Diisopropylamine

Diisopropylamine
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
108-18-9 YesY
3D model (Jmol) Interactive image
Abbreviations DIPA
605284
ChemSpider 7624 YesY
ECHA InfoCard 100.003.235
EC Number 203-558-5
PubChem 7912
RTECS number IM4025000
UNII BR9JLI40NO YesY
UN number 1158
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) (conjugate acid)
Basicity (pKb) 3.43[2]
1.392–1.393
Thermochemistry
−173.6 to −168.4 kJ mol−1
−4.3363 to −4.3313 MJ mol−1
Hazards
GHS pictograms
GHS signal word DANGER
H225, H302, H314, H332
P210, P280, P305+351+338, P310
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]
Lethal dose or concentration (LD, LC):
  • 770 mg kg−1 (oral, rat)
  • >10 g kg−1 (dermal, rabbit)
1140 ppm (rat, 2 hr)
1000 ppm (mouse, 2 hr)[3]
2207 ppm (rabbit, 2.5 hr)
2207 ppm (guinea pig, 80 min)
2207 ppm (cat, 72 min)[3]
US health exposure limits (NIOSH):
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
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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.[4]

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.[5] It is also used to prepare N,N-Diisopropylethylamine (Hünig's base) by alkylation with diethyl sulfate.[6]

The bromide salt of diisopropylamine, diisopropylammonium bromide, is an organic molecular solid whose crystals are ferroelectric at room temperature.[7] 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:[8][9]

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

References

  1. 1 2 3 4 5 "NIOSH Pocket Guide to Chemical Hazards #0217". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ "DIISOPROPYLAMINE". pub chem. NIH. Retrieved 20 October 2015.
  3. 1 2 "Diisopropylamine". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ Armarego, W. L. F. and Perrin, D. D. Purification of Laboratory Chemicals 4th Ed. pg 186, Butterworth and Heinemann: Boston, 1996.
  5. ↑ 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
  6. ↑ Hünig, S.; Kiessel, M. (1958). "Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen". Chemische Berichte. 91 (2): 380–392. doi:10.1002/cber.19580910223.
  7. ↑ "An organic alternative to oxides? Organic ferroelectric molecule shows promise for memory chips, sensors". phys.org. Jan 24, 2013.
  8. ↑ Karl Löffler. "Über eine neue Bildungsweise primärer und sekundärer Amine aus Ketonen". Berichte. 43 (2): 2031–2035. doi:10.1002/cber.191004302145.
  9. ↑ US 2686811, Willard Bull, "One-step process for preparing diisopropylamine"
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