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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.

Additional recommended knowledge

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

  1. ^ 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
  2. ^ 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
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "N,N-Diisopropylethylamine". A list of authors is available in Wikipedia.
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