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480061

Sigma-Aldrich

2,6-Dimethylphenylboronic acid

≥95.0%

Synonym(s):

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

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About This Item

Linear Formula:
(CH3)2C6H3B(OH)2
CAS Number:
100379-00-8
Molecular Weight:
149.98
MDL number:
MFCD01009693
UNSPSC Code:
12352103
PubChem Substance ID:
24871544
NACRES:
NA.22

Quality Level

100

Assay

≥95.0%

impurities

<10% water

mp

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

InChI key

ZXDTWWZIHJEZOG-UHFFFAOYSA-N

Related Categories

Application

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

Other Notes

contains varying amounts of anhydride

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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