4-Bromophenylboronic acid (contains varying amounts of Anhydride) - ≥98% , CAS No.5467-74-3

CAS: 5467-74-3 Cat. No.: B396370 Molecular Weight: 200.83 Beilstein Registry Number: 2936347 EC Number: 226-779-9

GRADE & PURITY ≥98%

Synonyms

4-Bromobenzeneboronic acid | 4-bromo-benzeneboronic acid | 4-Bromophenylboronic Acid-d4 (contains varying amounts of Anhydride) | WLN: QBQR DE | Boronic acid, (4-bromophenyl)- | NCGC00092014-02 | p-bromo phenylboronic acid | 4bromobenzene boronic acid | 4

Storage

Room temperature,Argon charged

Shipped In

Normal

Overview

Palladium catalyzed Suzuki-Miyaura cross-couplings;Pd(II)-catalyzed diastereoselective conjugate additions； Palladium-catalyzed stereoselective Heck-type reaction of allylic esters with arylboronic acids；

Specifications

Synonyms

4-Bromobenzeneboronic acid | 4-bromo-benzeneboronic acid | 4-Bromophenylboronic Acid-d4 (contains varying amounts of Anhydride) | WLN: QBQR DE | Boronic acid, (4-bromophenyl)- | NCGC00092014-02 | p-bromo phenylboronic acid | 4bromobenzene boronic acid | 4

Specifications & Purity

≥98%

Storage

Room temperature, Argon charged

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504755388
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504755388
• Canonical Smiles: B(C1=CC=C(C=C1)Br)(O)O
• IUPAC Name: (4-bromophenyl)boronic acid
• InChIKey: QBLFZIBJXUQVRF-UHFFFAOYSA-N
• INCHI: 1S/C6H6BBrO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
• Isomeric SMILES: B(C1=CC=C(C=C1)Br)(O)O
• WGK Germany: 3
• RTECS: CY8650000
• Molecular Weight: 200.83
• Beilstein: 2936347
• Reaxy-Rn: 2936347
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2936347&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Halobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Bromobenzenes
• Alternative Parents: Aryl bromides Boronic acids Organic metalloid salts Organobromides Organoboron compounds Organic oxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Bromobenzene - Aryl halide - Aryl bromide - Boronic acid - Boronic acid derivative - Organic metalloid salt - Organic oxygen compound - Hydrocarbon derivative - Organic salt - Organobromide - Organoboron compound - Organohalogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as bromobenzenes. These are organic compounds containing a bromine atom attached to a benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CA2 Tclin Carbonic anhydrase II (17698 Activities)

Discover Target: CA2

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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CA1 Tclin Carbonic anhydrase I (13240 Activities)

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KB (17409 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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Associated Targets(non-human)

bla Beta-lactamase TEM (457 Activities)

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ampC Beta-lactamase AmpC (62480 Activities)

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Carbonic anhydrase (69 Activities)

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Staphylococcus aureus (210822 Activities)

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Subtilisin (36 Activities)

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norA Quinolone resistance protein norA (2171 Activities)

Discover Target: norA

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in methanol. Insoluble in water.
• Sensitivity: Hygroscopic
• Melt Point(°C): 284-288°C
• Molecular Weight: 200.830 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 199.964 Da
• Monoisotopic Mass: 199.964 Da
• Topological Polar Surface Area: 40.500 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 102.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

References

1. Feng Li, Kai-Qi Liu, Wen-Juan Wang, Zhen-Tao Jiang, Fen-Ying Kong, Heng-Ye Li, Zhong-Xia Wang, Wei Wang.  (2023)  Selective identification of p-nitroaniline by bromine-mediated polarization of carbon dots.  ANALYST,  149  (4): (1212-1220).  [PMID:38214602] [10.1039/D3AN02080K]

2. Lingfeng Xu, Yanrong Huang, Xinkang Peng, Kui Wu, Chunfang Huang, Limin Liu.  (2022)  A near-infrared intelligent molecular rotor with aggregation induced-emission for viscosity detection of liquids.  Materials Advances,  3  (8): (3545-3553).  [PMID:] [10.1039/D2MA00024E]

3. Shufang Liu, Ziqian Liu, Qing Su, Qiaolin Wu.  (2022)  Multifunctional covalent organic frameworks for photocatalytic oxidative hydroxylation of arylboronic acids and fluorescence sensing for Cu2+.  MICROPOROUS AND MESOPOROUS MATERIALS,      [PMID:] [10.1016/j.micromeso.2022.111737]

4. Jiangnan Wang, Zixi Zheng, Lu Liu, Jianming Pan.  (2025)  Self-diffusing halloysite-based adsorbent for efficient and selective lead removal.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2025.135651]