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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 Code

13 - Non 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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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)
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)

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