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480061 Sigma-Aldrich

2,6-Dimethylphenylboronic acid

≥95.0%

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

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Properties

Related Categories Aryl Boronic Acids, Boronic Acids, Boronic Acids and Derivatives, Chemical Synthesis, Disubstituted Aryl Boronic Acids,
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

Description

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

Packaging

5, 25 g in glass bottle

Other Notes

contains varying amounts of anhydride

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Arylboronic Acids

We are pleased to present its complete selection of arylboronic acids, the building blocks of the Suzuki coupling experiment. Most arylboronic acids readily undergo dehydration reactions to give a cy...
ChemFiles 2001, 1.1, 5.
Keywords: Building blocks, Coupling reactions, Dehydration reaction, Suzuki coupling

Boronic Acids - ChemFiles 2007

Most boronic acids readily undergo dehydration reactions to give a cyclic (trimer) anhydride. Our selection of boronic acids may contain varying amounts of this cyclic anhydride. Fortunately, the aci...
ChemFiles 2007, 7.7, 3.
Keywords: Coupling reactions, Dehydration reaction, Suzuki coupling

Peer-Reviewed Papers
15

References

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