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Usage

Uses

Used in Organic Synthesis:
3-Amino-4-Chlorophenylboronic Acid, Pinacol Ester is used as a key intermediate for the synthesis of various organic compounds. Its boronic acid pinacol ester functional group facilitates Suzuki coupling reactions, which are essential for forming carbon-carbon bonds in complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-Amino-4-Chlorophenylboronic Acid, Pinacol Ester is used as a building block for the development of new drugs. Its reactivity and stability make it a valuable component in the creation of biologically active compounds, which can be further modified to target specific therapeutic applications.
Used in Chemical Research:
3-Amino-4-Chlorophenylboronic Acid, Pinacol Ester is employed as a research tool in the study of chemical reactions and mechanisms. Its unique properties allow chemists to explore new reaction pathways and develop innovative synthetic strategies for the preparation of complex molecules.

InChI:InChI=1/C12H17BClNO2/c1-11(2)12(3,4)17-13(16-11)8-5-6-9(14)10(15)7-8/h5-7H,15H2,1-4H3

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 913836-26-7 2-(4-Chloro-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 95-51-2 o-chloroaniline 

Downstream Products

• 1417036-35-1 2,2′-(4-chloro-1,3-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 1565857-78-4 (2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)trimethylstannane 
• 1400287-53-7 2-chloro-4-(pyrazin-2-yl)aniline 
• 1400287-54-8 2-chloro-4-(pyrimidin-5-yl)aniline 
• 1341981-04-1 2-chloro-5-(1-methyl-1H-pyrazol-4-yl)aniline 

Relevant academic research and scientific papers

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

The selective functionalization of C-H bonds at the arene para position is highly challenging using transition metal catalysis. Iridium-catalyzed borylation has emerged as a leading technique for arene functionalization, but there are only a handful of strategies for para-selective borylation, which operate on specific substrate classes and use bespoke ligands or catalysts. We describe a remarkably general protocol which results in para-selectivity on some of the most common arene building blocks (anilines, benzylamines, phenols, benzyl alcohols) and uses standard borylation ligands. Our strategy hinges upon the facile conversion of the substrates into sulfate or sulfamate salts, wherein the anionic arene component is paired with a tetrabutylammonium cation. We hypothesize that the bulk of this cation disfavors meta-C-H borylation, thereby promoting the challenging para-selective reaction.

A 3 - amino - 4 - chlorophenyl boronic acid [...] alcohol ester synthesis method (by machine translation)

The invention relates to a 3 - amino - 4 - chlorophenyl boronic acid [...] alcohol ester synthesis method. Mainly solves the technical problem of improving its yield. The invention synthetic method comprises the following steps: in [1, 1' - double-(diphenyl phosphino) ferrocene] palladium dichloride under the catalytic action of, 5 - bromo - 2 - chloro nitrobenzene in 1, 4 - dioxane and duplex [...] borate reaction, to obtain compound 1; compound 1 in ethanol and water in the mixed solution and ammonium chloride, iron powder reaction, nitro is reduced to the amino, to produce the target compound 2. As the expensive medicine intermediate, 3 - amino - 4 - chlorophenyl boronic acid ester in [...] widely applied in the pharmaceutical industry. (by machine translation)

Synthesis of trimethylstannyl arylboronate compounds by sandmeyer-type transformations and their applications in chemoselective cross-coupling reactions

A synthetic method based on Sandmeyer-type reactions to access both tin- and boron-substituted arenes from nitroaniline derivatives is described. This transformation can be applied to the synthesis of a series of functionalized trimethylstannyl arylboronates. In addition, the chemoselective reaction of the Stille and Suzuki-Miyaura cross-coupling reactions is explored, and a series of m- and p-terphenyl derivatives have been synthesized by conducting consecutive one-pot Stille and Suzuki-Miyaura cross-coupling reactions.