1,2-bis(4-iodophenyl)-ortho-carborane

Base Information

• Chemical Name: 1,2-bis(4-iodophenyl)-ortho-carborane
• CAS No.: 71482-44-5
• Molecular Formula: C₁₄H₁₈B₁₀I₂
• Molecular Weight: 548.216
• Mol file: 71482-44-5.mol

Synonyms:

Chemical Property of 1,2-bis(4-iodophenyl)-ortho-carborane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-bis(4-iodophenyl)-ortho-carborane

There total 3 articles about 1,2-bis(4-iodophenyl)-ortho-carborane 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: 58.0%

decaborane bis(dimethylsulfide) complex + 1,2-bis(4-iodophenyl)acetylene (67973-34-6) → 1,2-bis(4-iodophenyl)-ortho-carborane (71482-44-5)

Guidance literature:

In toluene; byproducts: Me2S; (N2); alkyne suspended in toluene, B compd. added, heated slowly to bathtemp. 80-85°C, N2 streamed after 2 and 4.5 h through the flask w hile the upper parts were warmed, a further quantity of B compd. added after 22 h, heated for 26 h; solvent-removed (vac.), treated with MeOH, heated cautiously, the solid sept. after 17 h, washed (MeOH), dissolved in warm C6H6, decanted, dild.with warm EtOH, cooled;

DOI:10.1016/S0022-328X(03)00313-9

Reference yield:

p-aminoiodobenzene (540-37-4) → 1,2-bis(4-iodophenyl)-ortho-carborane (71482-44-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogenchloride / acetonitrile; water / 0 °C

1.2: 0.5 h / Cooling with ice

1.3: 1 h / Cooling with ice

2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 10 h / -80 - 80 °C / Inert atmosphere

3.1: methyl iodide / 10 h / 120 °C / Sealed tube

4.1: toluene / 48 h / 100 °C / Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; methyl iodide; In tetrahydrofuran; water; toluene; acetonitrile;

Reference yield:

3,3-diethyl-1-(4-iodophenyl)triaz-1-ene (630104-26-6) → 1,2-bis(4-iodophenyl)-ortho-carborane (71482-44-5)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / tetrahydrofuran / 10 h / -80 - 80 °C / Inert atmosphere

2: methyl iodide / 10 h / 120 °C / Sealed tube

3: toluene / 48 h / 100 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; methyl iodide; In tetrahydrofuran; toluene;

upstream raw materials:

1,2-bis(4-iodophenyl)acetylene

p-aminoiodobenzene

3,3-diethyl-1-(4-iodophenyl)triaz-1-ene

Downstream raw materials:

((NC₅H₄)2NC₅H₂C₆H₄CCC₆H₄)2C₂B₁₀H₁₀

H(C₂B₁₀H₁₀C₆H₄)2I

C₂B₁₀H₁₀(C₆H₄C₂B₁₀H₁₁)2

H(C₂B₁₀H₁₀C₆H₄)2I

Refernces

• 1、 Fox, Mark A.,Howard, Judith A.K.,Hugh MacBride,Mackinnon, Angus,Wade, Kenneth. "Big macrocyclic assemblies of carboranes (big MACs): Synthesis and crystal structure of a macrocyclic assembly of four carboranes containing alternate ortho- and meta-carborane icosahedra linked by para-phenylene units". . p. 155 - 164. Retrieved 2007/10/03.