Diisopropylamine Explained

Diisopropylamine should not be confused with Diisopropanolamine.

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.^[1] Because it is bulky, it is a more selective nucleophile than other similar amines, such as dimethylamine.^[2]

It reacts with organolithium reagents to give lithium diisopropylamide (LDA). LDA is a strong, non-nucleophilic base^[3]

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.^[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 a room-temperature organic ferroelectric material.^[6]

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:^{[7] [8]}

Diisopropylamine can be dried by distillation from potassium hydroxide or drying over sodium wire.^[9]

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.

Notes and References

1. 10.15227/orgsyn.056.0036. Conversion of Nitro to Carbonyl by Ozonolysis of Nitronates: 2,5-Heptanedione. Organic Syntheses. 1977. 56. 36. John E. McMurry, Jack Melton.
2. 34526731. 10.15227/orgsyn.096.0400. Preparation of a Diisopropylselenophosphoramide Catalyst and its Use in Enantioselective Sulfenoetherification. 2019. Denmark. Scott. Pavel. Ryabchuk. Hyung . Min Chi . Anastassia. Matviitsuk. Organic Syntheses. 96. 400–417. 8439352. free.
3. 10.15227/orgsyn.064.0118. α-Hydroxy Ketones from the Oxidation of Enol Silyl Ethers with m-Chloroperbenzoic Acid: 6-Hydroxy- 3,5,5-trimethyl-2-cyclohexen-1-one. George M. Rubottom, John M. Gruber, Henrik D. Juve, Jr,, Dan A. Charleson. Organic Syntheses. 1986. 64. 118.
4. Encyclopedia: Karsten . Eller . Erhard . Henkes . Roland . Rossbacher . Hartmut . Höke . Amines, Aliphatic . Ullmann's Encyclopedia of Industrial Chemistry . 2000-06-15 . . 978-3527303854 . OL9052422M . 10.1002/14356007.a02_001 . dmy-all.
5. Hünig . Siegfried . Kiessel . Max . 1958-04-01 . Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen . Specific proton acceptors as auxiliary bases in alkylation and dehydrohalogenation reactions . de . . . 91 . 2 . 380392 . 10.1002/cber.19580910223 . 0009-2940 . 889715844 . dmy-all.
6. Fu . Da-Wei . Cai . Hong-Ling . Liu . Yuanming . Ye . Qiong . Zhang . Wen . Zhang . Yi . Chen . Xue-Yuan . Giovannetti . Gianluca . Capone . Massimo . Li . Jiangyu . Xiong . Ren-Gen . 5 . 2013-01-25 . Diisopropylammonium Bromide Is a High-Temperature Molecular Ferroelectric Crystal . . en . 339 . 6118 . 425428 . 10.1126/science.1229675 . 23349285 . 2013Sci...339..425F . 12389978 . 0036-8075 . 1095-9203 . 17024346 . 1644869 . dmy-all.
7. . 43 . 2 . 2031–2035 . 10.1002/cber.191004302145 . Über eine neue Bildungsweise primärer und sekundärer Amine aus Ketonen . About a new way of forming primary and secondary amines from ketones . de . Karl . Löffler. 1910-04-01 . 0365-9496 . 219854722 . dmy-all .
8. Willard Bull . One-step process for preparing diisopropylamine. US . 2686811.
9. Book: Armarego . W. L. F. . Perrin . D. D. . Purification of Laboratory Chemicals . 4th . . 1996-10-16 . 978-0750628396 . 762966259 . OL722457M . 97109714 . dmy-all.