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Lithium Diisopropylamide, typ. 25 % solution in Heptane / THF / Ethylbenzene (typ. 1.9 M)

Lithium Diisopropylamide, typ. 28 % solution in Heptane / THF / Ethylbenzene (typ. 2.1 M)

LiC6H14N

CAS Number:  4111-54-0 EC Number:  223-893-0 REACH Number:  01-2119917565-33-0001

Lithium diisopropylamide (often abbreviated LDA, CAS 4111-54-0) is a lithium amide with the molecular formula C₆H₁₄LiN. It is supplied as a typical 28% solution in Heptane, THF & Ethylbenzene.

LDA is commonly used as a strong, non-nucleophilic base for selective deprotonation. It is often used for fast and quantitative enolization of ketones, aldehydes and esters favoring the kinetically controlled product. Furthermore, it can be used for the metalation of arenes.

LDA reacts readily with moisture and air and should be handled under dry, inert conditions. Consult the SDS and site-specific procedures for compatible materials, fire response, and storage.

Physical and Chemical Properties
Property Value
IUPAC Name
lithium di(propan-2-yl)azanide
Molecular Weight
107.13g/mol
Appearance
Liquid
Color
Slight Yellow To Red Brown
Crystallization Temperature
< 0 °C
Flash Point
-21.2 °C 1,013 hPa (Tetrahydrofuran)
Boiling Point
66 °C (Tetrahydrofuran)
Density
ca. 0.80 g/cm3 at 20 °C
Solubility in Water
(Not applicable)

Applications

Strong, low-nucleophilic base for e.g. enolisations.

Specifications

  • LDA (active base) 27 – 29 % (2.1 M)

    Method of Analysis

    Thermometric titration with 2-butanol for the determination of active base. Potentiometric titration of the decomposed product for the determination of total base. Detailed description available on request.

    Handling Instructions

    Lithium Diisopropylamide should be handled under inert gas atmosphere. Avoid contact with eyes, skin and clothes as well as inhalation. Vapors may form explosive mixtures with air. Vapors are heavier than air and may spread along floors. Flash#back possible over considerable distance. Use only explosion-proof equipment. Take measures against electrostatic discharges. Protect from frost, heat and sunlight. Lithium Diisopropylamide decomposes in contact with humidity. In case of fire use dry extinguishers on basis of sodium chloride or limestone powder. Never use water or CO2-extinguishers. Pay also attention to the Safety Data Sheet.

    Storage Instructions

    Lithium Diisopropylamide should be stored in tightly closed containers under exclusion of humidity at gentle temperatures. The product tends to crystallize at temperatures below 0 °C. On prolonged storage at higher temperatures product is decomposing. Average decomposition rate: at 23 °C 0.1 wt.% (of 28 %) per day at 40 °C 0.3 wt.% (of 28 %) per day Recommended storage temperature: 0 - 15 °C. Keep away from heat, sparks and fire. Pay also attention to the Material Safety Data Sheet.

    Legal Disclaimer

    The information presented herein is believed to be accurate and reliable but is presented without guarantee or responsibility on the part of Albemarle Corporation and its subsidiaries and affiliates. It is the responsibility of the user to comply with all applicable laws and regulations and to provide for a safe workplace. The user should consider any health or safety hazards or information contained herein only as a guide and should take those precautions which are necessary or prudent to instruct employees and to develop work practice procedures in order to promote a safe work environment. Further, nothing contained herein shall be taken as an inducement or recommendation to manufacture or use any of the herein materials or processes in violation of existing or future patent.

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