Diisopropylamine

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
Diisopropylamine
Skeletal formula of diisopropylamine
Skeletal formula of 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
3D model (JSmol)
605284
ChemSpider
ECHA InfoCard 100.003.235 Edit this at Wikidata
EC Number
  • 203-558-5
RTECS number
  • IM4025000
UNII
UN number 1158
  • InChI=1S/C6H15N/c1-5(2)7-6(3)4/h5-7H,1-4H3 checkY
    Key: UAOMVDZJSHZZME-UHFFFAOYSA-N checkY
  • CC(C)NC(C)C
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]
1.392–1.393
Thermochemistry
−173.6 to −168.4 kJ mol−1
−4.3363 to −4.3313 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark
Danger
H225, H302, H314, H332
P210, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
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]
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
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reactions and use

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]

Preparation

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 

Toxicity

Diisopropylamine causes burns by all exposure routes. Inhalation of high concentrations of its vapor may cause symptoms like headache, dizziness, tiredness, nausea and vomiting.

References

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