Page last updated: 2024-12-08

1,4-phenylenebis(boronic acid)

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## 1,4-Phenylenebis(boronic acid): A Building Block for Advanced Materials

**1,4-Phenylenebis(boronic acid)**, also known as **1,4-benzenediboronic acid**, is an organic compound with the formula C₆H₄(B(OH)₂)₂. It consists of a benzene ring with two boronic acid groups (-B(OH)₂) attached at the 1 and 4 positions.

This molecule plays a crucial role in research due to its unique properties:

**1. Versatile Building Block:**

* **Suzuki-Miyaura Coupling:** The boronic acid groups are highly reactive, enabling 1,4-phenylenebis(boronic acid) to participate in **Suzuki-Miyaura coupling reactions**. This reaction is a powerful tool for creating complex organic molecules by joining aromatic rings with various other functionalities.

* **Polymer Synthesis:** 1,4-phenylenebis(boronic acid) can be used as a monomer to create **polymers** with specific properties. The rigid aromatic structure provides strength and thermal stability, while the boronic acid groups can be modified to introduce diverse functionalities.

**2. Applications in Materials Science:**

* **Organic Electronics:** 1,4-phenylenebis(boronic acid) is a key building block for **organic semiconductors**, which are used in devices like organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs).

* **Polymers for Medicine:** 1,4-phenylenebis(boronic acid) is incorporated into polymers for biomedical applications, such as drug delivery, tissue engineering, and bioimaging. The boronic acid groups can bind to sugars, providing specific targeting abilities.

* **Sensors and Catalysis:** 1,4-phenylenebis(boronic acid) is used in the development of **sensors** for detecting specific analytes, like sugars, and as a **catalyst** for organic reactions.

**3. Advantages:**

* **Easy to Synthesize:** 1,4-phenylenebis(boronic acid) is readily available commercially or can be synthesized with relatively simple procedures.

* **High Stability:** The compound exhibits good stability under various conditions, making it suitable for various applications.

**Overall, 1,4-phenylenebis(boronic acid) is a versatile and important building block for research in various fields, including organic synthesis, materials science, and medicine. Its ability to form stable bonds and its adaptable functionalities contribute to its wide range of applications in the development of advanced materials and technologies.**

1,4-phenylenebis(boronic acid): structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID230478
CHEMBL ID140916
SCHEMBL ID204921
MeSH IDM0556920

Synonyms (43)

Synonym
benzene-1,4-diboronic acid
nsc25410
p-benzenediboronic acid
4612-26-4
nsc-25410
benzene-1,4-diboronic acid, >=95.0%
1,4-benzenediboronic acid
NCGC00092017-01
1,4 phenyl diboronic acid
CHEMBL140916 ,
(4-boronophenyl)boronic acid
1,4-phenylenediboronic acid
P1358
bdbm50067903
AKOS004116070
1,4-phenylenebisboronic acid
A7211
1,4-phenylenebis(boronic acid)
1,4-phenylenediboronicacid
BCP9000038
FT-0606763
AM20040523
boronic acid, b,b'-1,4-phenylenebis-
AB05330
BODYVHJTUHHINQ-UHFFFAOYSA-N
1,4-benzene diboronic acid
benzene-1,4-diyldiboronic acid
1,4-phenylene diboronic acid
SCHEMBL204921
[4-(dihydroxyboranyl)phenyl]boronic acid
AS-3100
boronic acid, 1,4-phenylenebis-
mfcd00236018
CS-W000938
BBL102130
SY025269
STL555929
BCP22772
DTXSID20963507
p-phenylenebisboronic acid
676566-94-2
EN300-7363335
HY-W000938
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency16.36010.00419.984825.9290AID504444
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Beta-lactamaseEscherichia coli K-12Ki3.90000.02703.64137.3000AID38398
Angiotensin-converting enzymeRattus norvegicus (Norway rat)Ki3.90000.00011.96427.3000AID38398
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
antibiotic catabolic processBeta-lactamaseEscherichia coli K-12
response to antibioticBeta-lactamaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
beta-lactamase activityBeta-lactamaseEscherichia coli K-12
hydrolase activityBeta-lactamaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
outer membrane-bounded periplasmic spaceBeta-lactamaseEscherichia coli K-12
periplasmic spaceBeta-lactamaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID38398Inhibitory activity against Escherichia coli AmpC beta-lactamase.1998Journal of medicinal chemistry, Nov-05, Volume: 41, Issue:23
Structure-based enhancement of boronic acid-based inhibitors of AmpC beta-lactamase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (20.00)18.2507
2000's0 (0.00)29.6817
2010's3 (60.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.66

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.66 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.66)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]