Diisopropylamine
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| Names | |
|---|---|
| IUPAC name
N-Isopropylpropan-2-amine
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| Other names
N-(1-Methylethyl)-2-propanamine
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| Identifiers | |
108-18-9  |
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| Abbreviations | DIPA |
| 605284 | |
| ChemSpider | 7624 |
| EC Number | 203-558-5 |
| Jmol 3D model | Interactive image |
| PubChem | 7912 |
| RTECS number | IM4025000 |
| UNII | BR9JLI40NO |
| UN number | 1158 |
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| Properties | |
| C6H15N | |
| Molar mass | 101.19 g·mol−1 |
| Appearance | Colorless liquid |
| Odor | Fishy, ammoniacal |
| Density | 0.722 g mL−1 |
| Melting point | −61.00 °C; −77.80 °F; 212.15 K |
| Boiling point | 83 to 85 °C; 181 to 185 °F; 356 to 358 K |
| miscible[1] | |
| Vapor pressure | 6.7 kPa (at 20 °C) |
| Acidity (pKa) | 11.07 (in water) at 25 deg C |
| Basicity (pKb) | 3.43[2] |
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Refractive index (nD)
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1.392–1.393 |
| Thermochemistry | |
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Std enthalpy of
formation (ΔfH |
−173.6–−168.4 kJ mol−1 |
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Std enthalpy of
combustion (ΔcH |
−4.3363–−4.3313 MJ mol−1 |
| 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 | |
Diisopropylamine is a secondary amine with the chemical formula (CH3)2HC-NH-CH(CH3)2. It is best known as its lithium derivative of its conjugate base, lithium diisopropylamide, known as "LDA". LDA is a strong, non-nucleophilic base.
Diisopropylamine can be dried by distillation from potassium hydroxide (KOH) or drying over sodium wire.[3]
Reactions and uses
Diisopropylamine is primarily used as a precursor to two herbicides, diallate and triallate, as well as certain sulfenamides used in the vulcanization of rubber.[4] It is also used to prepare N,N-Diisopropylethylamine (Hünig's base) by alkylation with diethyl sulfate.[5]
The bromide salt of diisopropylamine, diisopropylammonium bromide, is an organic molecular solid whose crystals are ferroelectric at room temperature.[6] This renders it a possible more biospherically inert alternative to barium titanate.
Preparation
Diisopropylamine is commercially available. It may be prepared by the reductive amination of acetone with ammonia using a modified copper oxide, generally copper chromite, as a catalyst:[7][8]
- NH
3 + 2(CH
3)
2CO + 2H
2 → C
6H
15N + 2H
2O
References
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- ↑ Armarego, W. L. F. and Perrin, D. D. Purification of Laboratory Chemicals 4th Ed. pg 186, Butterworth and Heinemann: Boston, 1996.
- ↑ Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_001
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- ↑ US 2686811, Willard Bull, "One-step process for preparing diisopropylamine"
