Diisopropylamine, 99+%, Thermo Scientific Chemicals

Name: Diisopropylamine, 99+%, Thermo Scientific Chemicals
SKU: A10280.0F

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Catalog number A10280.0F

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2500 mL

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Chemical Identifiers

CAS108-18-9

IUPAC Namebis(propan-2-yl)amine

Molecular FormulaC6H15N

InChI KeyUAOMVDZJSHZZME-UHFFFAOYSA-N

SMILESCC(C)NC(C)C

Specifications

Specification Sheet

FormLiquid

Appearance (Color)Clear colorless

Identification (FTIR)Conforms (non-U.S. specification)

Refractive Index1.3905-1.3935 @ 20°C (non-U.S. specification)

Assay (GC)≥99.0%

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

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.

Solubility
Miscible with water.

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.

RUO – Research Use Only

General 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.