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N,N-Diisopropylethylamine
Hunig.png
IUPAC name
Other names Hunig's base
Diisopropylethylamine
DIPEA
EDIPA
Identifiers
CAS number 7087-68-5 Yes check.svgY
SMILES
Properties
Molecular formula C8H19N
Molar mass 129.25 g/mol
Density 0.742 g/cm3
Melting point

< -50 °C

Boiling point

127 °C, 400 K, 261 °F

Hazards
MSDS External MSDS
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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.

Hunig's base is traditionally prepared by the reaction of diisopropylamine with diethyl sulfate.[1]

Hünig's base forms a complex heterocyclic compound called scorpionine by a reaction with disulfur dichloride catalyzed by DABCO in a remarkable one-pot synthesis.[2]

Hünig's base in Sscorpionine synthesis

Hünig's base was 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.[3]

Hünig's base assists N-alkylations of secondary amines

[edit] References

  1. ^ Hünig, S.; Kiessel, M. (1958). "Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen". Chemische Berichte 91: 380–392. doi:10.1002/cber.19580910223. 
  2. ^ 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
  3. ^ 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



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