Diisopropylamine

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Diisopropylamine
Skeletal formula of diisopropylamine
Names
IUPAC name
N-Isopropylpropan-2-amine
Other names
N-(1-Methylethyl)-2-propanamine
Identifiers
108-18-9 YesY
Abbreviations DIPA
605284
ChemSpider 7624 YesY
EC Number 203-558-5
Jmol 3D model Interactive image
PubChem 7912
RTECS number IM4025000
UNII BR9JLI40NO YesY
UN number 1158
  • InChI=1S/C6H15N/c1-5(2)7-6(3)4/h5-7H,1-4H3 YesY
    Key: UAOMVDZJSHZZME-UHFFFAOYSA-N YesY
  • CC(C)NC(C)C
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) at 25 deg C
Basicity (pKb) 3.43[2]
1.392–1.393
Thermochemistry
−173.6–−168.4 kJ mol−1
−4.3363–−4.3313 MJ mol−1
Vapor pressure {{{value}}}
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.[3]

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

The bromide salt of diisopropylamine, diisopropylammonium bromide, is an organic molecular solid whose crystals are ferroelectric at room temperature.[6] 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:[7][8]

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

References

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  3. Armarego, W. L. F. and Perrin, D. D. Purification of Laboratory Chemicals 4th Ed. pg 186, Butterworth and Heinemann: Boston, 1996.
  4. 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
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  8. US 2686811, Willard Bull, "One-step process for preparing diisopropylamine"