Diisopropylamine
From Wikipedia, the free encyclopedia
| Diisopropylamine | |
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N-Isopropylpropan-2-amine[citation needed] |
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| Identifiers | |
| Abbreviations | DIPA[citation needed] |
| CAS number | 108-18-9  |
| PubChem | 7912 |
| ChemSpider | 7624 |
| UNII | BR9JLI40NO |
| EC number | 203-558-5 |
| UN number | 1158 |
| RTECS number | IM4025000 |
| Beilstein Reference | 605284 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C6H15N |
| Molar mass | 101.19 g mol−1 |
| Exact mass | 101.120449485 g mol−1 |
| Appearance | Colorless, transparent liquid |
| Density | 0.722 g mL−1 |
| Melting point |
-96 °C, 176.85 K, -141 °F |
| Boiling point |
83-85 °C, 356-358 K, 181-185 °F |
| Vapor pressure | 6.7 kPa (at 20 °C) |
| Acidity (pKa) | 40 |
| Basicity (pKb) | 54 |
| Refractive index (nD) | 1.392 |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
−173.6–−168.4 kJ mol−1 |
| Std enthalpy of combustion ΔcH |
−4.3363–−4.3313 MJ mol−1 |
| Hazards | |
| GHS pictograms |    |
| GHS signal word | DANGER |
| GHS hazard statements | H225, H302, H314, H332 |
| GHS precautionary statements | P210, P280, P305+351+338, P310 |
| EU Index | 612-129-00-5 |
| EU classification |  F  C |
| R-phrases | R11, R20/22, R34 |
| S-phrases | (S1/2), S16, S26, S36/37/39 |
| NFPA 704 |
 3
2
0
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| Flash point | −17 °C |
| Autoignition temperature |
315 °C |
| Explosive limits | 1.1–8.5% |
| LD50 |
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| Related compounds | |
| Related alkanylamines | |
 (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 | |
Diisopropylamine is a secondary amine with the chemical formula (CH3)2HC-NH-CH(CH3)2. It is best known as its lithium salt, lithium diisopropylamide, known as "LDA". LDA is a strong, non-nucleophilic base.
Diisopropylamine can be dried by distillation over potassium hydroxide (KOH) or drying over sodium wire or sodium hydride (NaH) followed by distillation under N2 into a dry receiver.[1]
Diisopropylamine is also used for the synthesis of diisopropylethylamine (Hünig's base), by reaction with diethyl sulfate. [2]
[edit] References
- ^ Armarego, W. L. F. and Perrin, D. D. Purification of Laboratory Chemicals 4th Ed. pg 186, Butterworth and Heinemann: Boston, 1996.
- ^ Hünig, S.; Kiessel, M. (1958). "Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen". Chemische Berichte 91 (2): 380–392. doi:10.1002/cber.19580910223.
