1,2-Diiodobenzene

Base Information

• Chemical Name: 1,2-Diiodobenzene
• CAS No.: 615-42-9
• Molecular Formula: C6H4I2
• Molecular Weight: 329.907
• Hs Code.: 29039990
• European Community (EC) Number: 210-425-5
• NSC Number: 29029
• DSSTox Substance ID: DTXSID0060648
• Nikkaji Number: J43.470A
• Wikidata: Q72467128
• Mol file: 615-42-9.mol

Synonyms:1,2-DIIODOBENZENE;615-42-9;o-Diiodobenzene;Benzene, 1,2-diiodo-;Benzene, o-diiodo-;diiodobenzene;MFCD00001038;EINECS 210-425-5;NSC 29029;Benzene, diiodo-;NSC29029;Benzene,2-diiodo-;1,2-diiodo-benzene;Benzene, 1,2-diiodo;Benceno, 1,2-diiodo-;1,2-Diiodobenzene, 98%;SCHEMBL28219;DTXSID0060648;BCP05858;NSC-29029;AKOS009156949;AC-9712;CS-W007538;AS-18656;SY029579;1,2-Diiodobenzene(stabilizedwithCopperchip);AM20040863;D0606;FT-0606413;EN300-39021;A20584;W-105137;1,2-diiodo-benzen;benzene,1,2-diiodo-

Chemical Property of 1,2-Diiodobenzene

Chemical Property:

• Appearance/Colour: clear yellow to brownish liquid
• Vapor Pressure: 0.00501mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: n20/D 1.718(lit.)
• Boiling Point: 284.78 °C at 760 mmHg
• Flash Point: 134.48 °C
• PSA: 0.00000
• Density: 2.47 g/cm³
• LogP: 2.89580
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Light Sensitive
• Water Solubility.: Slightly miscible with water.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 329.84025
• Heavy Atom Count: 8
• Complexity: 62.9

Purity/Quality:

98% ^*data from raw suppliers

1,2-Diiodobenzene (stabilized with Copper chip) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: C1=CC=C(C(=C1)I)I
• Uses: suzuki reaction 1,2-Diiodobenzene is useful for Suzuki reaction. It is also used in the synthesis of purino[8,9-f] phenanthridines. Further, it acts as a precursor for the synthesis of active pharmaceutical ingredients intermediate.

Technology Process of 1,2-Diiodobenzene

There total 38 articles about 1,2-Diiodobenzene 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: 90.0%

2-iodophenylamine (615-43-0) → 1,2-Diiodobenzene (615-42-9)

Guidance literature:

2-iodophenylamine; With cation-exchange resin KU-2-8; sodium nitrite; In water; at 20 ℃; for 0.75h;

With potassium iodide; In water; at 20 ℃; for 1.58333h; Further stages.;

DOI:10.1055/s-2007-990950

Reference yield: 85.0%

iodobenzene (591-50-4) → 1,2-Diiodobenzene (615-42-9) + para-diiodobenzene (624-38-4,1032416-46-8)

Guidance literature:

With dipotassium peroxodisulfate; iodine; In dichloromethane; trifluoroacetic acid; at 36 - 38 ℃; for 60h;

DOI:10.1055/s-2008-1032165

Reference yield: 81.0%

2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → 1,2-Diiodobenzene (615-42-9)

Guidance literature:

With iodine; cesium fluoride; In acetonitrile; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ol300439r

upstream raw materials:

2-iodophenylamine

1,2-diamino-benzene

benzenedizolium-2-carboxylate

1,2-bis(trimethylsilyl)benzene

Downstream raw materials:

N-phenyl piperidine

iodobenzene

benzene

1,2-bis(1-hydroxy-4-pentyn-5-yl)benzene

Refernces

• 1、 Yamada, Kodai,Yanagi, Tomoyuki,Yorimitsu, Hideki. "Generation of Organozinc Reagents from Arylsulfonium Salts Using a Nickel Catalyst and Zinc Dust". . p. 9712 - 9718. Retrieved 2021/01/09.
• 2、 Rodriguez-Lojo, Diego,Cobas, Agustin,Pena, Diego,Perez, Dolores,Guitian, Enrique. "Aryne Insertion into I-I σ-Bonds". supporting information; experimental part. p. 1363 - 1365. Retrieved 2012/05/20.