5876-52-8

Basic information

• Product Name: 5,6-DIIODOBENZO(1,3)DIOXOLE
• Synonyms: 1,2-DIIODO-4,5-METHYLENEDIOXYBENZENE;5,6-DIIODOBENZO(1,3)DIOXOLE;5,6-diiodo-1,3-Benzodioxole
• CAS NO: 5876-52-8
• Molecular Formula: C₇H₄I₂O₂
• Molecular Weight: 373.91
• Mol File: 5876-52-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 321.5 °C at 760 mmHg
• Flash Point: 148.3 °C
• Appearance: /
• Density: 2.583 g/cm³
• Vapor Pressure: 0.000556mmHg at 25°C
• Refractive Index: 1.737
• CAS DataBase Reference: 5,6-DIIODOBENZO(1,3)DIOXOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIIODOBENZO(1,3)DIOXOLE(5876-52-8)
• EPA Substance Registry System: 5,6-DIIODOBENZO(1,3)DIOXOLE(5876-52-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 5876-52-8(Hazardous Substances Data)

Usage

General Description

"5,6-Diiodobenzo(1,3)dioxole" is a chemical compound with a range of potential applications in biochemistry and molecular biology. It features a molecular structure that includes two halogen substituents—specifically iodine—and an aromatic backbone, reminiscent of a benzene ring but with two oxygen atoms forming a dioxole ring. Owing to this unique structure, it exhibits specific reactivity and binding characteristics. However, detailed information about properties such as toxicity, reactivity, physical properties like melting and boiling point, or potential applications remains limited or unavailable. As this is a specialized compound, its primary use is likely in precise synthetic and experimental applications.

InChI:InChI=1/C7H4I2O2/c8-4-1-6-7(2-5(4)9)11-3-10-6/h1-2H,3H2

Upstream product

• 274-09-9 Methylenedioxybenzene 
• 5876-51-7 5-iodo-1,3-benzodioxole 
• 94-53-1 Piperonylic acid 
• 717903-52-1 6-(trimethylsilyl)benzo[d][1,3]dioxol-5-yl triflate 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 1012059-57-2 2-((6-iodobenzo[d][1,3]dioxol-5-yl)thio)-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-4-amine 
• 1047668-37-0 2,3-dihydro-4,9-diphenyl-1H-cyclopentanaphtho[2,3-d][1,3]dioxole 

Relevant articles and documents

Synthesis of crescent shaped heterocycle-fused aromatics via Garratt-Braverman cyclization and their DNA-binding studies

Three crescent shaped heterocycle-fused phenanthrene based systems 1–3 have been synthesized starting from benzene (or substituted benzene) 1,2-bis-propargyl alcohols. Bis-alkylation with propargylic bromides provided the key intermediate, the bis-propargyl bis-ethers. In spite of the possibility of many competing reactions, the latter underwent facile double Garratt-Braverman cyclization to provide compounds 1–3 in near quantitative yield, in a striking reaction involving the formation of four C–C bonds in a single step. Compounds 1–3 showed binding interaction with DNA, predominantly, via groove binding along with partial intercalation (combilexins). Molecular docking study supported the proposed binding modes.

Fused Amino Pyridines for the Treatment of Lung Cancer

The present invention relates to the use of compounds with fused amino pyridine core for the treatment of malignancies associated with brain and lung. The oral administration of compounds of the instant application results in effective brain penetration and provides for non-intrusive treatment of brain and lung tumors.

Rigid P-chiral phosphine ligands with tert -butylmethylphosphino groups for rhodium-catalyzed asymmetric hydrogenation of functionalized alkenes

Both enantiomers of 2,3-bis(tert-butylmethylphosphino)quinoxaline (QuinoxP*), 1,2-bis(tert-butylmethylphosphino)benzene (BenzP*), and 1,2-bis(tert-butylmethylphosphino)-4,5-(methylenedioxy)benzene (DioxyBenzP*) were prepared in short steps from enantiopure (S)- and (R)-tert-butylmethylphosphine-boranes as the key intermediates. All of these ligands were crystalline solids and were not readily oxidized on exposure to air. Their rhodium complexes exhibited excellent enantioselectivities and high catalytic activities in the asymmetric hydrogenation of functionalized alkenes, such as dehydroamino acid derivatives and enamides. The practical utility of these catalysts was demonstrated by the efficient preparation of several chiral pharmaceutical ingredients having an amino acid or a secondary amine component. A rhodium complex of the structurally simple ligand BenzP* was used for the mechanistic study of asymmetric hydrogenation. Low-temperature NMR studies together with DFT calculations using methyl α-acetamidocinnamate as the standard model substrate revealed new aspects of the reaction pathways and the enantioselection mechanism.