2-Iodobiphenyl

Base Information

• Chemical Name: 2-Iodobiphenyl
• CAS No.: 2113-51-1
• Molecular Formula: C12H9I
• Molecular Weight: 280.108
• Hs Code.: 29039990
• European Community (EC) Number: 218-303-3
• NSC Number: 9283
• DSSTox Substance ID: DTXSID0062185
• Nikkaji Number: J149.827D
• Wikidata: Q72483466
• Mol file: 2113-51-1.mol

Synonyms:2-Iodobiphenyl;2113-51-1;2-Iodo-1,1'-biphenyl;1,1'-Biphenyl, 2-iodo-;1-iodo-2-phenylbenzene;o-Iodobiphenyl;o-Phenyliodobenzene;2-iodo-biphenyl;Biphenyl, 2-iodo-;2-iodo-1-phenylbenzene;1,1'-Biphenyl, iodo-;MFCD00039396;64420-96-8;1,1'-biphenyl-2,3,4,5,6-d5, 2'-iodo-;NSC 9283;EINECS 218-303-3;AI3-15371;1-iodo-2-phenyl-benzene;2- Iodobiphenyl;NSC9283;2-Iodobiphenyl, 96%;1, 2-iodo-;2-Iodo-1,1'-biphenyl #;SCHEMBL154146;DTXSID0062185;QFUYDAGNUJWBSM-UHFFFAOYSA-;AMY28267;NSC-9283;CX1313;AKOS015899885;AB01776;CS-W007659;GS-6880;Biphenyl, 2-iodo- (6CI,7CI,8CI);LS-44422;SY029962;FT-0612674;FT-0698692;I0967;10.14272/QFUYDAGNUJWBSM-UHFFFAOYSA-N;EN300-6766984;doi:10.14272/QFUYDAGNUJWBSM-UHFFFAOYSA-N.1;W-107573

Chemical Property of 2-Iodobiphenyl

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 0.000295mmHg at 25°C
• Melting Point: 55-57 °C
• Refractive Index: n20/D 1.662(lit.)
• Boiling Point: 331.7 °C at 760 mmHg
• Flash Point: 150.1 °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.: Insoluble in water.
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 279.97490
• Heavy Atom Count: 13
• Complexity: 149

Purity/Quality:

99% ^*data from raw suppliers

2-Iodobiphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, T
• Hazard Codes: Xi,T
• Statements: 36/37/38-63-42/43
• Safety Statements: 26-36-36/37/39-23

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC=CC=C2I
• General Description: 2-Iodobiphenyl serves as a key precursor in the palladium-catalyzed synthesis of 9,9-disubstituted fluorenes, which are valuable for their optoelectronic and semiconductor applications. Its reaction with α-diazoesters, facilitated by optimized conditions involving P(o-tol)?, Bu?NBr, and specific bases, enables efficient C(sp2)–H activation and carbenoid insertion to construct fluorene derivatives. The versatility of 2-iodobiphenyl is highlighted by its compatibility with diverse functional groups, making it a practical building block for tailored fluorene-based materials.

Technology Process of 2-Iodobiphenyl

There total 63 articles about 2-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: 60.0%

iodobenzene (591-50-4) + C6H4I2Zn2 → 1,2-Diiodobenzene (615-42-9) + o-terphenyl (84-15-1) + 2-iodobiphenyl (2113-51-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 40 ℃; for 3h;

DOI:10.1016/S0040-4039(00)00679-1

Reference yield: 60.0%

2-iodochlorobenzene (615-41-8) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → biphenyl (92-52-4,1594-86-1) + 2-chloro-1,1'-biphenyl (2051-60-7,108321-69-3) + o-terphenyl (84-15-1) + 2-iodobiphenyl (2113-51-1)

Guidance literature:

With 6,13,14,21-tetraphenyl-22H-tribenzo[b,g,m]-[14]triphyrin(2.1.1); potassium hydroxide; tert-butyl alcohol; at 180 ℃; for 24h; Darkness;

DOI:10.1016/j.tetlet.2014.09.043

Reference yield: 60.0%

1-Bromo-2-iodobenzene (583-55-1) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → biphenyl (92-52-4,1594-86-1) + 2-Bromobiphenyl (2052-07-5) + o-terphenyl (84-15-1) + 2-iodobiphenyl (2113-51-1)

Guidance literature:

With 6,13,14,21-tetraphenyl-22H-tribenzo[b,g,m]-[14]triphyrin(2.1.1); potassium hydroxide; tert-butyl alcohol; at 180 ℃; for 24h; Darkness;

DOI:10.1016/j.tetlet.2014.09.043

upstream raw materials:

pyridine

iodobenzene

dibenzoyl peroxide

nitrobenzene

Downstream raw materials:

4-biphenyl-2-yl-benzophenone

o,p-quaterphenyl

2-phenoxy-1,1'-biphenyl

5-biphenyl-2-yl-5H-benzo[b]arsindole

Refernces

Synthesis of 9,9-Disubstituted Fluorenes from 2-Iodobiphenyls and α-Diazoesters under Palladium Catalysis

10.1021/acs.joc.7b02885

The research presents a novel method for synthesizing 9,9-disubstituted fluorenes. These fluorenes are crucial in materials science due to their unique optical and electronic properties, making them essential for applications in optoelectronics, semiconductors, and solar cells. The study introduces a straightforward approach using 2-iodobiphenyls and α-diazoesters under palladium catalysis, which involves a tandem C(sp2)–H activation/carbenoid insertion sequence. The researchers optimized the reaction conditions, finding that the combination of P(o-tol)3 as a ligand, Bu4NBr, and K2CO3/KOAc as bases in DMF solvent provided the best results. They explored the scope of various functional groups on both the 2-iodobiphenyls and α-diazoesters, demonstrating the method's versatility and compatibility with a range of substituents. The study also includes mechanistic investigations that support the involvement of palladacycles as key intermediates. The synthesized fluorenes can be further transformed, such as reducing the ester groups to hydroxyl groups, expanding their potential applications. This work provides a significant advancement in the synthesis of 9,9-disubstituted fluorenes, offering a more efficient and direct route compared to previous methods.