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Sigma-Aldrich

2,6-Diisopropylanilin

97%

Synonym(e):

2,6-Bis(1-methylethyl)benzenamine, 2,6-Bis(propan-2-yl)aniline, 2,6-Diisopropylphenylamine

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About This Item

Lineare Formel:
[(CH3)2CH]2C6H3NH2
CAS-Nummer:
24544-04-5
Molekulargewicht:
177.29
Beilstein:
2208763
EG-Nummer:
246-305-4
MDL-Nummer:
MFCD00008887
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24863333
NACRES:
NA.22

Dampfdruck

<0.01 mmHg ( 20 °C)

Assay

97%

Form

liquid

Brechungsindex

n20/D 1.532 (lit.)

bp

257 °C (lit.)

mp (Schmelzpunkt)

−45 °C (lit.)

Dichte

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

InChIKey

WKBALTUBRZPIPZ-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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).

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H319,H412

Gefahreneinstufungen

Aquatic Chronic 3 - Eye Irrit. 2

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 2

Persönliche Schutzausrüstung

Eyeshields, Gloves

Analysenzertifikate (COA)

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1,3-Bis-(2,6-diisopropylphenyl)-imidazoliumchlorid 97%

Sigma-Aldrich

574074

1,3-Bis-(2,6-diisopropylphenyl)-imidazoliumchlorid

2,6-Diethylanilin 98%

Sigma-Aldrich

149381

2,6-Diethylanilin

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)
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
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)
Balamurugan Vidjayacoumar et al.
Dalton transactions (Cambridge, England : 2003), 41(26), 8175-8189 (2012-05-09)
A rigid NSN-donor proligand, 4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene (H(2)[TXA(2)], 1) was prepared by palladium-catalyzed coupling of 2,6-diisopropylaniline with 4,5-dibromo-2,7-di-tert-butyl-9,9-dimethylthioxanthene. Deprotonation of 1 using (n)BuLi provided Li(2)(DME)(2)[TXA(2)] (2), and subsequent reaction with UCl(4) afforded [Li(DME)(3)][(TXA(2))UCl(3)] (4). The analogous NON-donor ligated complex [(XA(2))UCl(3)K(DME)(3)] [3; XA(2)
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