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

Chemical Properties

colorless to light yellow liquid

Uses

Different sources of media describe the Uses of 7005-72-3 differently. You can refer to the following data:
1. 4-Chlorodiphenyl Ether is a standard for environmental testing and research. Biodegradability studies with organic priority pollutant compounds.
2. 4-Chlorodiphenyl ether can be used in the preparation of 4′-chloro-2,2′,3,3′,4,5,5′,6,6′-nonabromodiphenyl ether (Cl-BDE-208), an internal standard used in the analysis of highly brominated diphenyl ethers.

Synthesis Reference(s)

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

General Description

Liquid. Density 1.193 g / cm3. Insoluble or slightly soluble in water.

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

• 623-12-1 4-chloromethoxybenzene 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 2444-89-5 4,4'-dichlorodiphenyl ether 
• 696-62-8 para-iodoanisole 
• 101-84-8 diphenylether 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 56-23-5 tetrachloromethane 
• 108-86-1 bromobenzene 
• 1121-74-0 potassium 4-chlorophenoxide 
• 108-95-2 phenol 
• 591-50-4 iodobenzene 
• 106-48-9 4-chloro-phenol 
• 106-46-7 para-dichlorobenzene 

Downstream Products

• 69199-63-9 5-chloro-2-phenoxy-benzoic acid 
• 101973-95-9 2-methylene-3-<4-(4-chlorophenoxy)benzoyl>propionic acid 
• 13221-80-2 2-chloro-1-[4-(4-chlorophenoxy)phenyl]ethanone 
• 10230-34-9 2-Chlor-phenoxathiin 
• 6842-61-1 3-(4-chlorophenoxy)phenyl bromide 
• 30427-95-3 1-bromo-4-(4-chlorophenoxy)benzene 
• 854257-01-5 1-chloro-4-(4-iodophenoxy)benzene 
• 2444-89-5 4,4'-dichlorodiphenyl ether 
• 63646-51-5 3,4,4'-Trichlorobiphenyl ether 
• 55538-69-7 1,2-dichloro-4-phenoxybenzene 
• 1836-74-4 4-(4-chlorophenoxy)nitrobenzene 
• 10265-98-2 (4-chloro-3-nitro-phenyl)-phenyl ether 
• 106-48-9 4-chloro-phenol 
• 108-95-2 phenol 

Relevant articles and documents

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.

Copper nanoparticle anchored biguanidine-modified Zr-UiO-66 MOFs: a competent heterogeneous and reusable nanocatalyst in Buchwald-Hartwig and Ullmann type coupling reactions

We have designed a functionalized metal-organic framework (MOF) of UiO topology as a support, with an extremely high surface area, adjustable pore sizes and stable crystalline coordination polymeric structure and implanted copper (Cu) nanoparticles thereon. The core three dimensional Zr-derived MOF (UiO-66-NH2) was modified with a biguanidine moiety following a covalent post-functionalization approach. The morphological and physicochemical features of the material were determined using analytical methods such as FT-IR, SEM, TEM, EDX, atomic mapping, XRD and ICP-OES. The SEM and XRD results justified the unaffected morphology of Zr-MOF after structural modifications. The as-synthesized UiO-66-biguanidine/Cu nanocomposite was catalytically explored in the aryl and heteroaryl Buchwald-Hartwig C-N and Ullmann type C-O cross coupling reactions with excellent yields. A library of biaryl amine and biaryl ethers was synthesized over the catalyst under mild and green conditions. Furthermore, the catalyst was isolated by centrifugation and recycled 11 times with no significant copper leaching or change in its activity.

Oxidative Photochlorination of Electron-Rich Arenes via in situ Bromination

Electron-rich arenes are oxidatively photochlorinated in the presence of catalytic amounts of bromide ions, visible light, and 4CzIPN as organic photoredox catalyst. The substrates are brominated in situ in a first photoredox-catalyzed oxidation step, followed by a photocatalyzed ipso-chlorination, yielding the target compounds in high ortho/para regioselectivity. Dioxygen serves as a green and convenient terminal oxidant. The use of aqueous hydrochloric acid as the chloride source reduces the amount of saline by-products.