4-Iodobiphenyl

Base Information

• Chemical Name: 4-Iodobiphenyl
• CAS No.: 1591-31-7
• Deprecated CAS: 2222571-92-6
• Molecular Formula: C12H9I
• Molecular Weight: 280.108
• Hs Code.: 29039990
• European Community (EC) Number: 216-469-1
• NSC Number: 3791
• UNII: 6AN2BA2TAV
• DSSTox Substance ID: DTXSID7061807
• Nikkaji Number: J96.175B
• Wikidata: Q72483469
• Mol file: 1591-31-7.mol

Synonyms:4-iodobiphenyl;4-iodobiphenyl, 125I-labeled

Chemical Property of 4-Iodobiphenyl

Chemical Property:

• Appearance/Colour: Off-white crystalline powder
• Vapor Pressure: 0.000517mmHg at 25°C
• Melting Point: 110-114 °C
• Refractive Index: 1.64
• Boiling Point: 322.7 °C at 760 mmHg
• Flash Point: 145.8 °C
• PSA: 0.00000
• Density: 1.584 g/cm³
• LogP: 3.95820
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Water Solubility.: Slightly soluble in water.
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 279.97490
• Heavy Atom Count: 13
• Complexity: 141

Purity/Quality:

98% ^*data from raw suppliers

4-Iodobiphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N,Xn
• Hazard Codes: Xn,N,Xi
• Statements: 22-41-50/53-36/37/38
• Safety Statements: 26-39-60-61-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)I
• Uses: 4-Iodobiphenyl is used as a starting material for the preparation of p-terphenyl derivatives. It is also used in Suzuki reaction.

Technology Process of 4-Iodobiphenyl

There total 106 articles about 4-Iodobiphenyl 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: 85.0%

triphenylindium (3958-47-2) + 4-Iodobenzenediazonium o-benzenedisulfonimide → biphenyl (92-52-4,1594-86-1) + (E)-1-(4-iodophenyl)-2-phenyldiazene (21650-47-5) + 4-iodo-biphenyl (1591-31-7)

Guidance literature:

bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃; for 0.0833333h;

DOI:10.1002/ejoc.200600527

Reference yield: 75.0%

para-diiodobenzene (624-38-4,1032416-46-8) + phenylboronic acid (98-80-6) → [1,1';4',1'']terphenyl (92-94-4,94363-13-0) + 4-iodo-biphenyl (1591-31-7)

Guidance literature:

With potassium carbonate; copper-palladium; In N,N-dimethyl-formamide; at 110 ℃; for 24h;

DOI:10.1002/adsc.200303045

Reference yield: 74.0%

para-diiodobenzene (624-38-4,1032416-46-8) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → [1,1';4',1'']terphenyl (92-94-4,94363-13-0) + 4-iodo-biphenyl (1591-31-7)

Guidance literature:

With potassium tert-butylate; N,N`-dimethylethylenediamine; at 80 ℃; sealed tube; Inert atmosphere;

DOI:10.1021/ja103050x

upstream raw materials:

pyridine

iodobenzene

dibenzoyl peroxide

biphenyl

Downstream raw materials:

10-biphenyl-4-yl-phenoxazine

biphenyl

p-quaterphenyl

4,4''-diphenyl-o-terphenyl

Refernces

• 1、 Jahanshahi, Roya,Khazaee, Asma,Sobhani, Sara,Sansano, José Miguel. "G-C3N4/γ-Fe2O3/TiO2/Pd: A new magnetically separable photocatalyst for visible-light-driven fluoride-free Hiyama and Suzuki-Miyaura cross-coupling reactions at room temperature". . p. 11513 - 11526. Retrieved 2020.
• 2、 Foster et al.. "". . p. 4793. Retrieved 1972.
• 3、 Krasnokutskaya,Trusova,Filimonov. "Solid-phase iodination of arenes with the system iodine-diacetoxy(phenyl)- λ3-iodane". . p. 1750 - 1751. Retrieved 2005.
• 4、 Chaikovskii,Filimonov. "Iodination and chlorination of aromatic polycyclic hydrocarbons with iodine monochloride in aqueous sulfuric acid". . p. 1130 - 1133. Retrieved 2001.
• 5、 Darses, Sylvain,Genet, Jean-Pierre,Brayer, Jean-Louis,Demoute, Jean-Pierre. "Cross-coupling reactions of arenediazonium tetrafluoroborates with potassium aryl- or alkenyltrifluoroborates catalyzed by palladium". . p. 4393 - 4396. Retrieved 1997.
• 6、 Chahkamali, Farhad Omarzehi,Sansano, José Miguel,Sobhani, Sara. "Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media". . . Retrieved 2021/11/10.
• 7、 Bao, Yan-Sai,Cui, Xin-Yu,Han, Zheng-Bo,Li, Xin,Tang, Hong,Yang, Ming,Zhang, Yu-Yang,Zhao, Kun,Zhou, Mei-Li. "Synthesis of biaryl compounds via Suzuki homocoupling reactions catalyzed by metal organic frameworks encapsulated with palladium nanoparticles". . . Retrieved 2020/12/17.