374733
2,6-Diisopropylaniline
97%
Synonym(s):
2,6-Bis(1-methylethyl)benzenamine, 2,6-Bis(propan-2-yl)aniline, 2,6-Diisopropylphenylamine
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About This Item
Linear Formula:
[(CH3)2CH]2C6H3NH2
CAS Number:
Molecular Weight:
177.29
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
246-305-4
Beilstein/REAXYS Number:
2208763
MDL number:
Assay:
97%
Form:
liquid
vapor pressure
<0.01 mmHg ( 20 °C)
Quality Level
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
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 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.
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 organocatalyst based on naphthalene diimides (NDIs).
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.
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signalword
Warning
hcodes
Hazard Classifications
Aquatic Chronic 3 - Eye Irrit. 2
Storage Class
10 - Combustible liquids
wgk
WGK 2
ppe
Eyeshields, Gloves
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Electron-deficient naphthalene diimides as efficient planar Π-acid organocatalysts for selective oxidative C-C coupling of 2, 6-di-tert-butylphenol: A temperature effect.
Ke H, et al.
J. Mol. Catal. A: Chem., 385, 26-30 (2014)
Christoph Fleckenstein et al.
Chemical communications (Cambridge, England), (27), 2870-2872 (2007-07-05)
Sulfonated, water-soluble imidazolium and imidazolinium salts were synthesized and the respective Pd-complexes with N,N'-bis(2,6-dialkyl-4-SO(3)(-)-phenyl)imidazol-2-ylidene and N,N'-bis(2,6-dialkyl-4-SO(3)(-)-phenyl)-4,5-dihydroimidazol-2-ylidene ligands were applied in aqueous Suzuki coupling reactions of aryl chlorides.
Kouki Matsubara et al.
The Journal of organic chemistry, 72(14), 5069-5076 (2007-06-15)
Arylation of both acyclic ketones and primary and secondary amines was achieved using a new, simple, stable, and easy-to-access nickel(II)-halide complex bearing mixed PPh3/N-heterocyclic carbene ligands as a catalyst precursor. Acyclic ketones were first arylated at the alpha-position with the
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 374733-25G | 04061831834758 |
| 374733-5G | 04061836820367 |