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523976 Sigma-Aldrich

4-Hydroxyphenylboronic acid

≥95.0%

Synonym: (p-Hydroxyphenyl)boronic acid, 4-Hydroxybenzeneboronic acid, p-hydroxy-benzeneboronic acid

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Properties

Related Categories Aryl Boronic Acids, Boronic Acids, Boronic Acids and Derivatives, Chemical Synthesis, Monosubstituted Aryl Boronic Acids,
Quality Level   100
assay   ≥95.0%
mp   >230 °C (lit.)
SMILES string   OB(O)c1ccc(O)cc1
InChI   1S/C6H7BO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8-10H
InChI key   COIQUVGFTILYGA-UHFFFAOYSA-N

Description

Application

Reagent used for
• Suzuki-Miyaura coupling and Stille coupling and potential for introducing different alkyl groups
• Palladium-catalyzed aminocarbonylation and cross-coupling reactions
• Bio-supported palladium nanoparticles as phosphine-free catalyst for Suzuki reaction in water
• Cu2O-catalyzed aerobic oxidative cross-coupling of tetrazoles

Reagent used in Preparation of
• PDK1 inhibitory activity (cancer cell growth, survival, and tumorigenesis inhibitor)
• Rod-like dendronized polymers contg. G4 and G5 ester dendrons via macromonomer approach by living ROMP
• Estrone-derived cyclopamine analogs as Sonic Hedgehog signaling inhibitors for anti-cancer chemotherapeutics
• Enzymatic inhibitors for the treatment of gram-negative bacterial infections

Packaging

1, 5 g in glass bottle

Other Notes

Contains varying amounts of anhydride

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Boronic Acids - ChemFiles 2007

Most boronic acids readily undergo dehydration reactions to give a cyclic (trimer) anhydride. Our selection of boronic acids may contain varying amounts of this cyclic anhydride. Fortunately, the aci...
ChemFiles 2007, 7.7, 3.
Keywords: Coupling reactions, Dehydration reaction, Suzuki coupling

Peer-Reviewed Papers
15

References

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