913836-26-7

Basic information

• Product Name: 4-CHLORO-3-NITROBENZENEBORONIC ACID, PINACOL ESTER 98
• Synonyms: 4-CHLORO-3-NITROBENZENEBORONIC ACID, PINACOL ESTER 98;4-Chloro-3-nitrobenzeneboronic acid, pinacol ester 98%;2-(4-Chloro-3-nitrophenyl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane
• CAS NO: 913836-26-7
• Molecular Formula: C₁₂H₁₅BClNO₄
• Molecular Weight: 283.5175
• Product Categories: blocks;BoronicAcids
• Mol File: 913836-26-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 56-58
• Boiling Point: 375.1°C at 760 mmHg
• Flash Point: 180.7°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 1.72E-05mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: Keep Cold
• CAS DataBase Reference: 4-CHLORO-3-NITROBENZENEBORONIC ACID, PINACOL ESTER 98(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-3-NITROBENZENEBORONIC ACID, PINACOL ESTER 98(913836-26-7)
• EPA Substance Registry System: 4-CHLORO-3-NITROBENZENEBORONIC ACID, PINACOL ESTER 98(913836-26-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 913836-26-7(Hazardous Substances Data)

Usage

General Description

4-CHLORO-3-NITROBENZENEBORONIC ACID, PINACOL ESTER 98 is a chemical compound used in organic synthesis and chemical research. It is a boronic acid pinacol ester, meaning it has a boronic acid functional group attached to a pinacol substituent. 4-CHLORO-3-NITROBENZENEBORONIC ACID, PINACOL ESTER 98 is commonly used as a reagent in Suzuki-Miyaura cross-coupling reactions, which are important in the synthesis of complex organic molecules. It is a highly pure form of the compound, with a purity of 98%, making it suitable for use in sensitive chemical reactions where impurities could interfere with the desired outcome.

InChI:InChI=1/C12H15BClNO4/c1-11(2)12(3,4)19-13(18-11)8-5-6-9(14)10(7-8)15(16)17/h5-7H,1-4H3

Upstream product

• 16588-24-2 4-bromo-1-chloro-2-nitrobenzene 
• 73183-34-3 bis(pinacol)diborane 
• 635-22-3 4-Chloro-3-nitroaniline 

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 
• 850567-56-5 2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenylamine 

Relevant articles and documents

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 pinacol arylboronates from aromatic amines: A metal-free transformation

A metal-free borylation process based on Sandmeyer-type transformation using arylamines derivatives as the substrates has been developed. Through optimization of the reaction conditions, this novel conversion can be successfully applied to a wide range of aromatic amines, affording borylation products in moderate to good yields. Various functionalized arylboronates, which are difficult to access by other methods, can be easily obtained with this metal-free transformation. Moreover, this transformation can be followed by Suzuki-Miyaura cross-coupling without purification of the borylation products, which enhances the practical usefulness of this method. A possible reaction mechanism involving radical species has been proposed.