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
SMILES N(C(C)C)C(C)C
InChI InChI=1S/C6H15N/c1-5(2)7-6(3)4/h5-7H,1-4H3 Y Key: UAOMVDZJSHZZME-UHFFFAOYSA-N Y InChI=1/C6H15N/c1-5(2)7-6(3)4/h5-7H,1-4H3 Key: UAOMVDZJSHZZME-UHFFFAOYAA
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
Y (verify) (what is: Y/N?) 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.