1003298-87-0

Basic information

• Product Name: 3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester
• Synonyms: 3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester;2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS NO: 1003298-87-0
• Molecular Formula: C₁₂H₁₅BCl₂O₃
• Molecular Weight: 306.97798
• Mol File: 1003298-87-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 108.0 to 112.0 °C
• Boiling Point: 103°C/0.3mmHg(lit.)
• Appearance: /
• Density: 1.28
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: 6.72±0.40(Predicted)
• CAS DataBase Reference: 3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester(1003298-87-0)
• EPA Substance Registry System: 3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester(1003298-87-0)

Safety Data

• Hazardous Substances Data: 1003298-87-0(Hazardous Substances Data)

Usage

Description

3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester is a boronic acid derivative used as a building block in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals. It features a phenyl ring with two chlorine atoms, a hydroxy group, and a boronic acid group, with the pinacol ester moiety enhancing its stability and solubility.

Uses

Used in Organic Synthesis:
3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester is used as a building block for the formation of various pharmaceuticals, agrochemicals, and fine chemicals due to its ability to form diverse molecular structures and functional groups.
Used in Suzuki-Miyaura Coupling Reactions:
In the field of organic chemistry, 3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester is used as a reagent in Suzuki-Miyaura coupling reactions, which are crucial for the formation of carbon-carbon bonds. This application is significant in the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
3,5-Dichloro-4-hydroxyphenylboronic acid pinacol ester is utilized as a key intermediate in the development of new pharmaceutical compounds, contributing to the creation of molecules with potential therapeutic properties.
Used in Agricultural Chemistry:
This chemical compound is also employed in the agricultural sector, where it serves as a precursor in the synthesis of agrochemicals, potentially leading to the development of new pesticides or other crop protection agents.

Upstream product

• 3217-15-0 4-bromo-2,6-dichloro-phenol 
• 73183-34-3 bis(pinacol)diborane 
• 1984-65-2 2,6-dichloroanisole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 1448361-79-2 (S)-tert-butyl 1-{5-[3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)-1,5-naphthyridin-4-ylamino]pyridin-2-yl}piperidin-3-ylcarbamate 

Relevant articles and documents

7-benzyl-4-(4-phenylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine derivatives and Composition for skin whitening and Pharmaceutical composition for use in preventing or treating disorders of Melanin Hyperpigmentation containing the same as an active ingredient

The present invention relates to a 7-benzyl-4(4-phenylpiperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine derivative, and to a composition for skin whitening, comprising the same as an active ingredient. Since the derivative exhibits the effect of inhibiting the production of melanin even when used in a small amount, it is useful as a pharmaceutical composition for preventing or treating melanin hyperpigmentation diseases, a cosmetic composition for skin whitening, and a health functional food for skin whitening.

Structure-Based Design of MptpB Inhibitors That Reduce Multidrug-Resistant Mycobacterium tuberculosis Survival and Infection Burden in Vivo

Mycobacterium tuberculosis protein-tyrosine-phosphatase B (MptpB) is a secreted virulence factor that subverts antimicrobial activity in the host. We report here the structure-based design of selective MptpB inhibitors that reduce survival of multidrug-resistant tuberculosis strains in macrophages and enhance killing efficacy by first-line antibiotics. Monotherapy with an orally bioavailable MptpB inhibitor reduces infection burden in acute and chronic guinea pig models and improves the overall pathology. Our findings provide a new paradigm for tuberculosis treatment.

Process for the synthesis of phenols from arenes

A process to synthesize substituted phenols such as those of the general formula RR′R″Ar(OH) wherein R, R′, and R″ are each independently hydrogen or any group which does not interfere in the process for synthesizing the substituted phenol including, but not limited to, halo, alkyl, alkoxy, carboxylic ester, amine, amide; and Ar is any variety of aryl or hetroaryl by means of oxidation of substituted arylboronic esters is described. In particular, a metal-catalyzed C—H activation/borylation reaction is described, which when followed by direct oxidation in a single or separate reaction vessel affords phenols without the need for any intermediate manipulations. More particularly, a process wherein Ir-catalyzed borylation of arenes using pinacolborane (HBPin) followed by oxidation of the intermediate arylboronic ester by OXONE is described.