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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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Tetrahedron Letters, 48, 845-845 (2007)
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
Highly selective palladium-catalyzed aminocarbonylation and cross-coupling reactions on a cavitand scaffold
Csok, Z.; Takatsy, A.; Kollar, L.
Tetrahedron, 68, 2657-2661 (2012)
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