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374733

Sigma-Aldrich

2,6-Diisopropylaniline

97%

Synonyme(s) :

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

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About This Item

Formule linéaire :
[(CH3)2CH]2C6H3NH2
Numéro CAS:
24544-04-5
Poids moléculaire :
177.29
Beilstein:
2208763
Numéro CE :
246-305-4
Numéro MDL:
MFCD00008887
Code UNSPSC :
12352100
ID de substance PubChem :
24863333
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Pression de vapeur

<0.01 mmHg ( 20 °C)

Niveau de qualité

200

Essai

97%

Forme

liquid

Indice de réfraction

n20/D 1.532 (lit.)

pb

257 °C (lit.)

Pf

−45 °C (lit.)

Densité

0.94 g/mL at 25 °C (lit.)

Chaîne SMILES 

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

Clé InChI

WKBALTUBRZPIPZ-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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.[1]

2,6-Diisopropylaniline is an important organic intermediate widely used to synthesize plastics and dyes.[2]
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).[3]

[3]2,6-Diisopropylaniline is an important organic intermediate widely used to synthesize plastics and dyes.[2]

Application

2,6-Diisopropylaniline may be used in the preparation of multitopic Schiff-base ligand precursors.[4] 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.[5] It may be used to prepare N-heterocyclic carbene complexes for α-arylation of acyclic ketones,[6] amination of haloarenes,[6] and aqueous Suzuki coupling.[1]
2,6-Diisopropylaniline may be used in the preparation of organocatalyst based on naphthalene diimides (NDIs).[7]

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H319,H412

Conseils de prudence

P273 - P305 + P351 + P338

Classification des risques

Aquatic Chronic 3 - Eye Irrit. 2

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 2

Équipement de protection individuelle

Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
MKCT3060
MKCT3058
MKCT3059
MKCT6096
MKCR1036

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

Sigma-Aldrich

574074

1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride

2,6-Diéthylaniline 98%

Sigma-Aldrich

149381

2,6-Diéthylaniline

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.
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)
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)
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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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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