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483486

Sigma-Aldrich

2,4-Dimethoxyphenylboronic acid

95%

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About This Item

Linear Formula:
(CH3O)2C6H3B(OH)2
CAS Number:
133730-34-4
Molecular Weight:
181.98
MDL number:
MFCD01074590
UNSPSC Code:
12352103
PubChem Substance ID:
24871896
NACRES:
NA.22

Assay

95%

mp

125-127 °C (lit.)

SMILES string

COc1ccc(B(O)O)c(OC)c1

InChI

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

InChI key

SQTUYFKNCCBFRR-UHFFFAOYSA-N

Application

2,4-Dimethoxyphenylboronic acid can be used:
  • As a reactant in meatal-catalyzed Suzuki−Miyaura cross-coupling reaction.
  • To prepare hydroxy(trimethoxy)phenanthrene by cross-coupling with bromo(benzyloxy)methoxybenzaldehyde followed by condensation and debenzylation reaction.
  • To synthesize 2,4-dimethoxy-1-(trifluoromethyl)benzene via Cu-catalyzed trifluoromethylation reaction.

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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Synthesis of Phenanthrenes and Polycyclic Heteroarenes by Transition-Metal Catalyzed Cycloisomerization Reactions
Mamane V, et al.
Chemistry?A European Journal , 10(18), 4556-4575 (2004)
Suzuki-Miyaura cross-coupling of α-phosphoryloxy enol ethers with arylboronic acids
Pedzisa L, et al.
Tetrahedron Letters, 49(26), 4142-4144 (2008)
Copper-catalyzed trifluoromethylation of aryl-and vinylboronic acids with generation of CF3-radicals
Li, Yang, et al.
Chemical Communications (Cambridge, England), 49(26), 2628-2630 (2013)

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