4,4'-Difluorobiphenyl

Base Information

• Chemical Name: 4,4'-Difluorobiphenyl
• CAS No.: 398-23-2
• Molecular Formula: C12H8F2
• Molecular Weight: 190.192
• Hs Code.: 29039990
• European Community (EC) Number: 206-910-6
• NSC Number: 4173
• UNII: O0694GMK81
• DSSTox Substance ID: DTXSID20192870
• Nikkaji Number: J43.472H
• Wikidata: Q27285154
• Mol file: 398-23-2.mol

Synonyms:Biphenyl,4,4'-difluoro- (6CI,7CI,8CI);4,4'-Difluoro-1,1'-biphenyl;4,4'-Difluorodiphenyl;NSC 4173;p,p'-Difluorobiphenyl;

Chemical Property of 4,4'-Difluorobiphenyl

Chemical Property:

• Appearance/Colour: light yellow crystal powder
• Melting Point: 88-91 °C(lit.)
• Refractive Index: 1.5678 (estimate)
• Boiling Point: 254.7 °C at 760 mmHg
• Flash Point: 88.8 °C
• PSA: 0.00000
• Density: 1.165 g/cm³
• LogP: 3.63180
• Water Solubility.: Insoluble
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 190.05940658
• Heavy Atom Count: 14
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Polyaromatics
• Canonical SMILES: C1=CC(=CC=C1C2=CC=C(C=C2)F)F

Technology Process of 4,4'-Difluorobiphenyl

There total 271 articles about 4,4'-Difluorobiphenyl 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: 83.0%

phenylmagnesium bromide (100-58-3) + 4-flourophenylmagnesium bromide (352-13-6) → biphenyl (92-52-4,1594-86-1) + 4-fluoro-biphenyl (324-74-3) + 4,4'-difluorobiphenyl (398-23-2)

Guidance literature:

phenylmagnesium bromide; 4-flourophenylmagnesium bromide; With lithium chloride; manganese(ll) chloride; In tetrahydrofuran; at -10 ℃; Inert atmosphere;

With oxygen; In tetrahydrofuran; at 10 - 20 ℃;

DOI:10.1002/ejoc.201700007

Reference yield: 79.0%

Ethyl 4-bromobutyrate (2969-81-5) + 1-Bromo-4-fluorobenzene (460-00-4) → fluorobenzene (462-06-6) + diethyl suberate (2050-23-9) + 4,4'-difluorobiphenyl (398-23-2) + ethyl 4-(4'-fluorophenyl)butanoate (1693-05-6) + butanoic acid ethyl ester (105-54-4)

Guidance literature:

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 1,10-Phenanthroline; NiI₂*3.5H₂O; sodium iodide; zinc; at 20 - 60 ℃; for 19h; chemoselective reaction;

DOI:10.1021/ja301769r

Reference yield: 74.0%

4-fluoroboronic acid (1765-93-1) → fluorobenzene (462-06-6) + 4-Fluorophenol (371-41-5) + 4,4'-difluorobiphenyl (398-23-2)

Guidance literature:

With air; sodium carbonate; palladium diacetate; In ethanol; for 24h; Yields of byproduct given; Ambient temperature;

DOI:10.1055/s-1997-710

upstream raw materials:

piperidine

Diphenyl-4,4'-bis-diazonium

4-fluoro-1-iodobenzene

diphenylene-4,4'-bisdiazonium hexafluorophosphate

Downstream raw materials:

biphenyl

4,4′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl

[1,1’-biphenyl]-4,4’-diylbis(diphenylphosphineoxide)

[(1,5-cyclooctadiene)(η6-4,4'-difluoro-1,1'-biphenyl)ruthenium(0)]

Refernces

• 1、 Salazar, Chase A.,Flesch, Kaylin N.,Haines, Brandon E.,Zhou, Philip S.,Musaev, Djamaladdin G.,Stahl, Shannon S.. "Tailored quinones support high-turnover Pd catalysts for oxidative C-H arylation with O2". . p. 1454 - 1460. Retrieved 2020.
• 2、 Lange,Askitopoulos. "-". . p. 369,379. Retrieved 1935.
• 3、 Zhu, Ming-Hui,Zhang, Xiao-Wen,Usman, Muhammad,Cong, Hengjiang,Liu, Wen-Bo. "Palladium-Catalyzed (4 + 4) Annulation of Silacyclobutanes and 2-Iodobiarenes to Eight-Membered Silacycles via C-H and C-Si Bond Activation". . p. 5703 - 5708. Retrieved 2021.
• 4、 Wong, Man Shing,Zhang, Xiao Ling. "Ligand promoted palladium-catalyzed homo-coupling of arylboronic acids". . p. 4087 - 4089. Retrieved 2001.
• 5、 Enright, Dale R.,Gogate, Akash R.,Smoliakova, Irina P.,Vasireddy, Purna C. R.. "Palladium-catalyzed aryl group transfer from triarylphosphines to arylboronic acids". . . Retrieved 2021/11/11.
• 6、 Prasanna,Bhat, Shrikanth K.,Usha,Hegde. "Ligand and Base Free Synthesis of Biaryls from Aryl Halides in Aqueous Media with Recyclable Ti0.97Pd0.03O1.97 Catalyst". . p. 3313 - 3322. Retrieved 2021/03/04.