4-Fluorophenylboronic acid - ≥99% , CAS No.1765-93-1

CAS: 1765-93-1 Cat. No.: F111213 Molecular Weight: 139.92 Beilstein Registry Number: 2829653 EC Number: 605-778-0

GRADE & PURITY ≥99%

Synonyms

4-Fluorobenzeneboronic acid | NSC 142683

Storage

Room temperature

Shipped In

Normal

Overview

4-Fluorophenylboronic acid can be used as a reactant in coupling reactions with arenediazonium tetrafluoroborates, iodonium salts, and iodanes. It is also used to make novel biologically active terphenyls.
It can also be used as a reactant in: Suzuki coupling using microwave and triton B catalyst. Pd-catalyzed direct arylation of pyrazoles with phenylboronic acids. Mizoroki-Heck and Suzuki-Miyaura coupling reactions catalyzed by palladium nanoparticles. Cu-catalyzed Petasis reactions. Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence. Ruthenium catalyzed direct arylation. Rh-catalyzed asymmetric conjugate additions. Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids. Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions. Suzuki cross-coupling of tetrabromothiophene. Palladium-catalyzed addition to nitriles.

Specifications

Synonyms

4-Fluorobenzeneboronic acid | NSC 142683

Specifications & Purity

≥99%

Storage

Room temperature

Shipped In

Normal

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488189274
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488189274
• Canonical Smiles: B(C1=CC=C(C=C1)F)(O)O
• IUPAC Name: (4-fluorophenyl)boronic acid
• InChIKey: LBUNNMJLXWQQBY-UHFFFAOYSA-N
• INCHI: 1S/C6H6BFO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
• Isomeric SMILES: B(C1=CC=C(C=C1)F)(O)O
• WGK Germany: 3
• Molecular Weight: 139.92
• Beilstein: 2829653
• Reaxy-Rn: 2829653
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2829653&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: Fluorobenzenes
• Alternative Parents: Aryl fluorides Boronic acids Organic metalloid salts Organofluorides Organoboron compounds Organic oxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Fluorobenzene - Aryl halide - Aryl fluoride - Boronic acid - Boronic acid derivative - Organic metalloid salt - Organic oxygen compound - Hydrocarbon derivative - Organic salt - Organofluoride - Organoboron compound - Organohalogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as fluorobenzenes. These are compounds containing one or more fluorine atoms attached to a benzene ring.
• External Descriptors: organofluorine compound

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)

MGLL Tchem Monoglyceride lipase (1909 Activities)

Discover Target: MGLL

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

Discover Target: ampC

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Faah Anandamide amidohydrolase (3907 Activities)

Discover Target: Faah

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Slightly soluble in water
• Melt Point(°C): 262-265°C
• Molecular Weight: 139.920 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 140.044 Da
• Monoisotopic Mass: 140.044 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. Jiayi Wang, Yicen Ge, Yue Wang, Rui Sun, Xiao Yang, Haodan Xue, Xiaoyan Ma, Jinyu Liu, Keling Hu.  (2023)  Pd nanoparticles supported in PDMAEMA-b-PLMA micelles: A superb catalytic platform for Suzuki-Miyaura cross-coupling in water.  EUROPEAN POLYMER JOURNAL,      [PMID:] [10.1016/j.eurpolymj.2023.112650]

2. Qi Wei, Luo Kexin, Su Qing, Sun Xiaoman, Li Xiaodong, Liu Ziqian, Wu Qiaolin.  (2022)  The Photoactive Hydrazone-Linked Covalent Organic Frameworks for Photocyclization Approach to Phenanthridine Derivatives.  CATALYSIS LETTERS,  153  (8): (2331-2340).  [PMID:] [10.1007/s10562-022-04162-5]

3. Qiuyu Lin, Luyun Xue, Jiannan Sun, Yuanchao Wang, Heyong Cheng.  (2022)  Suzuki C–C Coupling in Paper Spray Ionization: Microsynthesis of Biaryls and High-Sensitivity MS Detection of Aryl Bromides.  JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY,      [PMID:36074999] [10.1021/jasms.2c00192]

4. Xu-Dong Gao, Yue Hu, Wei-Feng Wang, Xiao-Bo Zhao, Xin-Zhen Du, Yan-Ping Shi.  (2022)  Rapid and Selective 19F NMR-Based Sensors for Fingerprint Identification of Ribose.  ANALYTICAL CHEMISTRY,      [PMID:35968680] [10.1021/acs.analchem.2c01832]

5. 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]

6. Kai Hu, Tiantian Pang, Yanmei Shi, Pengzhao Han, Yuanqing Zhao, Wenjie Zhao, Huahui Zeng, Shusheng Zhang, Zhenqiang Zhang.  (2021)  Magnetic borate-modified Mxene: A highly affinity material for the extraction of catecholamines.  ANALYTICA CHIMICA ACTA,      [PMID:34399896] [10.1016/j.aca.2021.338769]

7. Li Zhang, Wen-Huan Dong, Ning-Zhao Shang, Cheng Feng, Shu-Tao Gao, Chun Wang.  (2015)  N-Doped porous carbon supported palladium nanoparticles as a highly efficient and recyclable catalyst for the Suzuki coupling reaction.  CHINESE CHEMICAL LETTERS,      [PMID:] [10.1016/j.cclet.2015.08.007]

8. Li Zhang, Cheng Feng, Shutao Gao, Zhi Wang, Chun Wang.  (2014)  Palladium nanoparticle supported on metal–organic framework derived N-decorated nanoporous carbon as an efficient catalyst for the Suzuki coupling reaction.  CATALYSIS COMMUNICATIONS,      [PMID:] [10.1016/j.catcom.2014.12.004]

9. Hangqi Shi, Zhuowei Gu, Xiao Gu, Hongbin Pan, Junying Pan, Xiaolian Hu, Congcheng Fan, Minmin Shi, Hongzheng Chen.  (2013)  Effect of end-groups on the photovoltaic property of diphenyl substituted diketopyrrolopyrrole derivatives.  SYNTHETIC METALS,      [PMID:] [10.1016/j.synthmet.2013.11.024]

10. Zhiyu Zhang, Cheng Yang, Di Zhao, Yuanqing Zhao, Lixin Li, Zhonghua Li, Zhenqiang Zhang, Kai Hu.  (2024)  Boric Acid Functionalized Hypercrosslinked Polymers for Selective Extraction of Trace Catecholamines and Their Metabolites in Rat Serum.  JOURNAL OF SEPARATION SCIENCE,  47  (18): (e202400418).  [PMID:39304642] [10.1002/jssc.202400418]

11. Yunfeng Yuan, Xiaoge Wang, Jinhua Zhu, Abdelhadi El Jaouhari, Xiuhua Liu, Md． Zaved H． Khan.  (2025)  Phenylboronic acid functionalized magnetic ferroferric oxide nanoparticles and capillary electrophoresis for efficient isolation of flavonoid compounds from leaves of Lonicera japonica Thunb.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:39884071] [10.1016/j.chroma.2025.465729]