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480061

Sigma-Aldrich

2,6-Dimethylphenylborsäure

≥95.0%

Synonym(e):

2,6-Dimethylbenzeneboronic acid, 2,6-Xyleneboronic acid, 2,6-Xylylboronic acid

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About This Item

Lineare Formel:
(CH3)2C6H3B(OH)2
CAS-Nummer:
100379-00-8
Molekulargewicht:
149.98
MDL-Nummer:
MFCD01009693
UNSPSC-Code:
12352103
PubChem Substanz-ID:
24871544
NACRES:
NA.22

Qualitätsniveau

100

Assay

≥95.0%

Verunreinigungen

<10% water

mp (Schmelzpunkt)

105 °C (dec.) (lit.)

SMILES String

Cc1cccc(C)c1B(O)O

InChI

1S/C8H11BO2/c1-6-4-3-5-7(2)8(6)9(10)11/h3-5,10-11H,1-2H3

InChIKey

ZXDTWWZIHJEZOG-UHFFFAOYSA-N

Verwandte Kategorien

Anwendung

Reagent used for
  • Palladium catalyzed Suzuki-Miyaura coupling reactions
  • One-pot ipso-nitration of arylboronic acids including broader substrate scope of heterocycles and functional groups
  • Nickel-Catalyzed Cross-Coupling of Chromene Acetals and Boronic Acids
  • Visible-light initiated aerobic oxidative hydroxylation catalyzed by Ru-complex
  • Rhodium(I)-catalyzed 1,4-addition reactions
  • Pd-catalyzed homocouplings
  • Expanded scope of Cu assisted Suzuki-Miyaura coupling reactions including aryl chlorides and polyhalo aryl boronates

Reagent used in Prepration of
  • Orally bioavialable G Protein-Coupled Receptor 40 agonists for diabetes treatment
  • Solid phase synthesis and antitumor structure-activity relationship of Smac triazoloprolines and biarylalanines tetrapeptide libraries
  • Protein Kinase inhibitors

Sonstige Hinweise

contains varying amounts of anhydride

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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Room-temperature synthesis of tetra-ortho-substituted biaryls by NHC-catalyzed Suzuki-Miyaura couplings.
Linglin Wu et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(46), 12886-12890 (2011-10-11)
Laura A T Cleghorn et al.
ChemMedChem, 6(12), 2214-2224 (2011-09-14)
New drugs are urgently needed for the treatment of tropical parasitic diseases such as leishmaniasis and human African trypanosomiasis (HAT). This work involved a high-throughput screen of a focussed kinase set of ~3400 compounds to identify potent and parasite-selective inhibitors
Expanding the scope of the Cu assisted Suzuki-Miyaura reaction
Crowley, B. M.; et al.
Tetrahedron Letters, 52, 5055-5059 (2011)
Satoshi Mikami et al.
Journal of medicinal chemistry, 55(8), 3756-3776 (2012-03-21)
As part of a program to identify potent GPR40 agonists with drug-like properties suitable for clinical development, the incorporation of polar substituents was explored with the intention of decreasing the lipophilicity of our recently disclosed phenylpropanoic acid derivative 1. This
Thomas J A Graham et al.
Organic letters, 14(6), 1616-1619 (2012-03-06)
A modular and highly efficient protocol for the synthesis of 2-aryl- and heteroaryl-2H-chromenes is described. Under base-free conditions, readily accessible 2-ethoxy-2H-chromenes undergo C(sp(3))-O activation and C(sp(3))-C bond formation in the presence of an inexpensive nickel catalyst and boronic acids. This
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