4-Acetylbenzeneboronic Acid (contains varying amounts of Anhydride) - ≥98% , CAS No.149104-90-5

CAS: 149104-90-5 Cat. No.: A100554 Molecular Weight: 163.97 EC Number: 629-086-3

GRADE & PURITY ≥98%

Synonyms

AM808105 | STL554241 | 4-acetyl-phenyl boronic acid | 1-[4-(Dihydroxyboranyl)Phenyl]Ethan-1-One | 4-actylphenylboronic acid | MFCD01074667 | p-acetylphenylboronic acid | OBQRODBYVNIZJU-UHFFFAOYSA-N | 4-acetyl phenyl boronic acid | p-acetylbenzeneboronic a

Storage

Argon charged,Room temperature

Shipped In

Normal

Overview

4-Acetylphenylboronic acid is a boronate, belongs to a class of synthetic organic compounds. It reacts rapidly with peroxynitrite (ONOO(-)) to form stable hydroxy derivatives.It undergoes Suzuki coupling with 4-bromotriphenylamine catalyzed by dichlorobis(triphenylphosphine)Pd(II), during the synthesis of dendrimers
Application
4-Acetylphenylboronic acid was used in the synthesis of 4′-azidoacetophenone.
Reactant involved in:
Palladium-catalyzed decarboxylative coupling
Copper-catalyzed hydroxylation
Palladium-catalyzed Suzuki-Miyaura cross-coupling
Cross-coupling with α-bromocarbonyl compounds
Oxidation catalyzed by Baeyer-Villiger monooxygenases
1,5-substitution reactions

Specifications

Synonyms

AM808105 | STL554241 | 4-acetyl-phenyl boronic acid | 1-[4-(Dihydroxyboranyl)Phenyl]Ethan-1-One | 4-actylphenylboronic acid | MFCD01074667 | p-acetylphenylboronic acid | OBQRODBYVNIZJU-UHFFFAOYSA-N | 4-acetyl phenyl boronic acid | p-acetylbenzeneboronic a

Specifications & Purity

≥98%

Storage

Argon charged, Room temperature

Shipped In

Normal

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488194518
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488194518
• Canonical Smiles: B(C1=CC=C(C=C1)C(=O)C)(O)O
• IUPAC Name: (4-acetylphenyl)boronic acid
• InChIKey: OBQRODBYVNIZJU-UHFFFAOYSA-N
• INCHI: 1S/C8H9BO3/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-5,11-12H,1H3
• Isomeric SMILES: B(C1=CC=C(C=C1)C(=O)C)(O)O
• WGK Germany: 3
• Molecular Weight: 163.97
• Reaxy-Rn: 7869162
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7869162&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Aryl ketones
            • Level7 Phenylketones
              • Level8 Alkyl-phenylketones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Aryl ketones - Phenylketones
• Direct Parent: Alkyl-phenylketones
• Alternative Parents: Acetophenones Benzoyl derivatives Aryl alkyl ketones Boronic acids Organic metalloid salts Organometalloid compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alkyl-phenylketone - Acetophenone - Aryl alkyl ketone - Benzoyl - Benzenoid - Monocyclic benzene moiety - Boronic acid - Boronic acid derivative - Organic metalloid salt - Organic oxide - Hydrocarbon derivative - Organic metalloid moeity - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
• 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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Insoluble in water; Soluble in Methanol
• Sensitivity: Moisture sensitive.
• Melt Point(°C): 243-247°C
• Molecular Weight: 163.970 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 164.064 Da
• Monoisotopic Mass: 164.064 Da
• Topological Polar Surface Area: 57.500 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 162.000
• 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. Qing Wan, Meiying Liu, Dazhuang Xu, Hongye Huang, Liucheng Mao, Guangjian Zeng, Fengjie Deng, Xiaoyong Zhang, Yen Wei.  (2016)  Facile fabrication of amphiphilic AIE active glucan via formation of dynamic bonds: self assembly, stimuli responsiveness and biological imaging.  Journal of Materials Chemistry B,  4  (22): (4033-4039).  [PMID:32263102] [10.1039/C6TB00776G]