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Lithium diisopropylamide

Basic information Safety Supplier Related

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:
C6H14LiN
MW:
107.12306
EINECS:
223-893-0
Product Categories:
  • Classes of Metal Compounds
  • Organic-metal salt
  • Li (Lithium) Compounds
  • Typical Metal Compounds
Mol File:
4111-54-0.mol
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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)
Flash point:
91 °F
storage temp. 
2-8°C
form 
liquid
color 
brown
Water Solubility 
decomposes
Sensitive 
Air & Moisture Sensitive
Merck 
14,3196
BRN 
3655042
CAS DataBase Reference
4111-54-0(CAS DataBase Reference)
EPA Substance Registry System
2-Propanamine, N-(1-methylethyl)-, lithium salt (4111-54-0)
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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
1-10
TSCA 
Yes
HazardClass 
4.2
PackingGroup 
I
HS Code 
29211990

MSDS

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Lithium diisopropylamide Usage And Synthesis

Chemical Properties

dark yellow to orange or dark red-brown solution

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.

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 diisopropylamideSupplier

Chengdu Hongsheng Sci-Tech Development Co..,Ltd Gold
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028-37690186-
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Sichuan Weibo Science and Technology Co., Ltd. Gold
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+86 (28) 8757-8473 / +86 13880582998
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Lianyungang Yilong Chemical Co., Ltd. Gold
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Energy Chemical Gold
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021-58432009
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sales8178@energy-chemical.com