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374733

Sigma-Aldrich

2,6-Diisopropylaniline

97%

Sinonimo/i:

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

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5 G
CHF 71.40
25 G
CHF 253.00

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5 G
CHF 71.40
25 G
CHF 253.00

About This Item

Formula condensata:
[(CH3)2CH]2C6H3NH2
Numero CAS:
24544-04-5
Peso molecolare:
177.29
Beilstein:
2208763
Numero CE:
246-305-4
Numero MDL:
MFCD00008887
Codice UNSPSC:
12352100
ID PubChem:
24863333
NACRES:
NA.22

CHF 71.40

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Tensione di vapore

<0.01 mmHg ( 20 °C)

Saggio

97%

Stato

liquid

Indice di rifrazione

n20/D 1.532 (lit.)

P. ebollizione

257 °C (lit.)

Punto di fusione

−45 °C (lit.)

Densità

0.94 g/mL at 25 °C (lit.)

Stringa SMILE

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
WKBALTUBRZPIPZ-UHFFFAOYSA-N

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Descrizione generale

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]

Applicazioni

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]

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H319,H412

Consigli di prudenza

P273 - P305 + P351 + P338

Classi di pericolo

Aquatic Chronic 3 - Eye Irrit. 2

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 2

Dispositivi di protezione individuale

Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
MKCT3059
MKCT3060
MKCT3058
MKCT6096
MKCR1036

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2,6-Diethylaniline 98%

Sigma-Aldrich

149381

2,6-Diethylaniline

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)
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)
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. 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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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    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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