51230-49-0

Basic information

• Product Name: 2-CHLORODIBENZOFURAN
• Synonyms: 2-chloro-dibenzofura;2-chlorodibenzofuran;2-mcdf;monochlorodibenzofuran;2-CHLORODIBENZOFURAN (50 UG/ML IN ISOOCTANE);2-CDF;PCDF 2;2-chlorodibenzo[b,d]furan
• CAS NO: 51230-49-0
• Molecular Formula: C₁₂H₇ClO
• Molecular Weight: 202.63638
• Mol File: 51230-49-0.mol

Chemical Properties

• Melting Point: 100℃
• Boiling Point: 310.96°C (rough estimate)
• Flash Point: 149.1 °C
• Appearance: /
• Density: 1.2600 (estimate)
• Vapor Pressure: 0.000509mmHg at 25°C
• Refractive Index: 1.7100 (rough estimate)
• CAS DataBase Reference: 2-CHLORODIBENZOFURAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORODIBENZOFURAN(51230-49-0)
• EPA Substance Registry System: 2-CHLORODIBENZOFURAN(51230-49-0)

Safety Data

• Hazardous Substances Data: 51230-49-0(Hazardous Substances Data)

Usage

Uses

Used in Environmental Testing and Research:
2-Chlorodibenzofuran is used as a standard reference material for environmental testing and research. It plays a crucial role in studying the formation of dibenzofurans and dibenzodioxins, which are toxic compounds that can be released from waste incinerators and fly ash. The presence of 2-Chlorodibenzofuran in these studies helps to understand the formation mechanisms, environmental impact, and potential health risks associated with these toxic compounds.

InChI:InChI=1/C12H7ClO/c13-8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h1-7H

Upstream product

• 132-64-9 dibenzofuran 
• 93-67-4 5-chloro-2-phenoxyaniline 
• 2770-11-8 2-(4-chlorophenoxy)aniline 
• 86-77-1 2-hydroxydibenzofuran 
• 144463-67-2 allyl 2-(4-chlorophenoxy)benzoate 
• 2051-61-8 m-chlorobiphenyl 
• 3693-22-9 dibenzo[b,d]furan-2-amine 
• 106-48-9 4-chloro-phenol 
• 120-83-2 2,4-dichlorophenol 
• 108-95-2 phenol 
• 87-86-5 Pentachlorophenol 
• 583-78-8 2,5-dichlorophenol 
• 933-78-8 2,3,5-trichlorophenol 
• 58-90-2 2,3,4,6-tetrachlorophenol 

Downstream Products

• 51596-37-3 2-chloro-7-nitro-dibenzofuran 
• 132-64-9 dibenzofuran 
• 103264-74-0 1,4-dihydro-dibenzofuran 
• 90-43-7 2-Phenylphenol 
• 2786-05-2 dibenzofuran-4-carboxylic acid 
• 19261-06-4 4-hydroxydibenzofuran 
• 947770-80-1 4,4,5,5-tetramethyl-2-{8-oxatricyclo[7.4.0²,⁷,]trideca-1⁽⁹⁾,2,4,6,10,12-hexaen-4-yl}-1,3,2-dioxaborolane 

Relevant articles and documents

In Situ Formed IIII-Based Reagent for the Electrophilic ortho-Chlorination of Phenols and Phenol Ethers: The Use of PIFA-AlCl3 System

A new and in situ formed reagent generated by mixing PIFA {bis[(trifluoroacetoxy)iodobenzene]} and AlCl3 was introduced in the organic synthesis for the direct and highly regioselective ortho-chlorination of phenols and phenol ethers. An efficient electrophilic chlorination for these electron-rich arenes as well as the scope of the reaction are described herein. An easy, practical, and open-flask reaction allowed us to introduce a chlorine atom, which is a highly important functional group in organic synthesis. The reproducibility of our method has been demonstrated on gram-scale by carrying out the reaction in 6-bromo-2-naphthol. This halogenation reaction also proceeds in excellent conditions by first preparing the iodine(III)-based chlorinating reagent. Our new chlorinating reagent can be stored at least for two weeks at 4 °C without losing its reactivity.

Visible-Light-Promoted Synthesis of Dibenzofuran Derivatives

Dibenzofurans are naturally occurring molecules that have received considerable attention for a variety of practical applications, such as in pharmaceuticals and electronic materials. Herein, an efficient and eco-friendly method for the synthesis of dibenzofuran derivatives via intramolecular C-O bond formation, which involves the in situ production of a diazonium salt, is described. The transformation requires a diazotizing agent and is promoted by the use of an organic photosensitizer under visible-light irradiation.

Palladium-catalyzed intra-and intermolecular C-H arylation using mesylates: Synthetic scope and mechanistic studies

This paper describes the development of Pd-catalyzed inter-and intramolecular direct arylation using mesylates. Furthermore, a sequential mesylation/arylation protocol using phenols as substrates is described. These transformations are general with respect to the electronics of the C-H substrates and allow for the synthesis of diverse heterocyclic motifs in good yields. Both arenes and heteroarenes efficiently participate in these reactions. Preliminary mechanistic studies are presented for both inter-and intramolecular arylations.

Rhodium-catalyzed decarbonylative C-H arylation of 2-aryloxybenzoic acids leading to dibenzofuran derivatives

Rhodium-catalyzed intramolecular C-H arylation of 2-aryloxybenzoic acids proceeded accompanied by decarbonylation to give dibenzofuran derivatives in high yields. The present reaction is widely applicable to substrates bearing various functionalities.

Palladium-catalyzed intramolecular C-H arylation of arenes using tosylates and mesylates as electrophiles

This paper describes a method for the palladium catalyzed intramolecular C-H arylation using tosylates and mesylates as electrophiles. The transformation is efficient for the synthesis of various heterocyclic motifs including furans, carbazoles, indoles, and lactams. Additionally, a protocol for the one-pot sequential tosylation/arylation of phenol derivatives is presented.

Synthesis of dibenzofurans by palladium-catalysed tandem denitrification/C-H activation

A palladium-catalysed method for intramolecular cyclisation of ortho-diazonium salts of diaryl ethers to give dibenzofurans is described. The protocol uses 3 mol% palladium acetate as the catalyst in refluxing ethanol in the absence of base. Georg Thieme Verlag Stuttgart · New York.

Oxidative cyclization of 2-arylphenols to dibenzofurans under Pd(II)/peroxybenzoate catalysis

2-Arylphenols undergo intramolecular C-H bond activation/C-O bond formation to afford dibenzofuran derivatives under palladium catalysis in the presence of tert-butyl peroxybenzoate as an oxidant. Kinetic isotope effect experiments indicated that C-H bond cleavage is the rate-limiting step of the reaction.

Formation of dibenzofurans by flash vacuum pyrolysis of aryl 2-(allyloxy)benzoates and related reactions

Flash vacuum pyrolysis (FVP) of aryl 2-(allyloxy)benzoates 5 and of the corresponding aryl 2-(allylthio)benzoates 6 at 650°C, gives dibenzofurans 19 and dibenzothiophenes 20, respectively. The mechanism involves generation of phenoxyl (or thiophenoxyl) radicals by homolysis of the O-allyl (or S-allyl) bond, followed by ipso attack at the ester group, loss of CO2 and cyclisation of the resulting aryl radical. Synthetically, the procedure works well for p-substituted substrates, which lead to 2-substituted dibenzofurans 19b-f (73-90%) and dibenzothiophenes 20b-c (90-94%). Little selectivity is shown in the cyclisation of m-substituted substrates and competing interactions of the radical with the substituent - and ipso-attack - complicate the pyrolyses of o-substituted substrates. FVP of related radical precursors including 2-(allyloxy)phenyl benzoates 43 gave no dibenzofurans, whereas 2-(allyloxy-5-methyl)azobenzene 44 gave a much reduced yield. No carbazoles were obtained by FVP of 4-methylphenyl 2-(allylamino)benzoate 42.

Prediction of polychlorinated dibenzofuran congener distribution from gas-phase phenol condensation pathways

A model for predicting the distribution of dibenzofuran and polychlorinated dibenzofuran (PCDF) congeners from a distribution of phenols was developed. The model is based on a simplified chemical mechanism. Relative rate constants and reaction order with respect to phenol precursors were derived from experimental results using single phenols and equal molar mixtures of up to four phenols. For validation, experiments were performed at three temperatures using a distribution of phenol and 19 chlorinated phenols as measured in municipal waste incinerator exhaust gas. Comparison of experimental measurements and model predictions for PCDF isomer distributions and homologue pattern shows agreement within measurement uncertainty. The R-squared correlation coefficient exceeds 0.9 for all PCDF isomer distributions and the distribution of PCDF homologues. These results demonstrate that the distribution of dibenzofuran and the 135 PCDF congeners from gas-phase condensation of phenol and chlorinated phenols can be predicted from measurement of the distribution of phenol and the 19 chlorinated phenol congeners.

Identification of surrogate compounds for the emission of PCDD/F (I-TEQ value) and evaluation of their on-line realtime detectability in flue gases of waste incineration plants by REMPI-TOFMS mass spectrometry

Correlations between products of incomplete combustion (PIC), e.g., chloroaromatic compounds, can be used to characterise the emissions from combustion processes, like municipal or hazardous waste incineration. A possible application of such relationships may be the on-line real-time monitoring of a characteristic surrogate, e.g., with Resonance-Enhanced Multiphoton Ionization-Time-of-Flight Mass Spectrometry (REMPI-TOFMS). In this paper, we report the relationships of homologues and individual congeners of chlorinated benzenes (PCBz), dibenzo-p-dioxins (PCDD), dibenzofurans (PCDF) and phenols (PCPh) to the International Toxicity Equivalent (I-TEQ) of the PCDD/F (I-TEQ value) in the flue gas and stack gas of a 22 MW hazardous waste incinerator (HWI). As the REMPI detection sensitivity is decreasing with the increase of the degree of chlorination, this study focuses on the lower chlorinated species of the compounds mentioned above. Lower chlorinated species, e.g., chlorobenzene (MCBz), 1,4-dichlorobenzene, 2,4,6-trichlorodibenzofuran or 2,4-dichlorophenol, were identified as I-TEQ surrogates in the flue gas. In contrast to the higher chlorinated phenols, the lower chlorinated phenols (degree of chlorination 4) were not reliable as surrogates in the stack gas. The identified surrogates are evaluated in terms of their detectability by REMPI-TOFMS laser mass spectrometry. The outcome is that MCBz is the best suited surrogate for (indirect) on-line measuring of the I-TEQ value in the flue gas by REMPI-TOFMS. The correlation coefficient r of the MCBz concentration to the I-TEQ in the flue gas was 0.85.