4-Chlorophenylboronic acid(contains varying amounts of Anhydride) - ≥98% , CAS No.1679-18-1

CAS: 1679-18-1 Cat. No.: C396376 Molecular Weight: 156.37 Beilstein Registry Number: 2936346 EC Number: 216-845-5

GRADE & PURITY ≥98%

Synonyms

NSC 25408 | 1-Methyl-3-(2-benzothiazolyl)urea | 4chlorophenylboronic acid | 4-Chlorophenylboronic acid | 4-chloro-phenylboronic acid | Acilan Orange G | Antifeeding compound 24,055 | B-(4-CHLOROPHENYL)BORONIC ACID | B-(4-CHLOROPHENYL)-BORONIC ACID | 4-Chl

Storage

Room temperature

Shipped In

Normal

Overview

Product Application：

4-Chlorophenylboronic acid can be used as a reactant in: Palladium-catalyzed direct arylation. Cyclopalladation. Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation. Copper-mediated ligandless aerobic fluoroalkylation. Pd-catalyzed arylative cyclization. Ruthenium catalyzed direct arylation. Ligand-free copper-catalyzed coupling reactions. Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions. It can also be used to prepare: Substituted diarylmethylidenefluorenes via Suzuki coupling reaction. Baclofen lactam by Suzuki coupling of a pyrrolinyl tosylate, followed by hydrogenation reaction. Palladium(II) thiocarboxamide complexes as Suzuki coupling catalysts. Biaryls by Suzuki reactions of aryl chlorides, bromides, and iodides with arylboronic acids.

Specifications

Synonyms

NSC 25408 | 1-Methyl-3-(2-benzothiazolyl)urea | 4chlorophenylboronic acid | 4-Chlorophenylboronic acid | 4-chloro-phenylboronic acid | Acilan Orange G | Antifeeding compound 24, 055 | B-(4-CHLOROPHENYL)BORONIC ACID | B-(4-CHLOROPHENYL)-BORONIC ACID | 4-Chl

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504754797
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504754797
• Canonical Smiles: B(C1=CC=C(C=C1)Cl)(O)O
• IUPAC Name: (4-chlorophenyl)boronic acid
• InChIKey: CAYQIZIAYYNFCS-UHFFFAOYSA-N
• INCHI: 1S/C6H6BClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
• Isomeric SMILES: B(C1=CC=C(C=C1)Cl)(O)O
• WGK Germany: 3
• RTECS: CY8950000
• Molecular Weight: 156.37
• Beilstein: 2936346
• Reaxy-Rn: 2936346
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2936346&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: Chlorobenzenes
• Alternative Parents: Aryl chlorides Boronic acids Organic metalloid salts Organochlorides Organoboron compounds Organic oxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Chlorobenzene - Aryl halide - Aryl chloride - Boronic acid - Boronic acid derivative - Organic metalloid salt - Organic oxygen compound - Hydrocarbon derivative - Organic salt - Organochloride - Organoboron compound - Organohalogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
• 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)

KB (17409 Activities)

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

ENPP2 Tchem Autotaxin (2645 Activities)

Discover Target: ENPP2

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

Associated Targets(non-human)

Staphylococcus aureus (210822 Activities)

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: water-solubility 2.5 g/100 mL
• Melt Point(°C): 268-277℃
• Molecular Weight: 156.380 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 156.015 Da
• Monoisotopic Mass: 156.015 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. 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]

2. Jiayin Gao, Yaoyao Wang, Yuqing Yu, Mengxiang Zhu, Wen Kong, Genyan Liu, Xiaogang Luo.  (2024)  Carbonized cellulose microspheres loaded with Pd NPs as catalyst in p-nitrophenol reduction and Suzuki-Miyaura coupling reaction.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:38688337] [10.1016/j.ijbiomac.2024.131904]