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Diisopropylamine is a secondary amine with the chemical formula (Me2CH)2NH (Me = methyl). Diisopropylamine is a colorless liquid with an ammonia-like odor. Its lithium derivative, lithium diisopropylamide, known as LDA is a widely used reagent.
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| Names | |
|---|---|
| Preferred IUPAC name
N-(Propan-2-yl)propan-2-amine | |
| Other names
Di(propan-2-yl)amine N-Isopropylpropan-2-amine (Diisopropyl)amine (The name diisopropylamine is deprecated.) | |
| Identifiers | |
3D model (JSmol) |
|
| 605284 | |
| ChemSpider | |
| ECHA InfoCard | 100.003.235 |
| EC Number |
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PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 1158 |
CompTox Dashboard (EPA) |
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| |
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| Properties | |
| C6H15N | |
| Molar mass | 101.193 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 | 9.3 kPa (at 20°C)[2] |
| Acidity (pKa) | 11.07 (in water) (conjugate acid) |
| Basicity (pKb) | 3.43[2] |
Refractive index (nD) |
1.392–1.393 |
| Thermochemistry | |
Std enthalpy of formation (ΔfH⦵298) |
−173.6 to −168.4 kJ mol−1 |
Std enthalpy of combustion (ΔcH⦵298) |
−4.3363 to −4.3313 MJ mol−1 |
| Hazards | |
| GHS labelling: | |
   | |
| Danger | |
| H225, H302, H314, H332 | |
| P210, P280, P305+P351+P338, P310 | |
| NFPA 704 (fire diamond) | |
| Flash point | −17 °C (1 °F; 256 K) |
| 315 °C (599 °F; 588 K) | |
| Explosive limits | 1.1–7.1%[1] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
|
LC50 (median concentration) |
1140 ppm (rat, 2 hr) 1000 ppm (mouse, 2 hr)[3] |
LCLo (lowest published) |
2207 ppm (rabbit, 2.5 hr) 2207 ppm (guinea pig, 80 min) 2207 ppm (cat, 72 min)[3] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) |
TWA 5 ppm (20 mg/m3) [skin][1] |
REL (Recommended) |
TWA 5 ppm (20 mg/m3) [skin][1] |
IDLH (Immediate danger) |
200 ppm[1] |
| Related compounds | |
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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Diisopropylamine is a common amine nucleophile in organic synthesis.[4] Because it is bulky, it is a more selective nucleophile than other similar amines, such as dimethylamine.[5]
It reacts with organolithium reagents to give lithium diisopropylamide (LDA). LDA is a strong, non-nucleophilic base[6]
The main commercial applications of diisopropylamine is as a precursor to the herbicide, diallate and triallate as well as certain sulfenamides used in the vulcanization of rubber.[7]
It is also used to prepare N,N-diisopropylethylamine (Hünig's base) by alkylation with diethyl sulfate.[8]
The bromide salt of diisopropylamine, diisopropylammonium bromide, is a room-temperature organic ferroelectric material.[9]
Diisopropylamine, which is commercially available, may be prepared by the reductive amination of acetone with ammonia using a modified copper oxide, generally copper chromite, as a catalyst:[10][11]
- NH3 + 2 (CH3)2CO + 2 H2 → C6H15N + 2 H2O
Diisopropylamine can be dried by distillation from potassium hydroxide (KOH) or drying over sodium wire.[12]: 186
Diisopropylamine causes burns by all exposure routes. Inhalation of high concentrations of its vapor may cause symptoms like headache, dizziness, tiredness, nausea and vomiting.
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