512753
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:
Molecular Weight:
186.40
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Assay
≥95%
mp
162-165 °C (lit.)
functional group
chloro
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.[1][2]
- 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.[2]
- To prepare tryptamines via Suzuki coupling of vinylsulfonylmethyl resin-bound bromotryptamine.[3]
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
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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)
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)
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)
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