625-98-9

Usage

Chemical Properties

Clear colourless to light yellow liquid

Uses

1-Chloro-3-fluorobenzene used as medicine and liquid crystal intermediates.

General Description

Reaction of 1-chloro-3-fluorobenzene radical cation with NH3 has been investigated by FT-ICR spectrometry. It reacts with n-butyllithium to yield bicycloadducts via trapping of intermediate benzynes.

InChI:InChI=1/C6H4ClF/c7-5-2-1-3-6(8)4-5/h1-4H

Upstream product

• 387-45-1 2-chloro-6-fluorobenzaldehyde 
• 121-73-3 3-Nitrochlorobenzene 
• 36556-50-0 2,3-dichlorofluorobenzene 
• 697-14-3 2-chloro-2,3,3-trifluoro-1-vinylcyclobutane 
• 108-90-7 chlorobenzene 
• 108-42-9 3-chloro-aniline 
• 541-73-1 1,3-Dichlorobenzene 
• 1073-06-9 3-fluorobromobenzene 
• 56-23-5 tetrachloromethane 
• 462-06-6 fluorobenzene 
• 7790-99-0 Iodine monochloride 
• 57946-56-2 2-fluoro-4-chloroaniline 
• 75-89-8 2,2,2-trifluoroethanol 
• 456-39-3 3-chlorobenzenediazonium tetrafluoroborate 

Downstream Products

• 372-19-0 meta-fluoroaniline 
• 327-91-3 2-fluoro-4-chloro-1,3,5-trinitrobenzene 
• 2106-50-5 2-chloro-4-fluoro-1-nitrobenzene 
• 782-60-5 6-Fluor-4-chlor-benzol-disulfonsaeure-(1,3)-dichlorid 
• 133117-45-0 1-chloro-2-trimethylsilyl-3-fluorobenzene 
• 396-64-5 3,3'-difluoro-biphenyl 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 72093-48-2 4-methoxy-3'-fluorobiphenyl 
• 112611-90-2 2-Chloro-4-fluoro-1-isopropyl-benzene 
• 112611-89-9 4-Chloro-2-fluoro-1-isopropyl-benzene 
• 99237-13-5 1-Chloro-3-fluoro-2-isopropyl-benzene 
• 605-39-0 2,2'-dimethyl-1,1'-biphenyl 
• 80254-70-2 3'-Fluoro-2-methyl-biphenyl 
• 403-54-3 m-Fluorobenzonitrile 

Relevant academic research and scientific papers

Fluorination of arylboronic esters enabled by bismuth redox catalysis

Bismuth catalysis has traditionally relied on the Lewis acidic properties of the element in a fixed oxidation state. In this paper, we report a series of bismuth complexes that can undergo oxidative addition, reductive elimination, and transmetallation in a manner akin to transition metals. Rational ligand optimization featuring a sulfoximine moiety produced an active catalyst for the fluorination of aryl boronic esters through a bismuth (III)/bismuth (V) redox cycle. Crystallographic characterization of the different bismuth species involved, together with a mechanistic investigation of the carbonfluorine bond-forming event, identified the crucial features that were combined to implement the full catalytic cycle.

Hydro/deutero deamination of arylazo sulfones under metal and (photo)catalyst-free conditions

Hydrodeaminated and monodeuterated aromatics were obtained via a visible-light driven reaction of arylazo sulfones. Deuteration occurs efficiently in deuterated media such as isopropanol-d8 or in THF-d8/water mixtures and exhibits a high tolerance to the nature and the position of the aromatic substituents.

Mechanochemical Activation of Zinc and Application to Negishi Cross-Coupling

A form independent activation of zinc, concomitant generation of organozinc species and engagement in a Negishi cross-coupling reaction via mechanochemical methods is reported. The reported method exhibits a broad substrate scope for both C(sp3)–C(sp2) and C(sp2)–C(sp2) couplings and is tolerant to many important functional groups. The method may offer broad reaching opportunities for the in situ generation organometallic compounds from base metals and their concomitant engagement in synthetic reactions via mechanochemical methods.

PROCESS FOR THE PREPARATION OF ORGANIC HALIDES

The present invention provides a halo-de-carboxylation process for the preparation of organic chlorides, organic bromides and mixtures thereof, from their corresponding carboxylic acids, using a chlorinating agent selected from trichloroisocyanuric acid (TCCA), dichloroisocyanuric acid (DCCA), or combination thereof, and a brominating agent.

METHOD FOR AROMATIC FLUORINATION

Disclosed is a fluorination method comprising providing an aryl fluorosuifonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosuifonate and the fluorinating reagent to provide a fluorinated aryl species. Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxyiate, and SO2F2 to a reaction mixture; reacting the SO2F2 and the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar-OH to a reaction mixture; where A is an aryl or heteroaryl; providing SO2F2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO2F2, the fluorinating reagent and the compound having the structure Ar-OH to provide a fluorinated aryl species having the structure Ar-F.

Nucleophilic deoxyfluorination of phenols via aryl fluorosulfonate intermediates

This report describes a method for the deoxyfluorination of phenols with sulfuryl fluoride (SO2F2) and tetramethylammonium fluoride (NMe4F) via aryl fluorosulfonate (ArOFs) intermediates. We first demonstrate that the reaction of ArOFs with NMe4F proceeds under mild conditions (often at room temperature) to afford a broad range of electronically diverse and functional group-rich aryl fluoride products. This transformation was then translated to a one-pot conversion of phenols to aryl fluorides using the combination of SO2F2 and NMe4F. Ab initio calculations suggest that carbon-fluorine bond formation proceeds via a concerted transition state rather than a discrete Meisenheimer intermediate.

Reactions of aromatic compounds with xenon difluoride

Reactions of substituted benzenes C6H5R (R = Me, F, Cl, Br, CF3, NO2) with xenon difluoride in the presence of boron trifluoride–diethyl ether complex in weakly acidic (1,1,1,3,3-pentafluorobutane) and weakly basic media (acetonitrile) have been studied. These reactions lead to the formation of fluorobenzene derivatives FC6H4R (isomer mixture) together with isomeric difluorobenzenes and fluorinated and non-fluorinated biphenyls. The results have been compared with previously reported data obtained in other solvents using other catalysts.

Fluorination of aromatic compounds with xenon difluoride in the presence of boron trifluoride etherate

Fluorination of benzene with the XeF2 - BF3?Et2O system in acetonitrile at low temperatures affords fluorobenzene in 18% yield, the conversion of benzene being 92%. The rest products are di-, tri-, tetra-, and polyphenyls with different fluorination pattern. Toluene and chloro- and bromobenzenes are fluorinated predominantly at the ortho and para positions. Fluorination of 4-nitroanisole affords 2-fluoro-4-nitroanisole in 73% yield.

Protodecarboxylation of carboxylic acids over heterogeneous silver catalysts

A heterogeneous supported Ag catalyst for the protodecarboxylation of aromatic carboxylic acids has been developed. Control of the metal particle size proved extremely important. The highest activity was achieved with a silver loading of 10 wt%, which had relatively big metal crystallites of 40 nm. It is inferred that the adsorption of the aromatic moiety requires terrace sites rather than edges or corners at the metal nanoparticle. The amphoteric support, γ-Al2O3, gave the most active catalysts. Oxygen coverage of the surface is essential for catalytic activity. A mechanism has been proposed with the critical steps (1) formation of a benzoyl anion by reaction with a base in the reaction medium, (2) binding of the anionic species at the Ag+ surface sites with (3) extrusion of CO2 and (4) proton transfer from another molecule of carboxylic acid, followed by desorption of the decarboxylated species and binding of the benzoate to the active site to complete the catalytic cycle. With 2-nitrobenzoic acid as substrate, the catalyst had a turnover frequency (TOF) of 216 h-1. The catalyst showed good activity for benzoic acid with nitro, methoxy and halogen substituents at the ortho-position as well as for heteroaromatic carboxylic acids. The Royal Society of Chemistry.

Direct trifluoro-methoxylation of aromatics with perfluoro-methyl- hypofluorite

The reactivity of CF3OF (FTM) has been widely studied especially in halogenated olefinic systems and its use in pharmaceutical synthesis as a mild radical and electrophilic fluorinating agent is well documented. On the other hand, the chemical behavior of the perfluoro-methyl-hypofluorite with aromatic substrates is much less studied. Up to now few and scattered data regarding its use as electrophilic fluorinating agent of variously substituted aromatic compounds are found in the literature. In this work the reactivity of CF3OF with simple electron rich and electron poor aromatics (α,α,α-trifluoro-toluene, toluene, benzene, chloro-benzene, methoxybenzene) has been investigated. The possibility of selectively bind the trifluoro-methoxy group (via radical mechanism) or the fluorine atom (via electrophilic addition) by varying the reaction conditions has been explored. In particular we have observed that the trifluoro-methoxy free radical substitution can be the main synthetic pathway if the reaction is promoted by an independent and steady source of CF3O radical.