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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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Santos-Filho, E. F.; et al.
Tetrahedron Letters, 52, 5288-5288 (2011)
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
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
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)
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
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