Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

480061

Sigma-Aldrich

2,6-Dimethylphenylboronic acid

≥95.0%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

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

Quality Level

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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

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)
Sebastian T Le Quement et al.
ACS combinatorial science, 13(6), 667-675 (2011-09-13)
Apoptotic induction mechanisms are of crucial importance for the general homeostasis of multicellular organisms. In cancer the apoptotic pathways are downregulated, which, at least partly, is due to an abundance of inhibitors of apoptosis proteins (IAPs) that block the apoptotic
Santos-Filho, E. F.; et al.
Tetrahedron Letters, 52, 5288-5288 (2011)
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
Rhodium(I)-catalyzed 1,4-addition of arylboronic acids to acrylic acid in water: one-step preparation of 3-arylpropionic acids
Vautravers, N. R.; Breit, B.
Synlett, 17, 2517-2520 (2011)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service