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374733 Sigma-Aldrich

2,6-Diisopropylaniline

97%

  • CAS Number 24544-04-5

  • Linear Formula [(CH3)2CH]2C6H3NH2

  • Molecular Weight 177.29

  •  Beilstein/REAXYS Number 2208763

  •  EC Number 246-305-4

  •  MDL number MFCD00008887

  •  PubChem Substance ID 24863333

  •  NACRES NA.22

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Properties

Related Categories Amines, Building Blocks, C12, Chemical Synthesis, Nitrogen Compounds - Organic Building Blocks,
vapor pressure   <0.01 mmHg ( 20 °C)
assay   97%
refractive index   n20/D 1.532 (lit.)
bp   257 °C (lit.)
mp   −45 °C (lit.)
density   0.94 g/mL at 25 °C (lit.)
SMILES string   CC(C)c1cccc(C(C)C)c1N
InChI   1S/C12H19N/c1-8(2)10-6-5-7-11(9(3)4)12(10)13/h5-9H,13H2,1-4H3
InChI key   WKBALTUBRZPIPZ-UHFFFAOYSA-N

Description

General description

2,6-Diisopropylaniline is an amine. It undergoes condensation with triacetylmethane in toluene in the presence of p-toluenesulfonic acid provides 3-[1-(2,6-diisopropylphenylamino)ethylidene]pentane-2,4-dione.

2,6-Diisopropylaniline is an aromatic amine. It reacts with bis(trimethylsilylmethyl)yttrium complexes supported by bulky amidopyridinate (Ap) and amidinate (Amd) ligands to afford yttrium alkyl anilido species. This reaction involves the elimination of TMS (Trimethylsilane).

Application

2,6-Diisopropylaniline may be used in the preparation of multitopic Schiff-base ligand precursors. It may be used in the preparation of NSN-donor proligand, 4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene. It may be used to prepare N-heterocyclic carbene complexes for α-arylation of acyclic ketones, amination of haloarenes, and aqueous Suzuki coupling.

2,6-Diisopropylaniline may be used in the preparation of organocatalyst based on naphthalene diimides (NDIs).

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
2
RTECS 
BX4025000
Flash Point(F) 
242.6 °F
Flash Point(C) 
117 °C

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Protocols & Articles
Peer-Reviewed Papers
15

References

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