502622-85-7

Basic information

• Product Name: 4-Nitrophenylboronic acid neopentylglycol ester
• Synonyms: 5,5-dimethyl-2-(4-nitrophenyl)-1,3,2-dioxaborinane;1,3,2-Dioxaborinane, 5,5-dimethyl-2-(4-nitrophenyl)-
• CAS NO: 502622-85-7
• Molecular Formula: C₁₁H₁₄BNO₄
• Molecular Weight: 235.04416
• Mol File: 502622-85-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 368.1±25.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Nitrophenylboronic acid neopentylglycol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrophenylboronic acid neopentylglycol ester(502622-85-7)
• EPA Substance Registry System: 4-Nitrophenylboronic acid neopentylglycol ester(502622-85-7)

Safety Data

• Hazardous Substances Data: 502622-85-7(Hazardous Substances Data)

Usage

Description

4-Nitrophenylboronic acid neopentylglycol ester is a boronic acid derivative with the molecular formula C12H17BNO6. It is commonly used in organic synthesis and medicinal chemistry as a cross-coupling reagent. The neopentylglycol ester moiety enhances its stability and solubility, making it a valuable reagent in chemical and pharmaceutical research.

Uses

Used in Organic Synthesis:
4-Nitrophenylboronic acid neopentylglycol ester is used as a cross-coupling reagent for the formation of carbon-carbon bonds. It is particularly useful in the Suzuki-Miyaura coupling reaction, a widely employed method for the synthesis of biaryl compounds and other complex organic molecules.
Used in Medicinal Chemistry:
4-Nitrophenylboronic acid neopentylglycol ester is used as a building block in the development of new pharmaceutical compounds. Its unique structure and reactivity make it a promising candidate for the synthesis of potential antitumor and antiviral agents.
Used in Chemical Research:
4-Nitrophenylboronic acid neopentylglycol ester is used as a reagent in various chemical research applications. Its stability and solubility make it an attractive choice for studying the properties and reactions of boronic acid derivatives.
Used in Pharmaceutical Research:
4-Nitrophenylboronic acid neopentylglycol ester is used in the search for new therapeutic agents. Its potential antitumor and antiviral properties make it a valuable tool in the development of novel drugs for the treatment of various diseases.

Upstream product

• 586-78-7 para-nitrophenyl bromide 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 24067-17-2 4-nitrophenylboronic acid 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 1630-79-1 tetrakis(dimethylamido)diborane 
• 17763-80-3 para-nitrophenyl triflate 
• 668987-38-0 5,5-dimethyl-1,3,2-dioxaborinane 
• 100-00-5 4-chlorobenzonitrile 

Downstream Products

• 62-23-7 4-nitro-benzoic acid 
• 100-02-7 4-nitro-phenol 
• 93-89-0 benzoic acid ethyl ester 
• 99-77-4 ethyl 4-nitrobenzoate 
• 1380288-23-2 2,2,6,6-tetramethyl-1-(4-nitrophenyl)piperidine 
• 129077-51-6 4’-(4-nitrophenyl)-2,2’,6’,2’’-terpyridine 
• 29275-99-8 4-nitro-N,N-bis(propan-2-yl)aniline 

Relevant articles and documents

Pd II -Porphyrin Complexes - The First Use as Safer and Efficient Catalysts for Miyaura Borylation

We have developed a simple and convenient procedure for the preparation of pinacol arylboronates from aryl/heteroaryl bromides and bis(pinacolato)diborane using a Pd II -porphyrin complex as a catalyst. Seven different Pd II -porphyrin complexes (Pd II -T m HPP, Pd II -T m CPP, Pd II -TPP, Pd II -TST p SPP, Pd II -T p CPP, Pd II -T p TP, and Pd II -T p AP) have been synthesized and investigated for their catalytic influence in the Miyaura borylation.

Borylation of organo halides and triflates using tetrakis(dimethylamino) diboron

We report a new in situ borylation method using tetrakis(dimethylamino) diboron, DMA4B2, in the presence of a diol. Our method uses standard borylation conditions and readily available Pd-catalysts. The scope of this method includes aryl halides and triflates as well as vinyl halides and triflates. The method successfully works with a broad range of diols, enabling the selection of the best boronic ester for subsequent Suzuki coupling.

Two-step, one-pot ni-catalyzed neopentylglycolborylation and complementary pd/ni-catalyzed cross-coupling with aryl halides, mesylates, and tosylates

(Equation Presented) Two-step, one-pot neopentylglycolborylation of aryl iodides and bromides catalyzed by NiCl2(dppe) and NiCl 2(dppp) is reported. Electron-rich and electron-deficient aryl neopentylglycolboronates were efficiently cross-coupled with aryl iodides, bromides, chlorides, mesylates, and tosylates by exploiting complementary Pd/Ni and Ni/Ni catalysis. The borylation route was further extended to a three-step, one-pot synthesis of biaryls via in situ Ni-catalyzed borylation and Pd-mediated cross-coupling.