N,N-DIISOPROPYLETHYLAMINE

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| Chemical name
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| Other names
| Hunig's base
Diisopropylethylamine
DIPEA
EDIPA
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| Chemical formula
| C₈H₁₉N
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| Molecular mass
| g/mol
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| CAS number
| []
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| Density
| g/cm³
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| Melting point
| °C
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| Boiling point
| °C
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| SMILES
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'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.
Hünig's base forms a complex heterocyclic compound called Sscorpionine by a reaction with dichloro disulfide 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]

Contents

References

External links

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

External links

★ MSDS for Hunig's base

★ Company named after Hünig's base [1]

★ Sscorpionine homepage [2]