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480118

Sigma-Aldrich

3,4-Dimethoxyphenylboronic acid

≥95.0%

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About This Item

Linear Formula:
(CH3O)2C6H3B(OH)2
CAS Number:
122775-35-3
Molecular Weight:
181.98
MDL number:
MFCD01074574
UNSPSC Code:
12352103
PubChem Substance ID:
24871548
NACRES:
NA.22

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

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)

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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)

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