125677-99-8

Basic information

• Product Name: 1,3-Benzenediamine, 4,6-diiodo-
• Synonyms: 4,6-diiodobenzene-1,3-diaMine;2,4-Diamino-1,5-diiodobenzene;4,6-diiodo-1,3-phenylenediamine
• CAS NO: 125677-99-8
• Molecular Formula: C₆H₆I₂N₂
• Molecular Weight: 359.927
• Mol File: 125677-99-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Benzenediamine, 4,6-diiodo-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzenediamine, 4,6-diiodo-(125677-99-8)
• EPA Substance Registry System: 1,3-Benzenediamine, 4,6-diiodo-(125677-99-8)

Safety Data

• Hazardous Substances Data: 125677-99-8(Hazardous Substances Data)

Usage

Derivative of benzene

Yes

Explanation

1,3-Benzenediamine, 4,6-diiodois derived from benzene, a basic aromatic hydrocarbon with a six-carbon ring structure.

Explanation

The compound contains two iodine atoms attached to the 4th and 6th positions of the benzene ring.

Explanation

1,3-Benzenediamine, 4,6-diiodois utilized in the synthesis of various pharmaceuticals and organic compounds. It is also used as a reagent in the production of dyes, pigments, and polymers.

Explanation

The compound has potential use in medical imaging as a contrast agent, enhancing the visibility of internal structures during radiographic and CT scans.

Explanation

1,3-Benzenediamine, 4,6-diiodois considered hazardous and should be handled with care to avoid skin and eye irritation upon contact.

Explanation

To minimize the risk of skin and eye irritation, it is essential to wear appropriate protective gear and follow safety guidelines when handling this compound.

Iodine atoms

Two

Common uses

Pharmaceutical synthesis, organic compounds, dyes, pigments, and polymers

Potential medical application

Contrast agent for radiographic and computed tomography (CT) scans

Hazardous nature

Yes

Safety precautions

Wear protective gear (gloves, goggles, etc.) and follow proper handling procedures

Upstream product

• 615-28-1 o-phenylenediamine dihydrochloride 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 7553-56-2 iodine 
• 127-09-3 sodium acetate 
• 541-69-5 m-phenylenediamine dihydrochloride 
• 108-45-2 m-phenylenediamine 
• 102-28-3 m-acetamide aniline 
• 123765-81-1 acetic acid-(3-amino-4,6-diiodo-anilide) 

Downstream Products

• 130049-16-0 eicosa-7,9,11,13-tetrayne 
• 1159200-48-2 N,N'-(4,6-diiodo-1,3-phenylene)bis(p-toluenesulfonamide) 
• 1353988-96-1 dimethyl 7-amino-6-iodoquinoline-2,4-dicarboxylate 
• 1353988-99-4 7-amino-6-iodo-4-methoxycarbonylquinoline-2-carboxamide 
• 1353988-97-2 7-amino-6-iodoquinoline-2,4-dicarboxamide 
• 1621060-84-1 C₁₆H₂₄N₂Si₂ 

Relevant articles and documents

Nonmetal-catalyzed iodination of arenes with iodide and hydrogen peroxide

Oxidative iodination of arenes was carried out with one equivalent of KI and two equivalents of 30% hydrogen peroxide in MeOH in the presence of strong acid. Reactions of various substituted anisoles, phenols and anilines, as well as mesitylene and uracil, were selective and effective with very good yields of isolated halogenated aromatic molecules.

Gold-Catalyzed Synthesis of π-Extended Carbazole-Based Systems and their Application as Organic Semiconductors

Herein we describe a gold-catalyzed bidirectional synthesis of N-heteropolycyclic compounds bearing carbazole moieties – namely π-extended benzodicarbazoles and π-extended indolocarbazoles. Overall, four previously unknown core structures were synthesized. This approach is convergent, modular and the gold-catalyzed key step comprises of a cascade reaction starting from stable di-azido compounds. The obtained molecules were fully characterized and their optical and electronic properties as well as their performance in organic thin-film transistors generated by vacuum deposition were studied. Charge-carrier mobilities of up to 0.3 cm2/Vs were measured. (Figure presented.).

Synthesis and characterization of a main-chain donor-acceptor type low-bandgap polymer by post-functionalization of a poly(arylene ethynylene)

I report a facile synthetic route for synthesizing a main-chain donor-acceptor type polymer containing strong electron donating dialkylamino groups and strong electron accepting 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) units. To accomplish this, an electron donating monomer 4,6-diethynyl-N,N,N,N- tetrahexylbenzene-1,3-diamine was successfully synthesized by converting two carbaldehyde groups in the corresponding monomer into acetylene groups using lithium trimethylsilyldiazomethane via Colvin rearrangement. This electron donating monomer was then polymerized with a carbonyl-activated diiodide monomer to afford an electron-donating π-conjugated precursor polymer with a reasonably high molecular weight, which was further reacted with TCNE via cycloaddition/retroelectrocyclization reaction under mild conditions to afford the target polymer with a low bandgap energy (Egopt=1.40eV and EgCV=1.10eV) arising from strong intramolecular charge-transfer interactions between electron donors and acceptors in the polymer.