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)

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 

Yes

HazardClass 

4.2

PackingGroup 

I

HS Code 

29211990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

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 diisopropylamide(4111-54-0)Related Product Information

• Isopropylamine
• Lithium diisopropylamide mono(tetrahydrofuran)
• Lithium diisopropylamide mono(tetrahydrofuran) complex solution
• LITHIUM DIETHYLAMIDE
• LITHIUM TETRAMETHYLPIPERIDIDE
• LITHIUM DICYCLOHEXYLAMIDE
• LITHIUM DIMETHYLAMIDE
• Lithium diisopropylamide
• 1-Methyl-2-pyrrolidinone
• N,N'-Diisopropylcarbodiimide
• Lithium chloride
• Lithium
• Diisopropylamine
• Lithium amide
• N,N-Diisopropylethylamine
• Lithium oxide
• Lithium bis(trimethylsilyl)amide
• DIISOPROPYL ZINC 1.0M SOLUTION IN TOLU&