-->5-FLUORO-2-METHOXYPYRIDINE-4-BORONIC ACID-->1H-Azepine-3-carboxylicacid,hexahydro-,methylester(9CI)-->5-BROMO-2-FLUOROPYRIDINE-3-CARBALDEHYDE-->3-Bromothiophene-2-carbaldehyde-->Rimonabant hydrochloride-->Ethyl 2-oxocyclopentylacetate-->2-Fluoro-3-pyridylboronic acid-->4-ALLYL-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER-->3-Chlorothiophene-2-carboxylic acid-->1-(PHENYLSULFONYL)-1H-INDOLE-2-CARBALDEHYDE-->4-Chloronicotinic acid-->2-Methoxypyridine-3-boronic acid-->3-FLUORO-2-IODOPYRIDINE-4-CARBOXYLIC ACID-->3-BROMOTHIOPHENE-2-CARBONYL CHLORIDE-->3-Chlorothiophene-2-carbonyl chloride |
