N,N-Diisopropylethylamine
| Skeletal formula of N,N-diisopropylethylamine | |
| Names | |
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| IUPAC name
Ethyldiisopropylamine
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Other names
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| Identifiers | |
7087-68-5  |
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| ChemSpider | 73565 |
| EC Number | 230-392-0 |
| Jmol 3D model | Interactive image |
| MeSH | N,N-diisopropylethylamine |
| PubChem | 81531 |
| UN number | 2733 |
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| Properties | |
| C8H19N | |
| Molar mass | 129.25 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | Fishy, ammoniacal |
| Density | 0.742 g mL−1 |
| Melting point | −50 to −46 °C (−58 to −51 °F; 223 to 227 K) |
| Boiling point | 126.6 °C; 259.8 °F; 399.7 K |
| Vapor pressure | 4.1 kPa (at 37.70 °C) |
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Refractive index (nD)
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1.414 |
| Vapor pressure | {{{value}}} |
| Related compounds | |
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Related amines
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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. Like 2,2,6,6-tetramethylpiperidine, this compound is a good base but a poor nucleophile, which makes it a useful organic reagent.[1] Hünig's base is named after the German chemist Siegfried Hünig. The compound is a colourless liquid.
Hünig's base is commercially available. It is traditionally prepared by the alkylation of diisopropylamine with diethyl sulfate.[2] If necessary, the compound can be purified by distillation from potassium hydroxide.
Reactions
Non-nucleophilic base
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]
Synthesis of scorpionine
Hünig's base forms a complex heterocyclic compound called scorpionine by a reaction with disulfur dichloride catalyzed by DABCO in a one-pot synthesis.[4]
