4,4'-Dichlorobiphenyl

Base Information

• Chemical Name: 4,4'-Dichlorobiphenyl
• CAS No.: 2050-68-2
• Molecular Formula: C12H8Cl2
• Molecular Weight: 223.102
• Hs Code.: 2903999010
• European Community (EC) Number: 218-095-4
• NSC Number: 1141
• UNII: DOF6S5DT2R
• DSSTox Substance ID: DTXSID0022515
• Nikkaji Number: J7.868I
• Wikidata: Q27116020
• Metabolomics Workbench ID: 54971
• ChEMBL ID: CHEMBL14295
• Mol file: 2050-68-2.mol

Synonyms:4,4'-dichlorobiphenyl;4-DCB cpd

Chemical Property of 4,4'-Dichlorobiphenyl

Chemical Property:

• Melting Point: 288℃
• Refractive Index: 1.5940 (rough estimate)
• Boiling Point: 318 °C at 760 mmHg
• Flash Point: 145.2 °C
• PSA: 0.00000
• Density: 1.249g/cm³
• LogP: 4.66040
• Storage Temp.: 2-8°C
• Water Solubility.: 53ug/L(25 oC)
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 222.0003056
• Heavy Atom Count: 14
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): FXi,Xn
• Hazard Codes: F,Xi,Xn,N
• Statements: 11-36/37/38-22-50/53-33-67-65-38
• Safety Statements: 16-26-33-36-61-60-35-62

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC=C(C=C2)Cl)Cl
• Uses: 4,4''-Dichlorobiphenyl is a polychlorinated biphenyl (PCB) congeners.

Technology Process of 4,4'-Dichlorobiphenyl

There total 251 articles about 4,4'-Dichlorobiphenyl 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: 97.0%

1-Chloro-4-iodobenzene (637-87-6) → 4,4'-dichlorobiphenyl (2050-68-2)

Guidance literature:

With PEG 4000; palladium diacetate; potassium carbonate; at 120 ℃; for 4h;

DOI:10.1021/jo052300a

Reference yield: 96.5%

bromochlorobenzene (106-39-8) + 4-Chlorophenylboronic acid (1679-18-1) → 4,4'-dichlorobiphenyl (2050-68-2)

Guidance literature:

With palladium(II) trifluoroacetate; 4,4'-Dimethoxy-2,2'-bipyridin; trifluoroacetic acid; copper(I) bromide; In 1,4-dioxane; at 20 - 80 ℃; for 4h; Reagent/catalyst; Solvent;

Reference yield: 92.0%

bromochlorobenzene (106-39-8) + C4H12BO4(1+)*K(1+) → 4-chloromethoxybenzene (623-12-1) + 4,4'-dichlorobiphenyl (2050-68-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert-butyl XPhos; In N,N-dimethyl-formamide; at 100 ℃; for 1h; Inert atmosphere;

DOI:10.1002/adsc.201300687

upstream raw materials:

biphenyl

4,4'-Dihydroxybiphenyl

bis(4-chlorobenzoyl)peroxide

4,4'-dichloro-biphenyl-3,3'-dicarboxylic acid

Downstream raw materials:

4,4'-di(phenylthio)-1,1'-biphenyl

4,4'-Dihydroxybiphenyl

4,4'-diphenic acid

4,4’-bis(2-phenylethynyl)-1,1’-biphenyl

Refernces

• 1、 Iranpoor, Nasser,Shekarriz, Marzieh. "Homocoupling of substituted benzenes to symmetrical biaryls with mercury(II) in the presence of cerium(IV)". . p. 442 - 443. Retrieved 1999.
• 2、 Shao, Linjun,Du, Yijun,Zeng, Minfeng,Li, Xiudong,Shen, Wenting,Zuo, Shufeng,Lu, Yueqing,Zhang, Xian-Man,Qi, Chenze. "Ethanol-promoted reductive homocoupling reactions of aryl halides catalyzed by palladium on carbon (Pd/C)". . p. 421 - 425. Retrieved 2010.
• 3、 Gorbunova,Pervova,Saloutin,Chupakhin. "Uncatalyzed Hydrodechlorination of Dichlorobiphenyls". . p. 988 - 990. Retrieved 2019.
• 4、 Boyarskii,Sangaranarayanan,Boyarskaya,Tolstopyatova,Chulkova. "Electrochemical Reduction of Trichlorobiphenyls: Mechanism and Regioselectivity". . . Retrieved 2018.
• 5、 Amaya, Toru,Suzuki, Riyo,Hirao, Toshikazu. "Quinonediimine-induced oxidative coupling of organomagnesium reagents". . p. 653 - 656. Retrieved 2014.
• 6、 Koza, Darrell J.,Carita, Eric. "An efficient high yielding approach for the homocoupling of aryl boronic acids". . p. 2183 - 2186. Retrieved 2002.
• 7、 Singh, Fateh Veer,Stefani, Hélio A.. "Ultrasound-assisted synthesis of symmetrical biaryls by palladium-catalyzed homocoupling of aryl n-butyl tellurides". . p. 3221 - 3225. Retrieved 2008.
• 8、 Wu, Nan,Li, Xinnian,Xu, Xin,Wang, Yumei,Xu, Yunyun,Chen, Xi. "Homocoupling reaction of aryl boronic acids catalyzed by Pd(OAc) 2/ K2CO3 in water under air atmosphere". . p. 11 - 14. Retrieved 2010.
• 9、 Ortgies, Dirk H.,Chen, Fei,Forgione, Pat. "Palladium and TEMPO as co-catalysts in a desulfinative homocoupling reaction". . p. 3917 - 3922. Retrieved 2014.
• 10、 Shishkina, I. N.,Dotsenko, I. A.,Demyanovich, V. M.,Bumagin, N. A.,Zefirov, N. S.. "Palladium-catalyzed reactions of halogen derivatives of N,N-Dimethyl-1-Phenylethanamine with arylboronic acids as a novel approach to the synthesis of biaryls with central and axial chirality". . p. 166 - 169,4. Retrieved 2012.