Diisopropylamine

Diisopropylamine
IUPAC name

N-Isopropylpropan-2-amine
Other names

DIPA
Identifiers
CAS number 108-18-9 Y
ChemSpider 7624 Y
UNII BR9JLI40NO Y
Jmol-3D images Image 1
Properties
Molecular formula C6H15N
Molar mass 101.19 g mol−1
Appearance Colorless liquid
Density 0.717 g/mL liquid
Melting point

-61 °C, 212 K, -78 °F
Boiling point

84 °C, 357 K, 183 °F
Acidity (pKa) 40
Hazards
MSDS External MSDS
R-phrases R11 R20/21/22
S-phrases S26 S36
Main hazards Harmful
NFPA 704
3
2
0
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Diisopropylamine is a secondary amine with the chemical formula (CH3)2HC-NH-CH(CH3)2. It is best known as its lithium salt, lithium diisopropylamide, known as "LDA". LDA is a strong, non-nucleophilic base.

Diisopropylamine can be dried by distillation over potassium hydroxide (KOH) or drying over sodium wire or sodium hydride (NaH) followed by distillation under N2 into a dry receiver.[1]

Diisopropylamine is also used for the synthesis of diisopropylethylamine (Hünig's base), by reaction with diethyl sulfate. [2]

References

  1. ^ Armarego, W. L. F. and Perrin, D. D. Purification of Laboratory Chemicals 4th Ed. pg 186, Butterworth and Heinemann: Boston, 1996.
  2. ^ Hünig, S.; Kiessel, M. (1958). "Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen". Chemische Berichte 91 (2): 380–392. doi:10.1002/cber.19580910223.