1993-03-9

Basic information

• Product Name: 2-Fluorophenylboronic acid
• Synonyms: 2-Fluorophenylboronic acid, May contain varying amounts of anhydride, 97%;2-Fluorophenylboroni;2-Fluorophenylboronic acid, 98% 1GR;2-Flurorphenylboronic acid;Boronic acid, B-(2-fluorophenyl)-;o-Fluorphenylborsaeure;o-fluoro-benzeneboronic acid;2-Fluorobenzeneboronic Acid (Contains Varying Amounts Of Anhydride)
• CAS NO: 1993-03-9
• Molecular Formula: C₆H₆BFO₂
• Molecular Weight: 139.92
• EINECS: -0
• Product Categories: Boronate Ester;Potassium Trifluoroborate;blocks;BoronicAcids;FluoroCompounds;Substituted Boronic Acids;Heterocyclic Compounds;Boronic Acid;Aryl;Fluorinated;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids;Boronic Acids and Derivatives
• Mol File: 1993-03-9.mol

Chemical Properties

• Melting Point: 101-110 °C(lit.)
• Boiling Point: 267.8 °C at 760 mmHg
• Flash Point: 115.8 °C
• Appearance: White to light yellow/Crystalline Powder
• Density: 1.24 g/cm³
• Vapor Pressure: 0.00395mmHg at 25°C
• Refractive Index: 1.508
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• PKA: 8.32±0.58(Predicted)
• BRN: 3030413
• CAS DataBase Reference: 2-Fluorophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluorophenylboronic acid(1993-03-9)
• EPA Substance Registry System: 2-Fluorophenylboronic acid(1993-03-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-36/37/39-27-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1993-03-9(Hazardous Substances Data)

Usage

Uses

Used in Suzuki Reaction:
2-Fluorophenylboronic acid is used as a reagent in the Suzuki reaction for the formation of carbon-carbon bonds, which is a widely employed method in organic synthesis for creating biaryl compounds.
Used in Rh-Catalyzed Enantioselective Addition Reactions:
2-Fluorophenylboronic acid is used as a reagent in Rhodium-catalyzed enantioselective addition reactions, which are crucial for the synthesis of chiral molecules with a single enantiomer, important in the pharmaceutical industry for producing enantiomerically pure drugs.
Used in Rhodium and Palladium-Catalyzed Substitution Reactions:
2-Fluorophenylboronic acid is utilized as a reagent in Rhodium and Palladium-catalyzed substitution reactions, which are vital for the functionalization of organic molecules and the synthesis of complex organic compounds.
Used in the Preparation of Phenylboronic Catechol Esters:
2-Fluorophenylboronic acid is used as a starting material for the preparation of phenylboronic catechol esters, which are promising anion receptors for polymer electrolytes, finding applications in the development of advanced materials for energy storage and conversion.
Used for the Preparation of Biologically Active Biphenyls:
2-Fluorophenylboronic acid is used as a key intermediate in the synthesis of biologically active biphenyls, which have potential applications in the pharmaceutical industry as drug candidates.
Used for the Preparation of Arylboron Difluoride Lewis Acids:
2-Fluorophenylboronic acid is employed in the preparation of arylboron difluoride Lewis acids, which are valuable catalysts in various organic reactions, including carbon-carbon bond formation and oxidation reactions.

InChI:InChI=1/C6H6BFO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H

Upstream product

• 348-52-7 1-Fluoro-2-iodobenzene 
• 1072-85-1 o-fluorobromobenzene 
• 109-72-8 n-butyllithium 
• 5419-55-6 Triisopropyl borate 
• 462-06-6 fluorobenzene 
• 348-54-9 2-Fluoroaniline 
• 13675-18-8 tetrahydroxydiboron 
• 446-46-8 2-fluorobenzenediazonium tetrafluoroborate 
• 121-43-7 Trimethyl borate 
• 876062-39-4 2-(2-fluorophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 7732-18-5 water 

Downstream Products

• 146140-96-7 2,2-dimethyl-N-(4-(2-fluorophenyl)-3-pyridyl)propanamide 
• 174575-21-4 (2S,5S)-2-tert-Butyl-5-[5-(diethoxy-phosphorylmethyl)-2'-fluoro-biphenyl-3-ylmethyl]-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester 
• 174575-26-9 (2S,5S)-5-[4-Acetoxy-5-(diethoxy-phosphorylmethyl)-2'-fluoro-biphenyl-3-ylmethyl]-2-tert-butyl-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester 
• 299966-25-9 8-methoxy-5-nitro-4-(2'-fluorophenyl)quinoline 
• 584-74-7 o-fluorophenylacetic acid ethyl ester 
• 388-82-9 2,2'-difluorobiphenyl 

Relevant articles and documents

Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis

The kinetics and mechanism of the base-catalyzed hydrolysis (ArB(OR)2→ ArB(OH)2) and protodeboronation (ArB(OR)2→ ArH) of a series of boronic esters, encompassing eight different polyols and 10 polyfluoroaryl and heteroaryl moieties, have been investigated by in situ and stopped-flow NMR spectroscopy (19F,1H, and11B), pH-rate dependence, isotope entrainment,2H KIEs, and KS-DFT computations. The study reveals the phenomenological stability of boronic esters under basic aqueous-organic conditions to be highly nuanced. In contrast to common assumption, esterification does not necessarily impart greater stability compared to the corresponding boronic acid. Moreover, hydrolysis of the ester to the boronic acid can be a dominant component of the overall protodeboronation process, augmented by self-, auto-, and oxidative (phenolic) catalysis when the pH is close to the pKaof the boronic acid/ester.

Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure

The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.

Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation

A new click bioorthogonal reaction system was devised to enable the fast ligation (kON≈340 m-1 s-1) of conjugatable derivatives of a rigid cyclic diol (nopoldiol) and a carefully optimized boronic acid partner, 2-methyl-5-carboxymethylphenylboronic acid. Using NMR and fluorescence spectroscopy studies, the corresponding boronates were found to form reversibly within minutes at low micromolar concentration in water, providing submicromolar equilibrium constant (Keq≈105-106 m-1). Efficient protein conjugation under physiological conditions was demonstrated with model proteins thioredoxin and albumin, and characterized by mass spectrometry and gel electrophoresis.

Preparation method of benzochromene derivative

The invention discloses a preparation method of a benzochromene derivative shown as a formula (I). The benzochromene derivative can be taken as a synthesis intermediate of a drug such as a synthesis intermediate of Velpatasvir. Cheap and available 2-fluoro halogenated benzene is taken as a starting material, a brand-new synthetic route for preparing the benzochromene derivative is provided, the total yield of the whole reaction route is high, and the method is suitable for large-scale industrial production.

Flow Chemistry on Multigram Scale: Continuous Synthesis of Boronic Acids within 1 s

The benefits and limitations of a simple continuous flow setup for handling and performing of organolithium chemistry on the multigram scale is described. The developed metalation platform embodies a valuable complement to existing methodologies, as it combines the benefits of Flash Chemistry (chemical synthesis on a time scale of 1 s) with remarkable throughput (g/min) while mitigating the risk of blockages.

Transition-metal-free synthesis of phenanthridinones from biaryl-2-oxamic acid under radical conditions

Na2S2O8-promoted decarboxylative cyclization of biaryl-2-oxamic acid for phenanthridinones has been developed. This work illustrates the first example of intramolecular decarboxylative amidation of unactivated arene under transition-metal-free conditions. Additionally, this approach provides an efficient and economical method to access biologically interesting phenanthridinones, an important structure motif in many natural products. (Chemical Equation Presented).

An easy route to (hetero)arylboronic acids

An unprecedented spontaneous reactivity between diazonium salts and diboronic acid has been unveiled, leading to a versatile arylboronic acid synthesis directly from (hetero)arylamines. This fast reaction (35 min overall) tolerates a wide range of functional groups and is carried out under very mild conditions. The radical nature of the reaction mechanism has been investigated.

Sequential one-pot access to molecular diversity through aniline aqueous borylation

On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.

Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]

Arylboronic acids are gaining increased importance as reagents and target structures in a variety of useful applications. Recently, the palladium-catalyzed synthesis of arylboronic acids employing the atom-economical tetrahydroxydiboron (BBA) reagent has been reported. The high cost associated with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroaryl halides and pseudohalides using tetrahydroxydiboron (BBA) has been formulated. The reaction proved to be widely functional group tolerant and applicable to a number of heterocyclic systems. To the best of our knowledge, the examples presented here represent the only effective Ni-catalyzed Miyaura borylations conducted at room temperature.

POLYCYCLIC RING-FUSED COMPOUND AND ORGANIC THIN FILM TRANSISTOR UTILIZING SAME

A compound for an organic thin film transistor represented by the following formula (1):