Diphenyl ether

Base Information

• Chemical Name: Diphenyl ether
• CAS No.: 101-84-8
• Molecular Formula: C12H10O
• Molecular Weight: 170.211
• Hs Code.: 2909.30
• European Community (EC) Number: 202-981-2
• ICSC Number: 0791
• NSC Number: 174083,19311
• UN Number: 3077
• UNII: 3O695R5M1U
• DSSTox Substance ID: DTXSID9021847
• Nikkaji Number: J3.598J
• Wikipedia: Diphenyl ether,Diphenyl_ether
• Wikidata: Q419453
• RXCUI: 2391140
• Metabolomics Workbench ID: 46549
• ChEMBL ID: CHEMBL38934
• Mol file: 101-84-8.mol

Synonyms:diphenyl ether;phenyl ether

Chemical Property of Diphenyl ether

Chemical Property:

• Appearance/Colour: clear pale yellowish liquid after melting
• Vapor Pressure: 0.0223mmHg at 25°C
• Melting Point: 26 °C
• Refractive Index: n20/D 1.579(lit.)
• Boiling Point: 258.3 °C at 760 mmHg
• Flash Point: 99.3 °C
• PSA: 9.23000
• Density: 1.063 g/cm³
• LogP: 3.47890
• Water Solubility.: insoluble
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 170.073164938
• Heavy Atom Count: 13
• Complexity: 116

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): N,Xi,T
• Hazard Codes: Xi:Irritant;; <
• Statements: R36/37/38:; R51/53:
• Safety Statements: S26:; S37/39:; S57:; S60:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C1=CC=C(C=C1)OC2=CC=CC=C2
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes, skin and upper respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis.

Technology Process of Diphenyl ether

There total 291 articles about Diphenyl ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

Hexamethyldisiloxane (107-46-0) + benzenediazonium tetrafluoroborate (369-57-3) → diphenylether (101-84-8) + trimethylsilyl fluoride (420-56-4) + tris(trimethylsilyl)borate (4325-85-3) + phenyltrimethylsilyl ether (1529-17-5)

Guidance literature:

In 1,1,2-Trichloro-1,2,2-trifluoroethane; 1.) 0 to 55 deg C very slowly, 2.) sonication, reflux, 16-17 h;

DOI:10.1055/s-1991-26419

Reference yield: 42.0%

tetraphenyl-bismuth trifluoroacetate (83566-43-2) + phenol (108-95-2,27073-41-2) → diphenylether (101-84-8) + (1,1';3',1''-terphenyl)-2'-ol (2432-11-3) + 2-Phenylphenol (90-43-7,287950-96-3)

Guidance literature:

With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; In toluene; at 80 ℃; for 24h; in the dark;

DOI:10.1016/S0040-4020(01)89960-9

Reference yield: 35.0%

tetraphenylbismuth 4-methylbenzenesulfonate (83566-44-3) + phenol (108-95-2,27073-41-2) → diphenylether (101-84-8) + (1,1';3',1''-terphenyl)-2'-ol (2432-11-3) + 2-Phenylphenol (90-43-7,287950-96-3)

Guidance literature:

With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine;

DOI:10.1016/S0040-4020(01)89960-9

upstream raw materials:

bromobenzene

potassium phenolate

phosphoric acid triphenyl ester

sodium salicylate

Downstream raw materials:

N-phenyl piperidine

Trichloroethylene

4-oxo-4-(4-phenoxyphenyl)butanoic acid

4,4'-oxybis<γ-oxobenzenebutanoic acid>

Refernces

• 1、 Beringer,Gindler. "". . p. 3203. Retrieved 1955.
• 2、 Franco, Ana,De, Sudipta,Balu, Alina M.,Garcia, Araceli,Luque, Rafael. "Mechanochemical synthesis of graphene oxide-supported transition metal catalysts for the oxidation of isoeugenol to vanillin". . p. 1439 - 1445. Retrieved 2017.
• 3、 Sarvestani, Mosayeb,Azadi, Roya. "Buchwald-Hartwig amination reaction of aryl halides using heterogeneous catalyst based on Pd nanoparticles decorated on chitosan functionalized graphene oxide". . . Retrieved 2018.
• 4、 Hardouin Duparc, Valérie,Schaper, Frank. "Sulfonato-diketimine Copper(II) Complexes: Synthesis and Application as Catalysts in Chan-Evans-Lam Couplings". . p. 3053 - 3060. Retrieved 2017.
• 5、 Chen, Chuncheng,Duan, Ran,Meng, Di,Song, Wenjing,Wei, Yan,Zhao, Jincai,Zhen, Shengli,Zhu, Qian. "Light-driven activation of carbon-halogen bonds by readily available amines for photocatalytic hydrodehalogenation". . p. 1474 - 1479. Retrieved 2020.
• 6、 Xu, Li-Wen,Xia, Chun-Gu,Li, Jing-Wei,Hu, Xiao-Xue. "Highly Efficient C-O Cross-Coupling Reactions with Unactivated Halides by Ligandless, Heterogeneous Raney Ni-Al Alloy/Copper (I) Salts". . p. 2071 - 2073. Retrieved 2003.
• 7、 Gujadhur, Rattan K.,Bates, Craig G.,Venkataraman. "Formation of aryl-nitrogen, aryl-oxygen, and aryl-carbon bonds using well-defined copper(I)-based catalysts". . p. 4315 - 4317. Retrieved 2001.
• 8、 Bistri, Olivia,Correa, Arkaitz,Bolm, Carsten. "Iron-catalyzed C-O cross-couplings of phenols with aryl iodides". . p. 586 - 588. Retrieved 2008.
• 9、 Abramovitch,Robson. "-". . p. 1101. Retrieved 1967.
• 10、 Kidwai, Mazaahir,Mishra, Neeraj Kumar,Bansal, Vikas,Kumar, Ajeet,Mozumdar, Subho. "Cu-nanoparticle catalyzed O-arylation of phenols with aryl halides via Ullmann coupling". . p. 8883 - 8887. Retrieved 2007.