531508-54-0

Basic information

• Product Name: 2,2-Difluoro-4-iodobenzo[d][1,3]dioxole
• Synonyms: 2,2-Difluoro-4-iodobenzo[d][1,3]dioxole;2,2-difluoro-4-iodo-2H-1,3-benzodioxole;2,2-Difluoro-4-iodo-1,3-benzodioxole;4-Iodo-2,2-difluoro-1,3-benzodioxole
• CAS NO: 531508-54-0
• Molecular Formula: C₇H₃F₂IO₂
• Molecular Weight: 284
• Mol File: 531508-54-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 2,2-Difluoro-4-iodobenzo[d][1,3]dioxole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Difluoro-4-iodobenzo[d][1,3]dioxole(531508-54-0)
• EPA Substance Registry System: 2,2-Difluoro-4-iodobenzo[d][1,3]dioxole(531508-54-0)

Safety Data

• Hazardous Substances Data: 531508-54-0(Hazardous Substances Data)

Usage

General Description

2,2-Difluoro-4-iodobenzo[d][1,3]dioxole is a chemical compound with the molecular formula C8H4F2I. It is a dioxole derivative with fluorine and iodine substituents. 2,2-Difluoro-4-iodobenzo[d][1,3]dioxole is of interest in organic synthesis and medicinal chemistry due to its unique structure and potential biological activity. It is commonly used as a building block or intermediate in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. The fluoro and iodo substituents make this compound particularly valuable for introducing fluorine and iodine atoms into organic molecules, which can lead to enhanced biological activity and improved pharmacokinetic properties in drug development.

Upstream product

• 1583-59-1 2,2-difluoro-1,3-benzodioxole 

Downstream Products

• 531508-58-4 3-(2,2-difluoro-1,3-benzodioxol-4-yl)propyl benzenesulfonate 

Relevant articles and documents

A homologous series of O- and N-functionalized 2,2-difluoro-1,3-benzodioxoles: An exercise in organometallic methodology

The conversion of 2,2-difluoro-1,3-benzodioxole, an exceptionally acidic arene, via a 4-lithiated intermediate into more than three dozen new derivatives was conceived as a case study. The lithiated species was trapped by C0-electrophiles (4-toluenesulfonyl azide, fluorodimethoxyborane, iodine), C1-electrophiles (carbon dioxide, N,N-dimethylformamide, formaldehyde, dimethyl sulfate), C2-electrophiles (oxalic acid diesters, oxirane), C3-electrophiles (oxetane), and higher alkyl iodides. The resulting carboxylic acid 1a may be treated with organolithium compounds to afford ketones (e.g. 10) and the aldehyde 9 can be condensed with nitromethane or acetic anhydride under basic conditions. If not oxidized with chromium trioxide to the corresponding carboxylic acids, the alcohols 2b, 2c, and 2d can be transformed into the corresponding bromides (12) or sulfonates (13). Their condensation with nitrogen-containing C0-nucleophiles (hydroxylamine, sodium azide, potassium phthalimide), C1-nucleophiles (potassium cyanide), and C2-nucleophiles (aceto-nitrile) opens a convenient access to the amines 3. Other reactions gave, despite a proven track record in other areas, only moderate yields. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.