Diisopropylamine

• Catalog No.: A10280
• CAS Number: 108-18-9
• M. F.: C6H15N
• M. W.: 101.19
• Purity: 99+%

SYNONYMS

• Title: 二异丙胺
• IUPAC name: bis(propan-2-yl)amine
• IUPAC Traditional name: diisopropylamine

DATABASE IDS

• MDL Number: MFCD00008862
• Beilstein Number: 605284
• CAS Number: 108-18-9
• EC Number: 203-558-5
• Merck Index: 143196

PROPERTIES

• Purity: 99+%
• Boiling Point: 83-84°C
• Density: 0.718
• Flash Point: -7°C(19°F)
• Melting Point: -61°C
• Refractive Index: 1.3920
• GHS Hazard statements: H225-H314-H318-H302-H332
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• European Hazard Symbols: Flammable (F)
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 11-20/22-34
• RTECS: IM4025000
• Safety Statements: 16-26-36/37/39-45
• TSCA Listed: 是
• Hazard Class: 3
• UN Number: UN1158
• Packing Group: II

REFERENCES

• Precursor of the sterically-hindered strong base lithium diisopropylamide (LDA), which has a greater "kinetic-basicity" than some thermodynamically stronger bases, e.g. alkyllithiums, and therefore finds wide application in lithiation reactions. LDA is a particularly useful base for the preparation of carboxylic acid dianions and ester enolates. For a review, see: Synthesis, 521 (1982).
• LDA is generally prepared in situ by reaction of diisopropylamine with an alkyllithium; numerous examples in Org. Synth. Coll., 6, 7, 8, 9, and subsequent annual volumes. For discussion of methods for preparation, including Li metal in the presence of an aromatic hydrocarbon as electron-acceptor, see: Synthesis, 463 (1979); see also (Li in ether): Liebigs Ann. Chem., 1471 (1980).
• LDA cleaves 1,3-dithiolanes (ethylene dithioacetals) to the carbonyl compounds: Synthesis, 1087 (1982):
  
• 1,3-Dithianes are not cleaved under these conditions.