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523976

Sigma-Aldrich

4-Hydroxyphenylboronic acid

≥95.0%

Synonym(s):

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

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About This Item

Linear Formula:
HOC6H4B(OH)2
CAS Number:
71597-85-8
Molecular Weight:
137.93
MDL number:
MFCD01074628
UNSPSC Code:
12352103
PubChem Substance ID:
24874383
NACRES:
NA.22

Quality Level

100

Assay

≥95.0%

form

solid

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

Related Categories

Application

4-Hydroxyphenylboronic acid can be used as a reactant in:
  • Suzuki-Miyaura coupling and Stille coupling reactions.
  • Palladium-catalyzed aminocarbonylation and cross-coupling reactions.
  • Suzuki reaction for preparation of bio-supported palladium nanoparticles as phosphine-free catalysts.
  • Cu2O-catalyzed aerobic oxidative cross-coupling of tetrazoles.

It can also be used to prepare/promote:
  • PDK1 inhibitory activity (cancer cell growth, survival, and tumorigenesis inhibitor).
  • Rod-like dendronized polymers containing 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.
  • Oligoarenes by Suzuki-Miyaura palladium-catalyzed cross-coupling.

Other Notes

Contains varying amounts of anhydride

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - 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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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3099
MKCR6377
MKCC1858
MKBR5910V
SHBC2051V

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Highly selective palladium-catalyzed aminocarbonylation and cross-coupling reactions on a cavitand scaffold
Csok, Z.; Takatsy, A.; Kollar, L.
Tetrahedron, 68, 2657-2661 (2012)
Synthetic approach to the chemical isostere of O-methyl honokiol
Cui, M.; Kim, H. S.
Synlett, 23, 311-313 (2012)
Zhaoyang Lu et al.
Soft matter, 12(17), 3860-3867 (2016-03-31)
The self-assembling behavior of coil-rod-coil molecules 1a, 1b, and 2a, 2b was investigated using DSC, POM, SAXS, and AFM in bulk and aqueous solutions. These molecules contain p-quinquephenyl groups as rod segments incorporating lateral hydroxyl or methoxyl groups in the
Stéphanie Blanchard et al.
Bioorganic & medicinal chemistry letters, 22(8), 2880-2884 (2012-03-23)
A series of 2-anilino substituted 4-aryl-8H-purines were prepared as potent inhibitors of PDK1, a serine-threonine kinase thought to play a role in the PI3K/Akt signaling pathway, a key mediator of cancer cell growth, survival and tumorigenesis. The synthesis, SAR and
Ishikawa, Shunpei; Manabe, Kei
Chemistry Letters (Jpn), 35, 164-165 (2006)
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