372-18-9

Basic information

• Product Name: 1,3-Difluorobenzene
• Synonyms: 1,3-difluroethylene;Benzene, m-difluoro-;benzene,1,3-difluoro-;Benzene,m-difluoro-;Difluoro-1,3-benzene;m-difluoro-benzen;meta-Difluorobenzene;1,3-DIFLUOROBENZENE
• CAS NO: 372-18-9
• Molecular Formula: C₆H₄F₂
• Molecular Weight: 114.09
• EINECS: 206-746-5
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Fluorobenzene;Fluorine Compounds;Aryl;C6;Halogenated Hydrocarbons;Aryl Fluorinated Building Blocks;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Halogenated Hydrocarbons;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;alkyl Fluorine
• Mol File: 372-18-9.mol
• Article Data: 61

Chemical Properties

• Melting Point: -59 °C
• Boiling Point: 83 °C
• Flash Point: 36 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.163 g/mL at 25 °C(lit.)
• Vapor Pressure: 82.7mmHg at 25°C
• Refractive Index: n20/D 1.438(lit.)
• Storage Temp.: Flammables area
• Solubility: 1.1g/l
• Water Solubility: insoluble
• BRN: 1904537
• CAS DataBase Reference: 1,3-Difluorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Difluorobenzene(372-18-9)
• EPA Substance Registry System: 1,3-Difluorobenzene(372-18-9)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20-2017/11/20
• Safety Statements: 7-16-29-33-7/9
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 1
• RTECS: CZ5652000
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 372-18-9(Hazardous Substances Data)

Usage

Description

1,3-Difluorobenzene is an organic compound with the chemical formula C6H4F2. It is a derivative of benzene, featuring two fluorine atoms attached to the 1,3 positions of the benzene ring. 1,3-Difluorobenzene is known for its unique chemical properties and reactivity, making it a valuable building block in various chemical syntheses.
Used in Pharmaceutical Industry:
1,3-Difluorobenzene is used as a key intermediate in the synthesis of fluorinated pharmaceuticals for its ability to impart specific properties to the final drug molecules. For instance, it is utilized in the production of Fluconazole, an antifungal medication.
Used in Pesticide Industry:
In the agrochemical sector, 1,3-Difluorobenzene serves as a precursor for the development of pesticides such as Flucycloxuron and Diflubenzuron, contributing to the creation of effective pest control agents.
Used in Liquid Crystal Material Synthesis:
1,3-Difluorobenzene is employed in the synthesis of liquid crystal materials, which are crucial for the production of advanced display technologies and other applications that rely on liquid crystal properties.
Used in Scientific Research:
1,3-Difluorobenzene is used in the laser-induced fluorescence matrix study of its radical cation, providing insights into its chemical behavior and potential applications.
Used in the Synthesis of 1,2,3-Triazole Containing Fluconazole Analogues:
1,3-Difluorobenzene is also utilized in the synthesis of 1,2,3-triazole derivatives, which are structurally related to Fluconazole and may exhibit similar or improved pharmaceutical properties.

Synthesis

Higher yields were observed when CsF and HF were reacted with 1,3-dichlorobenzene, which gave I ,3-difluorobenzene.

InChI:InChI=1/C6H4F2/c7-5-2-1-3-6(8)4-5/h1-4H

Upstream product

• 372-19-0 meta-fluoroaniline 
• 75-89-8 2,2,2-trifluoroethanol 
• 1996-38-9 3-fluorobenzenediazonium tetrafluoroborate 
• 367-11-3 ortho-difluorobenzene 
• 540-36-3 para-difluorobenzene 
• 108-90-7 chlorobenzene 
• 71-43-2 benzene 
• 462-06-6 fluorobenzene 
• 352-33-0 1-Chloro-4-fluorobenzene 
• 625-98-9 3-chlorofluorobenzene 
• 348-51-6 1-chloro-2-fluorobenzene 
• 106-46-7 para-dichlorobenzene 
• 149130-47-2 trimethyl(3,5-difluorophenyl)silane 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 

Downstream Products

• 364-83-0 2',4'-difluoroacetophenone 
• 110931-77-6 4-(2,4-difluorophenyl)-4-oxobutanoic acid 
• 139358-54-6 (S)-2-acetoxy-2',4'-difluoropropiophenone 
• 126918-14-7 (2S)-2',4'-Difluoro-2-hydroxypropiophenone 
• 84564-76-1 2-(2,4-Difluorophenyl)propane 
• 83484-00-8 2,6-difluoroisopropylbenzene 
• 126917-43-9 (R)-(2,4-difluorophenyl) 1-chloroethyl ketone 
• 84162-80-1 4-(2,4-difluorobenzoyl)-1-piperidinecarboxaldehyde 
• 372-20-3 3-fluorophenol 
• 461-96-1 3,5-difluorobromobenzene 
• 128259-71-2 1,4 - dibromo-2,6-difluorobenzene 
• 128259-73-4 1,3-Difluoro-1,2,3,4,5,6-hexabromocyclohexane 
• 128259-72-3 2,4,5-Tribromo-1,3-difluorobenzene 
• 46020-63-7 2,4-difluorobenzenesulfonic acid 

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.

Continuous synthesis method of m-difluorobenzene based on micro-channel reactor

The invention discloses a continuous synthesis method of m-difluorobenzene based on a micro-reactor. The continuous synthesis method comprises the following steps: adding m-phenylenediamine and a hydrochloric acid solution into a first micro-channel reactor, and conducting reacting to obtain an m-phenylenediamine hydrochloride solution; subjecting the m-phenylenediamine hydrochloride solution to reacting with nitrogen trioxide in a second micro-channel reactor to prepare a dichlorom-phenylenediamine diazonium salt solution; subjecting the dichlorom-phenylenediamine diazonium salt to reacting with fluoboric acid in a tubular reactor, conducting quick centrifuging after the reaction is finished, washing precipitates obtained by centrifuging, and drying the precipitates to obtain m-phenylenediamine diazonium difluoroborate; and mixing the m-phenylenediamine diazonium difluoroborate with a solvent, adding the obtained mixture into a reactor, carrying out heating for decomposition, carrying out atmospheric distillation on a product in the reactor after the decomposition is finished, and collecting a fraction with a temperature of 82-84 DEG C. According to the invention, nitrogen trioxide is used as a diazotization agent, so the reaction is green, and no by-product is produced; and centrifugal mother liquor in the reaction process is concentrated and then recycled, so cost is saved, and reaction efficiency is high.

Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

This report details a decarboxylative cross-coupling of (hetero)aryl carboxylates with iodoarenes in the presence of a gold catalyst (>25 examples, up to 96% yield). This reaction is site specific, which overcomes prior limitations associated with gold catalyzed oxidative coupling reactions. The reactivity of the (hetero)aryl carboxylate correlates qualitatively to the field effect parameter (Fortho). Reactions with isolated gold complexes and DFT calculations support a mechanism proceeding through oxidative addition at a gold(I) cation with decarboxylation being viable at either a gold(I) or a silver(I) species.