7005-72-3

Basic information

• Product Name: 4-Chlorodiphenyl ether
• Synonyms: 1-chloro-4-phenoxy-benzen;4-chlorophenoxybenzene;4-monochlorodiphenyloxide;chlorodiphenylether;Ether, p-chlorophenyl phenyl;ether,p-chlorophenylphenyl;monochlorodiphenyloxide;p-Chlorodiphenyl oxide
• CAS NO: 7005-72-3
• Molecular Formula: C₁₂H₉ClO
• Molecular Weight: 204.65
• EINECS: 230-281-7
• Product Categories: Biphenyl & Diphenyl ether
• Mol File: 7005-72-3.mol
• Article Data: 98

Chemical Properties

• Melting Point: -8 °C
• Boiling Point: 161-162 °C19 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.193 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.7 x 10-3 mmHg at 25 °C (calculated, Branson, 1977)
• Refractive Index: n20/D 1.587(lit.)
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: 3.3 mg/L at 25 °C (Branson, 1977)
• Water Solubility: 3.3 mg/L (25 ºC)
• CAS DataBase Reference: 4-Chlorodiphenyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorodiphenyl ether(7005-72-3)
• EPA Substance Registry System: 4-Chlorodiphenyl ether(7005-72-3)

Safety Data

• Hazard Codes: N-Xi,F,N,Xi,Xn
• Statements: 50/53-36/37/38-41-22-43
• Safety Statements: 61-37/39-29-26-60-36/37/39
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 3
• TSCA: T
• Hazardous Substances Data: 7005-72-3(Hazardous Substances Data)

Usage

Description

4-Chlorodiphenyl ether is an organic compound with the chemical formula C12H7ClO, featuring a chlorine atom attached to a diphenyl ether structure. It is a colorless crystalline solid that is relatively stable and insoluble in water.

Uses

Used in Environmental Testing and Research:
4-Chlorodiphenyl ether is used as a standard for environmental testing and research, particularly in the assessment of biodegradability studies with organic priority pollutant compounds. Its stability and solubility properties make it suitable for such applications.
Used in Chemical Synthesis:
4-Chlorodiphenyl ether is used in the preparation of 4′-chloro-2,2′,3,3′,4,5,5′,6,6′-nonabromodiphenyl ether (Cl-BDE-208), which serves as an internal standard in the analysis of highly brominated diphenyl ethers. This application is crucial for accurate quantification and monitoring of these compounds in various environmental and industrial samples.

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 391, 1992 DOI: 10.1021/jo00027a071

Air & Water Reactions

Insoluble or slightly soluble in water.

Reactivity Profile

4-Chlorodiphenyl ether oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164].

Fire Hazard

Combustible.

Environmental fate

Biological. 4-Chlorophenyl phenyl ether (5 and 10 mg/L) did not significantly biodegrade following incubation in settled domestic wastewater inoculum at 25 °C. Percent losses reached a maximum after 2–3 wk but decreased thereafter suggesting a deadaptive process was occurring (Tabak et al., 1981). In activated sludge, a half-life of 4.0 h was measured (Branson, 1978). Photolytic. In a methanolic solution irradiated with UV light (λ >290 nm), dechlorination of 4- chlorophenyl phenyl ether resulted in the formation of diphenyl ether (Choudhry et al., 1977). Photolysis of an aqueous solution containing 10% acetonitrile with UV light (λ = 230–400 nm) yielded 4-hydroxybiphenyl ether and chloride ion (Dulin et al., 1986). At influent concentrations of 1.0, 0.1, 0.01, and 0.001 mg/L, the GAC adsorption capacities were 111, 61, 33, and 18 mg/g, respectively (Dobbs and Cohen, 1980).

InChI:InChI=1/C12H9Cl.C4H10O/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10;1-3-5-4-2/h1-9H;3-4H2,1-2H3

Upstream product

• 106-39-8 bromochlorobenzene 
• 100-67-4 potassium phenolate 
• 101-84-8 diphenylether 
• 1121-74-0 potassium 4-chlorophenoxide 
• 108-86-1 bromobenzene 
• 1193-00-6 sodium 4-chlorophenolate 
• 106-46-7 para-dichlorobenzene 
• 623-12-1 4-chloromethoxybenzene 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 2444-89-5 4,4'-dichlorodiphenyl ether 
• 696-62-8 para-iodoanisole 
• 620-88-2 4-nitrophenyl phenyl ether 
• 56-23-5 tetrachloromethane 
• 7553-56-2 iodine 

Downstream Products

• 69199-63-9 5-chloro-2-phenoxy-benzoic acid 
• 5753-33-3 RB₂₀₂ 
• 10230-34-9 2-Chlor-phenoxathiin 
• 2444-89-5 4,4'-dichlorodiphenyl ether 
• 1836-74-4 4-(4-chlorophenoxy)nitrobenzene 
• 10265-98-2 (4-chloro-3-nitro-phenyl)-phenyl ether 
• 6842-61-1 3-(4-chlorophenoxy)phenyl bromide 
• 30427-95-3 1-bromo-4-(4-chlorophenoxy)benzene 
• 854259-78-2 (3-bromo-4-chloro-phenyl)-phenyl ether 
• 854257-01-5 1-chloro-4-(4-iodophenoxy)benzene 
• 41150-48-5 1-[4-(4-chlorophenoxy)phenyl]ethanone 
• 57148-29-5 3-<4-(4-chlorophenoxy)benzoyl>propionic acid 
• 57148-40-0 4-<4-(4-chlorophenoxy)benzoyl>butyric acid 
• 106364-45-8 2-(4-phenoxyphenyl)propanenitrile 

Relevant articles and documents

Magnetization of graphene oxide nanosheets using nickel magnetic nanoparticles as a novel support for the fabrication of copper as a practical, selective, and reusable nanocatalyst in C-C and C-O coupling reactions

Catalyst species are an important class of materials in chemistry, industry, medicine, and biotechnology. Moreover, waste recycling is an important process in green chemistry and is economically efficient. Herein, magnetic graphene oxide was synthesized using nickel magnetic nanoparticles and further applied as a novel support for the fabrication of a copper catalyst. The catalytic activity of supported copper on magnetic graphene oxide (Cu-ninhydrin@GO-Ni MNPs) was investigated as a selective, practical, and reusable nanocatalyst in the synthesis of diaryl ethers and biphenyls. Some of the obtained products were identified by NMR spectroscopy. This nanocatalyst has been characterized by atomic absorption spectroscopy (AAS), scanning electron microscopy (SEM), wavelength dispersive X-ray spectroscopy (WDX), energy-dispersive X-ray spectroscopy (EDS), X-ray diffraction (XRD), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FT-IR), and vibrating sample magnetometer (VSM) techniques. The results obtained from SEM shown that this catalyst has a nanosheet structure. Also, XRD and FT-IR analysis show that the structure of graphene oxide and nickel magnetic nanoparticles is stable during the modification of the nanoparticles and synthesis of the catalyst. The VSM curve of the catalyst shows that this catalyst can be recovered using an external magnet; therefore, it can be reused several times without a significant loss of its catalytic efficiency. The heterogeneity and stability of this nanocatalyst during organic reactions was confirmed by the hot filtration test and AAS technique.

Synergistic effect of copper nanocrystals-nanoparticles incorporated in a porous organic polymer for the Ullmann C-O coupling r–eaction

A quinoxaline-based porous organic polymer (Q-POP) as a mesoporous organic copolymer was developed as a new platform for the immobilization of CuNPs and copper nanocrystals. The prepared materials were characterized by FT-IR, XRD, N2 adsorption-desorption isotherms, ICP, TGA, SEM, HR-TEM, EDX, and single-crystal X-ray crystallography. The obtained catalyst presented extraordinary catalytic activity towards Ullmann C–O coupling reactions with high surface area, hierarchical porosity, and excellent thermal and chemical stability. Due to its high porosity, and synergistic effect of copper nanocrystals incorporated in the polymer composite, the as-synthesized catalyst was successfully utilized for the Ullmann C–O coupling reaction of phenols and different aryl halides to prepare various diaryl ether derivatives. All types of aryl halides (except aryl fluorides) were screened in the Ullmann C–O coupling reaction with phenols to produce diaryl ethers in good to excellent yields (70–97 %), and it was found that aryl iodides have the best results. Besides, due to the strong interactions between CuNPs, N, and O-atoms of quinoxaline moiety existing in the polymeric framework, the copper leaching from the support was not observed. Furthermore, the catalyst was recycled and reused for five consecutive runs without significant activity loss.

Diaza crown-type macromocycle (kryptofix 22) functionalised carbon nanotube for efficient Ni2+ loading; A unique catalyst for cross-coupling reactions

Raising the capability of supporting and suppressing the leaching possibility to a very insignificant level has still remained challenging for some class of transition metals, i.e. Ni2+. Here we present the covalent functionalisation of macrocyclic ligand, 4,13-diaza-18-crown-6 (kryptofix 22), on the surface of carbon nanotube (CNT), leading to a unique adsorptive capability for supporting Ni2+. This material was incorporated as a promising catalyst in coupling reactions including C[sbnd]C, CN, and CO[sbnd][sbnd] cross-coupling reactions. We demonstrate that the kryptofix 22 functionalisation on the surface of CNT has a key role in the enhancement of the adsorption capability Ni2+ and subsequent catalytic activity. We further prove that this ligand causes a significant boost in the recyclability of the reactions due to the extremely trivial Ni2+ leaching from the CNT's surface during the reactions.