Diisopropylamine

Diisopropylamine
Names
IUPAC name
N-Isopropylpropan-2-amine
Other names
N-(1-Methylethyl)-2-propanamine
Identifiers
Abbreviations DIPA
605284
108-18-9 Yes
ChemSpider 7624 Yes
EC number 203-558-5
Jmol-3D images Image
PubChem 7912
RTECS number IM4025000
UNII BR9JLI40NO Yes
UN number 1158
Properties
Molecular formula
 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 °C; 181 °F; 356 K
miscible[1]
Vapor pressure 6.7 kPa (at 20 °C)
Acidity (pKa) 40
Basicity (pKb) 54
1.392–1.393
Thermochemistry
Std enthalpy of
formation (ΔfHo298)
 −173.6–−168.4 kJ mol−1
Std enthalpy of
combustion (ΔcHo298)
 −4.3363–−4.3313 MJ mol−1
Hazards
GHS pictograms
GHS signal word DANGER
H225, H302, H314, H332
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
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
3
2
0
Flash point −17 °C (1 °F; 256 K)
315 °C (599 °F; 588 K)
Explosive limits 1.1–7.1%[1]
  • 770 mg kg−1 (oral, rat)
  • >10 g kg−1 (dermal, rabbit)
US health exposure limits (NIOSH):
TWA 5 ppm (20 mg/m3) [skin][1]
TWA 5 ppm (20 mg/m3) [skin][1]
200 ppm[1]
Related compounds
Related amines
Related compounds
Except where noted otherwise, data is 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.[2]

Reactions and uses

Diisopropylamine is primarily used as a precursor to two herbicides, dilate and triallate, as well as certain sulfenamides used in the vulcanization of rubber.[3] It is also used to prepare N,N-Diisopropylethylamine (Hünig's base) by alkylation with diethyl sulfate.[4]

The bromide salt of diisopropylamine, diisopropylammonium bromide, is an organic molecular solid whose crystals are ferroelectric at room temperature.[5] 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:[6][7]

NH
3 + 2(CH
3)
2CO + 2H
2 → C
6H
15N + 2H
2O

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 "NIOSH Pocket Guide to Chemical Hazards #0217". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ Armarego, W. L. F. and Perrin, D. D. Purification of Laboratory Chemicals 4th Ed. pg 186, Butterworth and Heinemann: Boston, 1996.
  3. ↑ 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
  4. ↑ Hünig, S.; Kiessel, M. (1958). "Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen". Chemische Berichte 91 (2): 380–392. doi:10.1002/cber.19580910223.
  5. ↑ "An organic alternative to oxides? Organic ferroelectric molecule shows promise for memory chips, sensors". phys.org. Jan 24, 2013.
  6. ↑ Karl Löffler. "Über eine neue Bildungsweise primärer und sekundärer Amine aus Ketonen". Berichte 43 (2): 2031–2035. doi:10.1002/cber.191004302145.
  7. ↑ US 2686811, Willard Bull, "One-step process for preparing diisopropylamine"