4,4'-Dichlorodiphenyl ether

Base Information

• Chemical Name: 4,4'-Dichlorodiphenyl ether
• CAS No.: 2444-89-5
• Molecular Formula: C12H8 Cl2 O
• Molecular Weight: 239.101
• Hs Code.: 2903999090
• European Community (EC) Number: 674-012-5
• NSC Number: 38001
• UNII: 36VA116FST
• DSSTox Substance ID: DTXSID90179198
• Nikkaji Number: J127.139C
• Wikidata: Q27256589
• Mol file: 2444-89-5.mol

Synonyms:2444-89-5;4-Chlorophenyl ether;4,4'-DICHLORODIPHENYL ETHER;1-Chloro-4-(4-chlorophenoxy)benzene;Bis(p-chlorophenyl) ether;Ether, bis(p-chlorophenyl);p,p'-Dichlorodiphenyl oxide;4,4'-Oxybis(chlorobenzene);4-Chlorophenyl ether,;Benzene, 1,1'-oxybis[4-chloro-;UNII-36VA116FST;36VA116FST;1,1'-oxybis(4-chlorobenzene);NSC 38001;NSC-38001;1,1'-Oxybis[4-chlorobenzene];Benzene, 1,1'-oxybis(4-chloro-;Benzene,1,1'-oxybis[4-chloro-;4-chlorophenylether;Bis(p-chlorophenyl)ether;bis(4-chlorophenyl) ether;PCDE 15;SCHEMBL457634;Benzene,1'-oxybis[4-chloro-;DTXSID90179198;URUJZHZLCCIILC-UHFFFAOYSA-N;Benzene, 1,1'-oxybis*4-chloro-;NSC38001;MFCD00060657;STL268904;AKOS015850267;1-Chloro-4-(4-chlorophenoxy)benzene #;Benzene, 1,1'-oxybis(4-chloro- (9CI);FT-0764183;Q27256589;InChI=1/C12H8Cl2O/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8

Chemical Property of 4,4'-Dichlorodiphenyl ether

Chemical Property:

• Vapor Pressure: 0.00087mmHg at 25°C
• Melting Point: 30 °C
• Refractive Index: 1.6110 (estimate)
• Boiling Point: 312 °C
• Flash Point: 108.8°C
• PSA: 9.23000
• Density: 1.3g/cm³
• LogP: 4.78570
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 237.9952203
• Heavy Atom Count: 15
• Complexity: 162

Purity/Quality:

99%, ^*data from raw suppliers

4,4''-DichlorodiphenylEther ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1OC2=CC=C(C=C2)Cl)Cl

Technology Process of 4,4'-Dichlorodiphenyl ether

There total 28 articles about 4,4'-Dichlorodiphenyl 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: 94.0%

4-chlorophenyl(2,4-dimethoxyphenyl)iodonium tosylate (1428064-54-3) + 4-chloro-phenol (106-48-9,82344-39-6) → 4,4'-dichlorodiphenyl ether (2444-89-5)

Guidance literature:

With potassium carbonate; In acetonitrile; at 50 ℃; for 6h; regioselective reaction;

DOI:10.1055/s-0032-1316824

Reference yield: 94.0%

bromochlorobenzene (106-39-8) + 4-chloro-phenol (106-48-9,82344-39-6) → 4,4'-dichlorodiphenyl ether (2444-89-5)

Guidance literature:

With copper(l) iodide; iron(III)-acetylacetonate; potassium carbonate; In N,N-dimethyl-formamide; at 135 ℃; for 12h; Inert atmosphere;

DOI:10.1055/s-0030-1259291

Reference yield: 93.0%

bis(4-chlorophenyl)iodonium tosylate (59696-06-9) + 4-chloro-phenol (106-48-9,82344-39-6) → 4,4'-dichlorodiphenyl ether (2444-89-5)

Guidance literature:

With potassium carbonate; In acetonitrile; at 50 ℃; for 6h;

DOI:10.1055/s-0032-1316824

upstream raw materials:

diphenylether

4-chlorodiphenyl ether

4-chlorobenzaldehyde

4,4'-oxydiphenylene diamine

Downstream raw materials:

4,4'-dihydroxydiphenyl ether

3,4,4'-Trichlorobiphenyl ether

4-chloro-1-(4-chlorophenoxy)-2-nitrobenzene

4,4'-oxydiphenylene diamine

Refernces

• 1、 Wang, Ying,Li, Lina,Ji, Hongwei,Ma, Wanhong,Chen, Chuncheng,Zhao, Jincai. "Iron(III)-mediated photocatalytic selective substitution of aryl bromine by chlorine with high chloride utilization efficiency". supporting information. p. 2344 - 2346. Retrieved 2014/03/21.
• 2、 Yang, Haitao,Xi, Chao,Miao, Zhiwei,Chen, Ruyu. "Cross-coupling reactions of aryl halides with amines, phenols, and thiols catalyzed by an N,N′-dioxide-copper(I) catalytic system". supporting information; experimental part. p. 3353 - 3360. Retrieved 2011/08/03.