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108-18-9 - Diisopropylamine, 99+% - A10280 - Alfa Aesar

A10280 Diisopropylamine, 99+%

CAS Number
108-18-9
Synonyms

Size Price ($) Quantity Availability
500ml 26.44
2500ml 80.76
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Diisopropylamine, 99+%

MDL
MFCD00008862
EINECS
203-558-5

Chemical Properties

Formula
[(CH3)2CH]2NH
Formula Weight
101.19
Melting point
-61°
Boiling Point
83-84°
Flash Point
-7°(19°F)
Density
0.718
Refractive Index
1.3920
Solubility
Miscible with water.

Applications

Diisopropylamine is used as a precursor to prepare lithium diisopropylamide and sulfenamides, which are used in rubber vulcanization. It is also involved in the synthesis of N,N-Diisopropylethylamine (Hünig's base) obtained by alkylation with diethyl sulfate. Diisopropylammonium bromide is a bromide salt of DIPA used as an inert alternative to barium titanate. It is widely used as solvent as well as an intermediate in the the synthesis of pharmaceuticals, dyes, mineral flotation agents and emulsifiers.

Notes

Air sensitive. Keep container tightly closed in a dry and well-ventilated place. Incompatible with strong acids, strong bases, strong oxidizing agents and plastics.

Literature 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.

Lee, A.; Lundberg, P.; Klinger, D.; Lee, B. F.; Hawker, C. J.; Lynd, N. A. Physiologically relevant, pH-responsive PEG-based block and statistical copolymers with N,N-diisopropylamine units. Polym. Chem. 2013, 4 (24), 5735-5742.

Mei, L.; Peng, H. Y.; Song, S. Y.; Sun, Y. H.; Liu, Q. T.; Zhang, K.; Shi, Y. G. Study on the Nano Material Produced by Diisopropylamine or N Butyl Alcohol as Exchange Solvent. Adv. Mater. Res. 2012, 610-613, 530-533.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H331-H302-H314-H318

Highly flammable liquid and vapour. Toxic if inhaled. Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P210-P260-P261-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,3196
Beilstein
605284
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2921.19
TSCA
Yes
RTECS
IM4025000

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