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480096

Sigma-Aldrich

2,6-Dimethoxyphenylboronic acid

≥97%

Synonym(s):

2,6-Dimethoxybenzeneboronic acid

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About This Item

Linear Formula:
(CH3O)2C6H3B(OH)2
CAS Number:
23112-96-1
Molecular Weight:
181.98
MDL number:
MFCD01318987
UNSPSC Code:
12352103
PubChem Substance ID:
24871546
NACRES:
NA.22

Quality Level

100

Assay

≥97%

mp

110-112 °C (lit.)

SMILES string

COc1cccc(OC)c1B(O)O

InChI

1S/C8H11BO4/c1-12-6-4-3-5-7(13-2)8(6)9(10)11/h3-5,10-11H,1-2H3

InChI key

BKWVXPCYDRURMK-UHFFFAOYSA-N

Application

2,6-Dimethoxyphenylboronic acid can be used as a reagent in:
  • The palladium-catalyzed Suzuki-Miyaura coupling reaction to construct carbon-carbon bond.
  • The synthesis of 2H-imidazo[1,5-a]pyridin-4-ium bromides, which are utilized as precursors for the preparation of N-heterocyclic carbene ligands.
  • The preparation of monosubstituted benzothiazoloquinazolinones as potential monoamine oxidases inhibitors.

Reactant for:
  • Suzuki-Miyaura reactions

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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Imidazo [1, 5-a] pyridine-3-ylidenes-pyridine derived N-heterocyclic carbene ligands
Burstein, C, et al.
Tetrahedron, 61(26), 6207-6217 (2005)
Palladium catalyzed Suzuki-Miyaura coupling with aryl chlorides using a bulky phenanthryl N-heterocyclic carbene ligand
Song C, et al.
Tetrahedron, 61(31), 7438-7446 (2005)
Synthesis of 2-Aryl-12H-benzothiazolo [2, 3-b] quinazolin-12-ones and Their Activity Against Monoamine Oxidases
Jafari B, et al.
ChemistrySelect, 4(37), 11071-11076 (2019)
Ken T Ngo et al.
Journal of the American Chemical Society, 139(7), 2604-2618 (2017-01-25)
Electrocatalytic reduction of CO

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