| N,N-Diisopropylethylamine | |
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Ethyldiisopropylamine |
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Other names
Hunig's base |
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| Identifiers | |
| CAS number | 7087-68-5 |
| ChemSpider | 73565 |
| Jmol-3D images | Image 1 |
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| 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 |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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. Hünig's base is named after the German chemist Siegfried Hünig.
Contents |
Hünig's base is commercially available. It is traditionally prepared by the reaction of diisopropylamine with diethyl sulfate.[1]
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.[2]
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.[3]