| Identification | More | [Name]
Lithium diisopropylamide | [CAS]
4111-54-0 | [Synonyms]
DIISOPROPYLAMINOLITHIUM
LDA
LDA THF COMPLEX
LITHIUM DIISOPROPYLAMIDE
LITHIUM DIISOPROPYLAMIDE THF COMPLEX
LITHIUM DIISOPROPYLAMINE
2-Propanamine,N-(1-methylethyl)-,lithiumsalt
n-(1-methylethyl)-2-propanaminlithiumsalt
Lithium diisopropylamide solution
Lithium dlisopropylamide
LITHIUM DIISOPROPYLAMIDE, 10 WT. % SOLUT ION IN MINERAL OIL
LITHIUM DIISOPROPYLAMIDE, 2.0M SOLUTION IN HEPTANE/THF/ETHYLBENZENE
LITHIUM DIISOPROPYLAMIDE, 1.8M SOLUTION IN THF/HEPTANE/ETHYLBENZENE
LITHIUM DIISOPROPYLAMIDE, 10 WT. % SUSPE NSION IN HEXANES
Lithium diisopropylamide solution, ~2 M in THF/heptane/ethylbenzene
LITHIUM DIISOPROPYLAMIDE, 2M SOLUTION IN THF/HEPTANE
Lithium diisopropylamide, 2M solution in THF/n-heptane/ethylbenzene
LITHIUMDIISOPROPYLAMIDE,2MSOLUTIONINTETRAHYDROFURAN/HEPTANE/ETHYLBENZENE
lithium diisopropylamide (LDA)
LITHIUM DIISOPROPYLAMIDE, 2M SOLUTION IN THF/N-HEPTANE | [EINECS(EC#)]
223-893-0 | [Molecular Formula]
C6H14LiN | [MDL Number]
MFCD00064449 | [Molecular Weight]
107.12 | [MOL File]
4111-54-0.mol |
| Chemical Properties | Back Directory | [Appearance]
dark yellow to orange or dark red-brown solution | [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 | [Detection Methods]
T | [Merck ]
3196 | [BRN ]
3655042 | [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. | [CAS DataBase Reference]
4111-54-0(CAS DataBase Reference) | [Storage Precautions]
Air sensitive;Store under nitrogen;Moisture sensitive | [EPA Substance Registry System]
4111-54-0(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
dark yellow to orange or dark red-brown solution | [Uses]
pH adjuster in colognes and toilet waters. In organic synthesis, particularly, the lithium salt. | [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) | [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.] | [General Description]
This material is in a solution of THF/Hexanes (ca. 1:7 ratio, respectively) | [Flammability and Explosibility]
Spontaneouslyflammableinair(pyrophoric) |
| Safety Data | Back Directory | [Hazard Codes ]
C,N,F | [Risk Statements ]
R14:Reacts violently with water.
R17:Spontaneously flammable in air.
R34:Causes burns.
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R35:Causes severe burns.
R19:May form explosive peroxides.
R15:Contact with water liberates extremely flammable gases.
R11:Highly Flammable.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R14/15:Reacts violently with water, liberating extremely flammable gases .
R10:Flammable.
R40:Limited evidence of a carcinogenic effect.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S8:Keep container dry .
S16:Keep away from sources of ignition-No smoking .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S33:Take precautionary measures against static discharges .
S27:Take off immediately all contaminated clothing . | [RIDADR ]
UN 3399 4.3/PG 2
| [WGK Germany ]
3
| [F ]
1-10 | [TSCA ]
Yes | [HazardClass ]
4.2 | [PackingGroup ]
I | [HS Code ]
29211990 |
| Raw materials And Preparation Products | Back Directory | [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 |
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