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480118

Sigma-Aldrich

3,4-Dimethoxyphenylboronic acid

≥95.0%

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

Quality Level

Assay

≥95.0%

mp

245-250 °C (lit.)

SMILES string

COc1ccc(cc1OC)B(O)O

InChI

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

InChI key

RCVDPBFUMYUKPB-UHFFFAOYSA-N

Application

3,4-Dimethoxyphenylboronic acid can be used:
  • As a substrate in the cross-coupling reaction with 5,7-dichloropyrido[4,3-d]pyrimidine catalyzed by palladium.
  • As a starting material for the synthesis of buflavine 1, a natural alkaloid.
  • In one of the key synthetic steps for the preparation of lipidated malarial glycosylphosphatidylinositols (GPI) disaccharide.
  • To prepare 3,3″,4,4″-tetramethoxy-1,1′:4′,1″-terphenyl by reacting with 1,4-dibromobenzene using Pd catalyst.

Other Notes

Contains varying amounts of anhydride

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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A Suzuki-Miyaura coupling mediated deprotection as key to the synthesis of a fully lipidated malarial GPI disaccharide
Liu X and Seeberger PH
Chemical Communications (Cambridge, England), 15, 1708-1709 (2004)
3, 3″, 4, 4″-Tetramethoxy-1, 1′: 4′, 1″-terphenyl
Pui L, et al.
Acta Crystallographica Section E, Structure Reports Online, 67(Pt 8), o1892-o1892 (2011)
Regioselective cross-coupling reactions and nucleophilic aromatic substitutions on a 5, 7-dichloropyrido [4, 3-d] pyrimidine scaffold
Jang M, et al.
Tetrahedron Letters, 47(50), 8917-8920 (2006)

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