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523976

Sigma-Aldrich

4-Hydroxyphenylboronic acid

≥95.0%

Sinónimos:

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

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About This Item

Fórmula lineal:
HOC6H4B(OH)2
Número de CAS:
71597-85-8
Peso molecular:
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

Categorías relacionadas

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

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
MKCW3099
MKCR6377
MKCC1858
MKBR5910V
SHBC2051V

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Tetrahedron Letters, 48, 845-845 (2007)
Scott E Denmark et al.
Journal of the American Chemical Society, 128(50), 15958-15959 (2006-12-15)
The cross-coupling of geometrically defined (E)- and (Z)-alkenyl- and styrylsilanolates with a wide variety of aromatic and heteroaromatic chlorides has been achieved. Under catalysis by bulky, biphenyl-derived phosphines and allylpalladium chloride, the (preformed, stable) potassium salts of di-, tri- and
Ishikawa, Shunpei; Manabe, Kei
Chemistry Letters (Jpn), 35, 164-165 (2006)
Yu Li et al.
Chemical communications (Cambridge, England), 48(21), 2719-2721 (2012-02-04)
We present a new protocol that allows for the synthesis of 2,5-disubstituted tetrazoles via the direct coupling of N-H free tetrazoles and low toxic boronic acids in the presence of only a catalytic amount of Cu(2)O (5 mol%) as catalyst
Synthesis of Rod-Like Dendronized Polymers Containing G4 and G5 Ester Dendrons via Macromonomer Approach by Living ROMP
Kim, K.O.; Choi, T-L.
ACS Macro Letters, 1, 445-448 (2012)
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