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Diisopropylamine
Diisopropylamine
Diisopropylamine
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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).
☒N verify (what is checkY☒N ?)

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.

Reactions and use

[edit]

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

[edit]

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

[edit]

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

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Diisopropylamine

View on Grokipedia
from Grokipedia
Diisopropylamine is a secondary aliphatic with the molecular formula C₆H₁₅N and the systematic name N-(1-methylethyl)propan-2-amine, existing as a clear, colorless with a strong ammonia-like odor at . This compound, with a molecular weight of 101.19 g/mol, has a of 84 °C, a of -61 °C, and a of 0.717 g/cm³ at 20 °C, making it less dense than and soluble in it (110 g/L at 25 °C) while highly soluble in organic solvents such as , , and . Diisopropylamine is widely employed as a non-nucleophilic in , particularly for generating (LDA) by with at low temperatures, which serves as a potent for formation and other reactions in . It also functions as a key intermediate in the manufacture of herbicides like diallate and triallate, as well as pharmaceuticals and pesticides, and finds applications as a , stabilizer for compounds such as , and an ingredient in . Due to its flammability (flash point of -13 °C) and corrosivity, diisopropylamine poses hazards including severe and eye irritation, damage upon , and potential if swallowed or absorbed, necessitating proper ventilation, protective , and storage away from oxidizers and acids during handling.

Properties

Physical properties

Diisopropylamine has the molecular formula C6H15N and a molecular weight of 101.19 g/mol. It is a colorless to pale yellow liquid with a fishy, amine-like odor. The compound has a of 84.1 °C (191.4 °F) at standard pressure. Its melting point is -61 °C (-78 °F). The density is 0.718 g/cm³ at 25 °C, rendering it less dense than . Diisopropylamine is slightly soluble in (10 g/L), miscible with and , with a of 70 mmHg at 20 °C. It exhibits a of -7 °C (20 °F), signifying high flammability. Additional properties include an of 316 °C (601 °F) and a of 1.391 at 20 °C.

Chemical properties

Diisopropylamine has the molecular formula C₆H₁₅N and the (CH₃)₂CHNHCH(CH₃)₂, featuring a central atom bonded to two isopropyl groups and one . This configuration classifies it as a secondary aliphatic , characterized by the bearing two alkyl substituents and one hydrogen. The pKₐ of its conjugate acid is 11.07 (in at 25 °C), reflecting moderate basicity typical of such amines, where the on is available for but influenced by inductive effects from the alkyl groups. As a secondary , diisopropylamine exhibits key reactivity as both a and a base. It forms salts with acids via of the , as shown in the equation: (iPr)2NH+H+→(iPr)2NH2+(i\text{Pr})_2\text{NH} + \text{H}^+ \rightarrow (i\text{Pr})_2\text{NH}_2^+ (where iPr denotes the isopropyl group). This protonated form predominates in acidic environments, rendering the compound soluble in aqueous media. Additionally, it undergoes N-alkylation with alkyl halides through or with acid chlorides or anhydrides to yield tertiary amines or amides, respectively, under controlled conditions. The presence of two bulky isopropyl groups imparts significant steric hindrance around the nitrogen atom, which reduces its nucleophilicity compared to primary amines by impeding access to electrophiles. This hindrance limits over-alkylation and enhances the compound's stability relative to less substituted amines, particularly in reactions requiring selective basicity without excessive nucleophilic side reactions.

Production

Laboratory preparation

Diisopropylamine can be prepared in the laboratory through of acetone with in the presence of gas and a catalyst such as or . This process involves the condensation of the primary amine with the ketone to form an intermediate, followed by catalytic to yield the secondary amine. Conditions typically involve moderate temperatures (140–200°C) and pressures (500–1500 psi) in a sealed vessel, with water added to facilitate the reaction. Similar procedures using and excess acetone have been reported to produce diisopropylamine in up to 67% yield based on the amine starting material, with used to isolate the product from monoisopropylamine byproducts. An alternative laboratory route involves the base-catalyzed of with . The reaction proceeds via , where the primary attacks the alkyl to form the secondary , with a base such as or excess used to neutralize the byproduct: (CH3)2CHNH2+(CH3)2CHCl→base(CH3)2CHNHCH(CH3)2+HCl\text{(CH}_3\text{)}_2\text{CHNH}_2 + \text{(CH}_3\text{)}_2\text{CHCl} \xrightarrow{\text{base}} \text{(CH}_3\text{)}_2\text{CHNHCH(CH}_3\text{)}_2 + \text{HCl}
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