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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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
SHBJ8473
SHBD7179V
16329AH
17006HB
15130JS

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Mueller Hinton Agar suitable for microbiology, NutriSelect® Plus

Millipore

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Mueller Hinton Agar

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)
Imidazo [1, 5-a] pyridine-3-ylidenes-pyridine derived N-heterocyclic carbene ligands
Burstein, C, et al.
Tetrahedron, 61(26), 6207-6217 (2005)
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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