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512753

Sigma-Aldrich

2-Chloro-6-methoxyphenylboronic acid

≥95%

Synonym(s):

2-Chloro-6-methoxybenzeneboronic acid, 6-Chloro-2-methoxyphenylboronic acid

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About This Item

Linear Formula:
ClC6H3(OCH3)B(OH)2
CAS Number:
385370-80-9
Molecular Weight:
186.40
MDL number:
MFCD04039878
UNSPSC Code:
12352103
PubChem Substance ID:
24873654
NACRES:
NA.22

assay

≥95%

mp

162-165 °C (lit.)

SMILES string

COc1cccc(Cl)c1B(O)O

InChI

1S/C7H8BClO3/c1-12-6-4-2-3-5(9)7(6)8(10)11/h2-4,10-11H,1H3

InChI key

XNWCIDBPLDKKAG-UHFFFAOYSA-N

Application

2-Chloro-6-methoxyphenylboronic acid can be used as a reactant:
  • In the palladium-catalyzed Suzuki-Miyaura coupling reaction.
  • To synthesize canthin-6-one alkaloids by reacting with 8-bromo-1,5-naphthyridin-2-one via Pd-catalyzed Suzuki coupling and Cu-catalyzed amidation reactions.
  • To prepare tryptamines via Suzuki coupling of vinylsulfonylmethyl resin-bound bromotryptamine.

Reactant for:
  • Suzuki coupling
  • Preparation of inhibitors of cholesteryl ester transfer protein to raise HDLc levels
  • Pd-catalyzed Suzuki-Miyaura coupling
  • Solid-phase synthesis of 2,3,5-trisubstituted indoles

Other Notes

Contains varying amounts of anhydride

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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 versatile linkage strategy for solid-phase synthesis of N, N-dimethyltryptamines and β-carbolines
Wu TYH and Schultz PG
Organic Letters, 4(23), 4033-4036 (2002)
Versatile synthesis of functionalised dibenzothiophenes via Suzuki coupling and microwave-assisted ring closure
Rodriguez-Aristegui S, et al.
Organic & Biomolecular Chemistry, 9(17), 6066-6074 (2011)
Two-Step Total Syntheses of Canthin-6-one Alkaloids: New One-Pot Sequential Pd-Catalyzed Suzuki- Miyaura Coupling and Cu-Catalyzed Amidation Reaction
Gollner A and Koutentis PA
Organic Letters, 12(6), 1352-1355 (2010)

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