1398923-95-9

Basic information

• Product Name: 4-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• Synonyms: 2-Fluoro-5-hydroxyphenylboronic acid, pinacol ester;4-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;2-Fluoro-5-hydroxyphenylboronic acid, pinacol ester（WS202800）
• CAS NO: 1398923-95-9
• Molecular Formula: C₁₂H₁₆BFO₃
• Molecular Weight: 238.0630432
• Mol File: 1398923-95-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 354.1±32.0 °C(Predicted)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.02±0.18(Predicted)
• CAS DataBase Reference: 4-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol(1398923-95-9)
• EPA Substance Registry System: 4-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol(1398923-95-9)

Safety Data

• Hazardous Substances Data: 1398923-95-9(Hazardous Substances Data)

Usage

General Description

4-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol is a chemical compound that consists of a phenol group with a fluorine atom attached to the third carbon and a boron atom attached to the fourth carbon through a dioxaborolane ring. 4-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol is commonly used in the field of organic chemistry as a reagent in various synthetic reactions, including Suzuki-Miyaura cross-coupling reactions. It is known for its ability to facilitate the formation of carbon-carbon bonds, making it a valuable tool for the construction of complex organic molecules. The tetramethyl substitution on the dioxaborolane ring increases the stability and reactivity of the compound, making it a versatile and efficient reagent for organic synthesis.

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1150114-52-5 (2-fluoro-5-hydroxyphenyl)boronic acid 

Downstream Products

• 1398923-93-7 2-[2-fluoro-5-(tetrahydro-furan-2-ylmethoxy)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 

Relevant articles and documents

Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate-Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions

A strategy for affecting ortho versus meta/para selectivity in Ir-catalyzed C-H borylations (CHBs) of phenols is described. From selectivity observations with ArylOBpin (pin = pinacolate), it is hypothesized that an electrostatic interaction between the partial negatively charged OBpin group and the partial positively charged bipyridine ligand of the catalyst favors ortho selectivity. Experimental and computational studies designed to test this hypothesis support it. From further computational work a second generation, in silico designed catalyst emerged, where replacing Bpin with Beg (eg = ethylene glycolate) was predicted to significantly improve ortho selectivity. Experimentally, reactions employing B2eg2 gave ortho selectivities > 99%. Adding triethylamine significantly improved conversions. This ligand-substrate electrostatic interaction provides a unique control element for selective C-H functionalization.