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N,N-diisopropylethylamine
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{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin-left:1em; background: #ffffff;"
! colspan="2" align=center bgcolor="#ccccff" | '''N,N-diisopropylethylamine'''
|-
|
IUPAC nomenclature Chemical name
| N,N-diisopropylethylamine
|-
|
Chemical formula
| C
8H
19N
|-
|
Molecular mass
| 129.25 g/mol
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|
Melting point
|
|-
|
Boiling point
| 127 °C
|-
|
Density
| 0.742 g/cm
3
|-
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CAS registry number CAS number
| 7087-68-5
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|
Simplified molecular input line entry specification SMILES
|
|-
| colspan="2" align="center" |
Image:Diisopropylethylamine.gif
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| colspan=2 align=center style="background: #ccccff;"|
wikipedia:Chemical infobox Disclaimer and references
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'''N,N-Diisopropylethylamine''' or '''Hünig's base''' is an
organic compound and an
amine. It is used in
organic chemistry as a
base (chemistry) base. Because the
nitrogen atom is shielded by the two
isopropyl groups and an
ethyl group only a
hydrogen ion proton is small enough to fit. Just like
2,2,6,6-tetramethylpiperidine this compound is a base but not a
nucleophile which makes it a special 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 #references 1.
Image:Sscorpionine.gif Hünig's base in Sscorpionine synthesis
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
#references 2.
Image:Hunigsbaseaminereaction.gif Hünig's base assists N-alkylations of secondary amines
External links
*
MSDS http://physchem.ox.ac.uk [http://physchem.ox.ac.uk/MSDS/DI/N,N-diisopropylethylamine.html]
* Company named after Hünig's base [http://www.hunigs.com/hunigs.htm]
* Sscorpionine homepage [http://www.chm.bris.ac.uk/motm/sscorpionine/sscorpionine.htm]
References
*
#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''' [http://www3.interscience.wiley.com/cgi-bin/abstract/106591858/ABSTRACT Abstract]
*
#references 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''' [http://www.arkat-usa.org/ark/journal/2005/I06_Juaristi/1549/EJ-1549C.asp Online Article]
category:amines
category:bases
de:Diisopropylethylamin
see
N,N-Diisopropylethylamine
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