Production Method 1

635-22-3

73183-34-3

850567-56-5

Reaction Conditions

1.1 Reagents: tert-Butyl nitrite Catalysts: Benzoyl peroxide Solvents: Acetonitrile ;  4 h, rt
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: 1,2-Dichloroethane ;  4 h, rt

Reference

Synthesis of Trimethylstannyl Arylboronate Compounds by Sandmeyer-Type Transformations and Their Applications in Chemoselective Cross-Coupling Reactions

Qiu, Di; et al, Journal of Organic Chemistry, 2014, 79(5), 1979-1988

Production Method 2

913836-26-7

850567-56-5

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: 1,2-Dichloroethane ;  4 h, rt

Reference

Synthesis of Trimethylstannyl Arylboronate Compounds by Sandmeyer-Type Transformations and Their Applications in Chemoselective Cross-Coupling Reactions

Qiu, Di; et al, Journal of Organic Chemistry, 2014, 79(5), 1979-1988

Production Method 3

73183-34-3

850567-56-5

721960-43-6

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: 1,4-Dioxane ;  16 h, 70 °C

Reference

Para-Selective C-H Borylation of Common Arene Building Blocks Enabled by Ion-Pairing with a Bulky Countercation

Mihai, Madalina T.; et al, Journal of the American Chemical Society, 2019, 141(39), 15477-15482

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

• 4-Chloro-3-nitroaniline
• Bis(pinacolato)diborane
• 4-Chloro-3-nitrophenylboronic acid, pinacol ester

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

• 2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (850567-56-5)
• 2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (721960-43-6)

• 1. An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile?
  Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo Nam Dalton Trans., 2016,45, 376-383
• 2. An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction?
  Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin Jin J. Mater. Chem. C, 2020,8, 192-200
• 3. An all-solid-state asymmetric device based on a polyaniline hydrogel for a high energy flexible supercapacitor?
  Hamid Heydari,Mohammad B. Gholivand New J. Chem., 2017,41, 237-244
• 4. An algal process treatment combined with the Fenton reaction for high concentrations of amoxicillin and cefradine
  Haitao Li,Yu Pan,Zhizhi Wang,Shan Chen,Ruixin Guo,Jianqiu Chen RSC Adv., 2015,5, 100775-100782
• 5. An integrated microfluidic 3D tumor system for parallel and high-throughput chemotherapy evaluation?
  Dan Liu,Rui Hu,Zhongchao Huang,Meilin Sun,Kai Han Analyst, 2020,145, 6447-6455

Professional Introduction to 2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (CAS No. 850567-56-5)

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline is a sophisticated organic compound that has garnered significant attention in the field of pharmaceutical chemistry and materials science. This compound, identified by its CAS number 850567-56-5, is characterized by its unique structural features and versatile reactivity. The presence of both chloro and boronic ester functional groups makes it a valuable intermediate in the synthesis of various biologically active molecules.

The compound's structure consists of a benzene ring substituted with a chloro group at the 2-position and a boronic ester group at the 5-position. The boronic ester moiety is derived from 4,4,5,5-tetramethyl-1,3,2-dioxaborolane, a stable and highly reactive boronate ester known for its utility in Suzuki-Miyaura cross-coupling reactions. This reaction is a cornerstone in modern synthetic organic chemistry and has been widely employed in the construction of complex molecular architectures.

In recent years, the pharmaceutical industry has seen a surge in the development of targeted therapies for various diseases, including cancer and inflammatory disorders. The ability to efficiently construct complex heterocyclic compounds is crucial in this endeavor. 2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as an excellent precursor for such constructions due to its compatibility with palladium-catalyzed cross-coupling reactions.

One of the most notable applications of this compound is in the synthesis of small-molecule inhibitors that target specific enzymatic pathways. For instance, researchers have utilized derivatives of 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline to develop inhibitors of kinases and other critical enzymes involved in disease progression. These inhibitors have shown promise in preclinical studies and are being explored for their potential therapeutic efficacy.

The boronic ester group in 2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline is particularly advantageous because it can undergo facile coupling with aryl halides or triflates under mild conditions. This reactivity has been leveraged to create novel biaryl structures that exhibit unique biological activities. For example, recent studies have demonstrated that compounds derived from this intermediate exhibit inhibitory effects on protein-protein interactions relevant to neurodegenerative diseases.

Moreover，the chloro substituent on the benzene ring provides an additional handle for further functionalization. It can be readily displaced by nucleophiles such as amines or thiols through nucleophilic aromatic substitution reactions. This allows for the diversification of the molecular scaffold and the exploration of new chemical space.

The synthesis of 2-Chloro-5-(4，4，5，5-tetramethyl-l，3，2-dioxaborolan-l，2-yI)aniline involves multiple steps that highlight its complexity and synthetic utility. Initially，the boronic ester group is introduced via lithiation followed by reaction with an organoboron reagent. Subsequent functionalization with a chlorinating agent completes the synthesis. This multi-step process underscores the compound's importance as a building block in organic synthesis.

In conclusion，the versatility and reactivity of 2-Chloro-l(4，4，s，s-tetramethyl-l，3，z-dioxaborolan-z-yI)aniline make it an indispensable tool in pharmaceutical research and development。 Its role as a precursor for biologically active molecules continues to be explored in both academic and industrial settings。 As synthetic methodologies evolve further，the applications of this compound are expected to expand even more significantly。

• 877160-63-9(3-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline)
• 870195-94-1(2-(2-Chlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1073371-77-3(4-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline)
• 850567-51-0(3-Aminophenylboronic acid, pinacol ester, hydrochloride)
• 68716-50-7(2,4-Dichlorophenylboronic acid, pinacol ester)
• 913836-26-7(4-Chloro-3-nitrophenylboronic acid, pinacol ester)
• 195062-61-4(4-Chlorophenylboronic acid, pinacol ester)
• 863578-21-6(5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)aniline)
• 1309982-17-9(2-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline)
• 721960-43-6(2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline)