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374733

Sigma-Aldrich

2,6-Diisopropylaniline

97%

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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:
Molecular Weight:
177.29
Beilstein/REAXYS Number:
2208763
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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

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1 of 4

This Item
574074157716147389
2,6-Diisopropylaniline 97%

374733

2,6-Diisopropylaniline

2,6-Diisopropylaniline technical grade, 90%

157716

2,6-Diisopropylaniline

Triacetylmethane 97%

147389

Triacetylmethane

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

form

liquid

form

solid

form

liquid

form

liquid

refractive index

n20/D 1.532 (lit.)

refractive index

-

refractive index

n20/D 1.532 (lit.)

refractive index

n20/D 1.487 (lit.)

bp

257 °C (lit.)

bp

-

bp

257 °C (lit.)

bp

203.5 °C (lit.)

mp

−45 °C (lit.)

mp

278 °C (dec.) (lit.)

mp

−45 °C (lit.)

mp

-

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).

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

ppe

Eyeshields, Gloves


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Customers Also Viewed

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1 of 2

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.
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)
Characterization and performance of Pd-La/spinel catalyst for preparation of 2, 6-diisopropylaniline
Ruixia J, et al.
Applied Catalysis A: General, 250(2), 209-220 (2003)
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
Reactions of Bis (alkyl) yttrium Complexes Supported by Bulky N, N Ligands with 2, 6-Diisopropylaniline and Phenylacetylene.
Karpov AV, et al.
Organometallics, 31(15), 5349-5357 (2012)

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