374733

2,6-Diisopropylaniline

97%

• Synonym(s): 2,6-Bis(1-methylethyl)benzenamine, 2,6-Bis(propan-2-yl)aniline, 2,6-Diisopropylphenylamine
• Linear Formula: [(CH₃)₂CH]₂C₆H₃NH₂
• CAS Number: 24544-04-5
• Molecular Weight: 177.29
• Beilstein: 2208763
• EC Number: 246-305-4
• MDL number: MFCD00008887
• UNSPSC Code: 12352100
• PubChem Substance ID: 24863333
• NACRES: NA.22

Properties

• vapor pressure: <0.01 mmHg ( 20 °C)
• Assay: 97%
• form: liquid
• 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 important organic intermediate widely used to synthesize plastics and dyes.

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).

2,6-Diisopropylaniline is an important organic intermediate widely used to synthesize plastics and dyes.

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).

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H319,H412
• Precautionary Statements: P273 - P305 + P351 + P338
• Hazard Classifications: Aquatic Chronic 3 - Eye Irrit. 2
• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 2
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves