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523968

Sigma-Aldrich

3-Hydroxyphenylboronic acid

≥95.0%

Synonym(s):

3-Hydroxybenzeneboronic acid, m-Hydroxybenzeneboronic acid

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About This Item

Linear Formula:
HOC6H4B(OH)2
CAS Number:
87199-18-6
Molecular Weight:
137.93
MDL number:
MFCD01074603
UNSPSC Code:
12352103
PubChem Substance ID:
24874382
NACRES:
NA.22

Quality Level

100

Assay

≥95.0%

mp

210-213 °C (dec.) (lit.)

SMILES string

OB(O)c1cccc(O)c1

InChI

1S/C6H7BO3/c8-6-3-1-2-5(4-6)7(9)10/h1-4,8-10H

InChI key

WFWQWTPAPNEOFE-UHFFFAOYSA-N

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Application

3-Hydroxyphenylboronic acid (3-HPBA) can be used as a reagent:
  • In Suzuki-Miyaura coupling reactions with aryl halides for the formation of C-C bond in the presence of Pd catalyst.
  •  To synthesize boron/nitrogen-doped polymer nano/microspheres by hydrothermal polymerization with formaldehyde and ammonia.      
  • To prepare carbon quantum dots based on 3-HPBA as selective fructose sensor.     
  • In the development of modified electrodes for electrochemical biosensors.

Footnote

Contains varying amounts of anhydride

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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Synthesis of hyperbranched polythiophene with a controlled degree of branching via catalyst-transfer Suzuki-Miyaura coupling reaction
Segawa Y, et al.
Polym. Chem., 4(4), 1208-1215 (2013)
Diana M A Crista et al.
Journal of fluorescence, 29(1), 265-270 (2019-01-07)
The selective fluorescence sensing of fructose was achieved by fluorescence quenching of the emission of hydrothermal-synthesized carbon quantum dots prepared by 3-hydroxyphenylboronic acid. Quantification of fructose was possible in aqueous solutions with pH of 9 (Limit of Detection LOD and
Pierangelo Bellio et al.
Life sciences, 241, 117116-117116 (2019-12-04)
LexA protein is a transcriptional repressor which regulates the expression of more than 60 genes belonging to the SOS global regulatory network activated by damages to bacterial DNA. Considering its role in bacteria, LexA represents a key target to counteract

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