1314141-37-1

Basic information

• Product Name: (3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol
• Synonyms: (3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol
• CAS NO: 1314141-37-1
• Molecular Formula: C₁₃H₁₈BFO₃
• Molecular Weight: 252.0896232
• Mol File: 1314141-37-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate (Slightly)
• CAS DataBase Reference: (3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol(1314141-37-1)
• EPA Substance Registry System: (3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol(1314141-37-1)

Safety Data

• Hazardous Substances Data: 1314141-37-1(Hazardous Substances Data)

Usage

Description

(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol is a phenylmethanol derivative featuring a phenyl ring with a fluorine atom and a boron-containing dioxaborolane group. This molecule, characterized by its four methyl groups attached to the dioxaborolane, is utilized in organic synthesis and medicinal chemistry for constructing complex organic molecules.

Uses

Used in Organic Synthesis:
(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol is used as a synthetic intermediate for the creation of complex organic molecules. Its unique structure, including the fluorine atom and the boron-containing group, allows for versatile reactions and the formation of diverse molecular architectures.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol serves as a key building block for the development of pharmaceutical compounds. Its incorporation into drug candidates can potentially enhance their efficacy, selectivity, and pharmacokinetic properties, contributing to the advancement of novel therapeutic agents.
It is crucial to handle (3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol with care due to its potential reactivity and toxicity, ensuring safe practices in research and industrial applications.

Upstream product

• 456-47-3 3-fluoro-benzenemethanol 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1352657-25-0 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 871126-22-6 (2-fluoro-4-formylphenyl)boronic acid 
• 222978-01-0 4-bromo-3-fluorobenzyl alcohol 
• 1331945-14-2 (2-fluoro-4-(hydroxymethyl)phenyl)boronic acid 

Downstream Products

• 1354789-16-4 4-[[[(ferrocenylamino)carbonyl]oxy]methyl]-2-fluorophenylboronic acid pinacol ester 
• 1544673-59-7 2-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]isoindoline-1,3-dione 
• 1544673-76-8 [3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine 
• 1404094-89-8 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl carbonochloridate 

Relevant articles and documents

Aminoferrocene-based prodrugs activated by reactive oxygen species

Cancer cells generally generate higher amounts of reactive oxygen species than normal cells. On the basis of this difference, prodrugs have been developed (e.g., hydroxyferrocifen), which remain inactive in normal cells, but become activated in cancer cel

Synthesis and Evaluation of Hydrogen Peroxide Sensitive Prodrugs of Methotrexate and Aminopterin for the Treatment of Rheumatoid Arthritis

A series of novel hydrogen peroxide sensitive prodrugs of methotrexate (MTX) and aminopterin (AMT) were synthesized and evaluated for therapeutic efficacy in mice with collagen induced arthritis (CIA) as a model of chronic rheumatoid arthritis (RA). The prodrug strategy selected is based on ROS-labile 4-methylphenylboronic acid promoieties linked to the drugs via a carbamate linkage or a direct C-N bond. Activation under pathophysiological concentrations of H2O2 proved to be effective, and prodrug candidates were selected in agreement with relevant in vitro physicochemical and pharmacokinetic assays. Selected candidates showed moderate to good solubility, high chemical and enzymatic stability, and therapeutic efficacy comparable to the parent drugs in the CIA model. Importantly, the prodrugs displayed the expected safer toxicity profile and increased therapeutic window compared to MTX and AMT while maintaining a comparable therapeutic efficacy, which is highly encouraging for future use in RA patients.

Synthesis of boron-containing primary amines

In this study, boron-containing primary amines were synthesized for use as building blocks in the study of peptoids. In the first step, Gabriel synthesis conditions were modified to enable the construction of seven different aminomethylphenyl boronate esters in good to excellent yields. These compounds were further utilized to build peptoid analogs via an Ugi four-component reaction (Ugi-4CR) under microwave irradiation. The prepared Ugi-4CR boronate esters were then successfully converted to the corresponding boronic acids. Finally, the peptoid structures were successfully modified by cross-coupling to aryl/heteroaryl chlorides via a palladium-mediated Suzuki coupling reaction to yield the corresponding derivatives in moderate to good yields.