N,N-Diisopropylethylamine

N,N-Diisopropylethylamine

Chemical name	Ethyldiisopropylamine
Other names	Hunig's base Diisopropylethylamine DIPEA EDIPA
Chemical formula	C₈H₁₉N
Molecular mass	129.25 g/mol
CAS number	[7087-68-5]
Density	0.742 g/cm³
Melting point	< -50 °C
Boiling point	127 °C
SMILES	CC(C)N(CC)C(C)C
Disclaimer and references

N,N-Diisopropylethylamine, or Hünig's base, DIPEA or DIEA, is an organic compound and an amine. It is used in organic chemistry as a base. Because the nitrogen atom is shielded by the two isopropyl groups and an ethyl group only a proton is small enough to easily fit. Just like 2,2,6,6-tetramethylpiperidine, this compound is a good base but a poor nucleophile which makes it a useful organic reagent.

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Hünig's base forms a complex heterocyclic compound called Sscorpionine by a reaction with disulfur dichloride catalyzed by DABCO in a remarkable one-pot synthesis.^[1]

Hünig's base is investigated for its use as a selective reagent in the alkylation of secondary amines to tertiary amines by alkyl halides. This organic reaction is often hampered by a quaternization reaction to the quaternary ammonium salt but this side-reaction is absent when Hünig's base is present.^[2]

References

^ From Hünig's Base to Bis([1,2]dithiolo)-[1,4]thiazines in One Pot: The Fast Route to Highly Sulfurated Heterocycles W. Rees, Carlos F. Marcos,Cecilia Polo, Tomás Torroba,Oleg A. Rakitin Angewandte Chemie International Edition Volume 36, Issue 3 , Pages 281 - 283 2003 Abstract
^ An efficient and operationally convenient general synthesis of tertiary amines by direct alkylation of secondary amines with alkyl halides in the presence of Huenig’s base Jason L. Moore, Stephen M. Taylor, and Vadim A. Soloshonok Arkivoc (EJ-1549C) pp 287-292 2005 Online Article