Production Method 1

73183-34-3

1269233-11-5

863578-21-6

Reaction Conditions

1.1 Reagents: Dodecahydrotriphenylene Catalysts: 3,4,7,8-Tetramethyl-1,10-phenanthroline ,  Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium Solvents: Dichloromethane ,  Tetrahydrofuran ;  8 h, 80 °C; 80 °C → rt
1.2 Reagents: Oxygen ;  rt

Reference

A Traceless Directing Group for C-H Borylation

Preshlock, Sean M.; et al, Angewandte Chemie, 2013, 52(49), 12915-12919

Production Method 2

73183-34-3

25015-63-8

1269233-11-5

863578-21-6

Reaction Conditions

1.1 Reagents: Dodecahydrotriphenylene Catalysts: 3,4,7,8-Tetramethyl-1,10-phenanthroline ,  Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium Solvents: Dichloromethane ,  N-Methyl-2-pyrrolidone ;  8 h, 80 °C; 80 °C → rt
1.2 Reagents: Oxygen ;  rt

Reference

A Traceless Directing Group for C-H Borylation

Preshlock, Sean M.; et al, Angewandte Chemie, 2013, 52(49), 12915-12919

Production Method 3

25015-63-8

1269233-11-5

863578-21-6

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  1 h, rt
1.2 Catalysts: 3,4,7,8-Tetramethyl-1,10-phenanthroline ,  Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ;  16 h, 80 °C; 80 °C → rt
1.3 Reagents: Oxygen ;  rt

Reference

A Traceless Directing Group for C-H Borylation

Preshlock, Sean M.; et al, Angewandte Chemie, 2013, 52(49), 12915-12919

3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline Raw materials

• Bis(pinacolato)diborane
• Pinacolborane

3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline Preparation Products

• 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1269233-11-5)
• 5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)aniline (863578-21-6)

• 1. Emerging investigators
  Polym. Chem., 2015,6, 5501-5502
• 2. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 3. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 4. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 5. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147

Recent Advances in the Application of 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (CAS: 1269233-11-5) in Chemical Biology and Pharmaceutical Research

The compound 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (CAS: 1269233-11-5) has recently emerged as a key intermediate in the synthesis of novel pharmaceutical agents and chemical probes. This boronic acid derivative exhibits unique reactivity due to the presence of both an amine and a boronate ester functional group, making it a versatile building block for Suzuki-Miyaura cross-coupling reactions. Recent studies have highlighted its potential in targeted drug discovery, particularly in the development of kinase inhibitors and proteolysis targeting chimeras (PROTACs).

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of this compound in the synthesis of BTK (Bruton's tyrosine kinase) inhibitors. Researchers utilized the boronate ester moiety for efficient coupling with various heteroaryl halides, yielding potent inhibitors with improved pharmacokinetic properties. The chloro and amino substituents on the aromatic ring provided additional sites for further functionalization, allowing for fine-tuning of molecular properties. This work underscores the compound's value in structure-activity relationship (SAR) studies for kinase-targeted therapeutics.

In the field of chemical biology, 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline has been employed as a precursor for the development of activity-based probes. A recent Nature Chemical Biology publication described its incorporation into fluorescent probes for monitoring protease activity in live cells. The boronate group served as a reactive handle for subsequent bioconjugation, while the aromatic system provided the scaffold for fluorophore attachment. This dual functionality makes the compound particularly valuable for creating multifunctional molecular tools.

From a synthetic chemistry perspective, the stability of the pinacol boronate ester in 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline has been a subject of recent investigation. A 2024 ACS Catalysis paper reported optimized conditions for its storage and handling, revealing that proper anhydrous conditions can significantly extend its shelf life. This is particularly important for large-scale pharmaceutical manufacturing where consistent quality of intermediates is crucial.

Looking forward, the unique properties of 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline position it as a promising candidate for emerging therapeutic modalities. Current research is exploring its application in the development of covalent inhibitors, where the chloro substituent can serve as a potential electrophilic warhead. Additionally, its potential in radiopharmaceutical development is being investigated, leveraging the boron atom for potential neutron capture therapy applications.

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