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Diisopropylamine

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Not to be confused with Diisopropanolamine.
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
CAS Number
3D model (JSmol)
Beilstein Reference 605284
ChemSpider
ECHA InfoCard 100.003.235 Edit this at Wikidata
EC Number
  • 203-558-5
PubChem CID
RTECS number
  • IM4025000
UNII
UN number 1158
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H15N/c1-5(2)7-6(3)4/h5-7H,1-4H3Key: UAOMVDZJSHZZME-UHFFFAOYSA-N
SMILES
  • CC(C)NC(C)C
Properties
Chemical formula C6H15N
Molar mass 101.193 g·mol
Appearance Colorless liquid
Odor Fishy, ammoniacal
Density 0.722 g mL
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
Solubility in water miscible
Vapor pressure 9.3 kPa (at 20°C)
Acidity (pKa) 11.07 (in water) (conjugate acid)
Basicity (pKb) 3.43
Refractive index (nD) 1.392–1.393
Thermochemistry
Std enthalpy of
formation (ΔfH298) 		−173.6 to −168.4 kJ mol
Std enthalpy of
combustion (ΔcH298) 		−4.3363 to −4.3313 MJ mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark
Signal word Danger
Hazard statements H225, H302, H314, H332
Precautionary statements 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)
Autoignition
temperature 		315 °C (599 °F; 588 K)
Explosive limits 1.1–7.1%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 770 mg kg (oral, rat)
  • >10 g kg (dermal, rabbit)
LC50 (median concentration) 1140 ppm (rat, 2 hr)
1000 ppm (mouse, 2 hr)
LCLo (lowest published) 2207 ppm (rabbit, 2.5 hr)
2207 ppm (guinea pig, 80 min)
2207 ppm (cat, 72 min)
NIOSH (US health exposure limits):
PEL (Permissible) TWA 5 ppm (20 mg/m)
REL (Recommended) TWA 5 ppm (20 mg/m)
IDLH (Immediate danger) 200 ppm
Related compounds
Related amines
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

Diisopropylamine is a common amine nucleophile in organic synthesis. Because it is bulky, it is a more selective nucleophile than other similar amines, such as dimethylamine.

It reacts with organolithium reagents to give lithium diisopropylamide (LDA). LDA is a strong, non-nucleophilic base

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.

It is also used to prepare N,N-diisopropylethylamine (Hünig's base) by alkylation with diethyl sulfate.

The bromide salt of diisopropylamine, diisopropylammonium bromide, is a room-temperature organic ferroelectric material.

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:

NH3 + 2 (CH3)2CO + 2 H2 → C6H15N + 2 H2O

Diisopropylamine can be dried by distillation from potassium hydroxide (KOH) or drying over sodium wire.

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

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0217". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ CID 7912 from PubChem
  3. ^ "Diisopropylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. John E. McMurry, Jack Melton (1977). "Conversion of Nitro to Carbonyl by Ozonolysis of Nitronates: 2,5-Heptanedione". Organic Syntheses. 56: 36. doi:10.15227/orgsyn.056.0036.
  5. Denmark, Scott; Ryabchuk, Pavel; Min Chi, Hyung; Matviitsuk, Anastassia (2019). "Preparation of a Diisopropylselenophosphoramide Catalyst and its Use in Enantioselective Sulfenoetherification". Organic Syntheses. 96: 400–417. doi:10.15227/orgsyn.096.0400. PMC 8439352. PMID 34526731.
  6. George M. Rubottom, John M. Gruber, Henrik D. Juve, Jr, , Dan A. Charleson (1986). "α-Hydroxy Ketones from the Oxidation of Enol Silyl Ethers with m-Chloroperbenzoic Acid: 6-Hydroxy- 3,5,5-trimethyl-2-cyclohexen-1-one". Organic Syntheses. 64: 118. doi:10.15227/orgsyn.064.0118.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (15 June 2000). Amines, Aliphatic. Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3527303854. OL 9052422M. {{cite encyclopedia}}: |journal= ignored (help)
  8. Hünig, Siegfried; Kiessel, Max (1 April 1958). "Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen" [Specific proton acceptors as auxiliary bases in alkylation and dehydrohalogenation reactions]. Chemische Berichte (in German). 91 (2). Wiley-VCH: 380–392. doi:10.1002/cber.19580910223. ISSN 0009-2940. OCLC 889715844.
  9. Fu, Da-Wei; Cai, Hong-Ling; Liu, Yuanming; Ye, Qiong; Zhang, Wen; et al. (25 January 2013). "Diisopropylammonium Bromide Is a High-Temperature Molecular Ferroelectric Crystal". Science. 339 (6118): 425–428. Bibcode:2013Sci...339..425F. doi:10.1126/science.1229675. eISSN 1095-9203. ISSN 0036-8075. LCCN 17024346. OCLC 1644869. PMID 23349285. S2CID 12389978.
  10. Löffler, Karl (1 April 1910). "Über eine neue Bildungsweise primärer und sekundärer Amine aus Ketonen" [About a new way of forming primary and secondary amines from ketones]. Berichte der Deutschen Chemischen Gesellschaft (in German). 43 (2): 2031–2035. doi:10.1002/cber.191004302145. ISSN 0365-9496. OCLC 219854722.
  11. US 2686811, Willard Bull, "One-step process for preparing diisopropylamine" 
  12. Armarego, W. L. F.; Perrin, D. D. (16 October 1996). Purification of Laboratory Chemicals (4th ed.). Butterworth-Heinemann. ISBN 978-0750628396. LCCN 97109714. OCLC 762966259. OL 722457M.
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