Diisopropylamine

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Diisopropylamine
Skeletal formula of diisopropylamine
Identifiers
Abbreviations DIPA
CAS number 108-18-9 YesY
PubChem 7912
ChemSpider 7624 YesY
UNII BR9JLI40NO YesY
EC number 203-558-5
UN number 1158
RTECS number IM4025000
Beilstein Reference 605284
Jmol-3D images Image 1
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 to 85 °C; 181 to 185 °F; 356 to 358 K
Vapor pressure 6.7 kPa (at 20 °C)
Acidity (pKa) 40
Basicity (pKb) 54
Refractive index (nD) 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 The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
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 Highly Flammable F Corrosive 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
Flash point −17 °C (1 °F; 256 K)
Explosive limits 1.1–8.5%
LD50
  • 770 mg kg−1 (oral, rat)
  • >10 g kg−1 (dermal, rabbit)
Related compounds
Related amines
Related compounds
Except where noted otherwise, 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.[1]

Reactions and uses[edit]

Diisopropylamine is primarily used as a precursor to two herbicides, dialate and trialate, as well as certain sulfenamides used in the vulcanization of rubber.[2] It is also used to prepare N,N-Diisopropylethylamine (Hünig's base) by alkylation with diethyl sulfate.[3]

The bromide salt of diisopropylamine, diisopropylammonium bromide, is an organic molecular solid whose crystals are ferroelectric at room temperature.[4] This renders it a possible more biospherically inert alternative to barium titanate.

Preparation[edit]

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:[5][6]

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

References[edit]

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