4-Chlorophenylboronic Acid (contains varying amounts of Anhydride)
Catalog Number
ACM1679181-1
CAS
1679-18-1
IUPAC Name
(4-chlorophenyl)boronic acid
Synonyms
4-Chlorobenzeneboronic Acid (contains varying amounts of Anhydride)
Application
4-Chlorophenylboronic Acid (containing varying amounts of Anhydride) is a versatile chemical compound used in a variety of catalytic and coupling reactions. This white or off-white crystalline powder, which exhibits certain solubility in water and high solubility in strong polar organic solvents like dimethyl sulfoxide, serves as an important reactant in numerous processes. Its applications include palladium-catalyzed direct arylation, cyclopalladation, and tandem-type Pd(II)-catalyzed oxidative Heck reactions with intramolecular C-H amidation. Additionally, it is utilized in copper-mediated ligandless aerobic fluoroalkylation, Pd-catalyzed arylative cyclization, and ruthenium catalyzed direct arylation. The compound is effective in ligand-free copper-catalyzed coupling reactions and supports regioselective arylation and alkynylation through Suzuki-Miyaura and Sonogashira cross-coupling reactions. Moreover, it is instrumental in preparing substituted diarylmethylidenefluorenes and Baclofen lactam via Suzuki coupling reactions, and it aids in synthesizing palladium(II) thiocarboxamide complexes as Suzuki coupling catalysts. It is also involved in the formation of biaryls through Suzuki reactions of aryl chlorides, bromides, and iodides with arylboronic acids.
Molecular Weight
156.37
Molecular Formula
C6H6BClO2
Product Information
Canonical SMILES
B(C1=CC=C(C=C1)Cl)(O)O
InChI
InChI=1S/C6H6BClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
InChI Key
CAYQIZIAYYNFCS-UHFFFAOYSA-N
Melting Point
286.5 °C
Appearance
White to Light yellow powder to crystal
Complexity
102
Exact Mass
156.014937g/mol
Hazard Statements
H315 : Causes skin irritation.H319 : Causes serious eye irritation.
Heavy Atom Count
10
MDL Number
MFCD00039137
Monoisotopic Mass
156.014937g/mol
Precautionary Statements
P264 : Wash skin thoroughly after handling.P280 : Wear protective gloves/ eye protection/ face protection.P337 + P313 : If eye irritation persists: Get medical advice/ attention.P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.P332 + P313 : If skin irritation occurs: Get medical advice/ attention.P362 : Take off contaminated clothing and wash before reuse.
Reaxys Registry Number
2936346
Rotatable Bond Count
1
Signal Word
Warning
Solubility In Water
Slightly soluble
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