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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

Quality Level

100

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

480118-VAR:
480118-BULK:
480118-25G:
480118-5G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS6492
MKCQ1873
MKCF7124
MKBX8820V
MKBS4054V

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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)
Highly efficient synthesis of buflavine: a unique Amaryllidaceae alkaloid
Sahakitpichan P and Ruchirawat S
Tetrahedron Letters, 44(28), 5239-5241 (2003)
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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