1391728-13-4

Basic information

• Product Name: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole
• Synonyms: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole;1-Fluoro-3,3-dimethyl-1,3-dihydro-1λ3,2-benziodoxole
• CAS NO: 1391728-13-4
• Molecular Formula: C₉H₁₀FIO
• Molecular Weight: 280.0779732
• EINECS: -0
• Mol File: 1391728-13-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 85.0 to 89.0 °C
• Appearance: /
• Solubility: soluble in Methanol
• CAS DataBase Reference: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole(1391728-13-4)
• EPA Substance Registry System: 1-Fluoro-3,3-dimethyl-1,2-benziodoxole(1391728-13-4)

Safety Data

• Hazardous Substances Data: 1391728-13-4(Hazardous Substances Data)

Usage

Description

1-Fluoro-3,3-dimethyl-1,2-benziodoxole is a crystalline, off-white solid that exhibits remarkable stability and can be handled under air for extended periods without significant hydrolytic decomposition. It is a versatile reagent in organic chemistry, particularly for fluorination and difluorination reactions.

Uses

Used in Pharmaceutical Industry:
1-Fluoro-3,3-dimethyl-1,2-benziodoxole is used as an electrophilic fluorination reagent for the synthesis of various pharmaceutical compounds. Its ability to effectively fluorinate easily enolizable diketo substrates makes it a valuable tool in the development of novel drugs with improved pharmacological properties.
Used in Chemical Research:
In the field of chemical research, 1-Fluoro-3,3-dimethyl-1,2-benziodoxole is employed as a reagent for the silver-catalyzed difluorination of styrenes. This reaction provides a convenient method for the introduction of difluoromethylene groups into organic molecules, which can be crucial for the synthesis of complex organic compounds and the study of their properties.
Used in Material Science:
1-Fluoro-3,3-dimethyl-1,2-benziodoxole can also be utilized in the development of new materials with enhanced properties. The incorporation of fluorine atoms into the molecular structure can significantly alter the physical and chemical characteristics of materials, making them more suitable for specific applications, such as in the electronics or aerospace industries.

Upstream product

• 88-67-5 2-Iodobenzoic acid 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 1459128-73-4 1-tosyloxy-3,3-dimethyl-1,3-dihydro-λ³-benzo[d][1,2]iodoxole 
• 1459128-72-3 1-trifluoroacetoxy-3,3-dimethyl-1,3-dihydro-λ³-benzo[d][1,2]iodoxole 
• 69429-70-5 1-hydroxy-3,3-dimethyl-1,3-dihydro-λ³-benzo[d][1,2]iodoxole 
• 69352-03-0 1-bromo-3,3-dimethyl-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole 
• 73602-61-6 triethylamine tris(hydrogen fluoride) 
• 134-20-3 2-carbomethoxyaniline 
• 69352-04-1 1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole 
• 69352-05-2 2-(2-iodophenyl)propan-2-ol 
• 610-97-9 o-iodo-methyl-benzoic acid 

Downstream Products

• 887144-97-0 Togni's reagent 
• 117341-66-9 5-Methyl-3-phenyl-6H-[1,2]oxazine 

Relevant articles and documents

Determining the predominant tautomeric structure of iodine-based group-transfer reagents by 17O NMR spectroscopy

Cyclic benziodoxole systems have become a premier scaffold for the design of electrophilic transfer reagents. A particularly intriguing aspect is the fundamental II–IIII tautomerism about the hypervalent bond, which has led in certain cases to a surprising re-evaluation of the classic hypervalent structure. Thus, through a combination of 17O NMR spectroscopy at natural abundance with DFT calculations, we establish a convenient method to provide solution-phase structural insights for this class of ubiquitous reagents. In particular, we confirm that Shen’s revised, electrophilic SCF3-transfer reagent also adopts an "acyclic" thioperoxide tautomeric form in solution. After calibration, the approach described herein likely provides a more general and direct method to distinguish between cyclic and acyclic structural features based on a single experimental 17O NMR spectrum and a computationally-derived isotropic shift value. Furthermore, we apply this structural elucidation technique to predict the constitution of an electrophilic iodine-based cyano-transfer reagent as an NC–I–O motif and study the acid-mediated activation of Togni's trifluoromethylation reagent.

A general method for one-step synthesis of monofluoroiodane(III) reagents using silver difluoride

Herein we report a new general method for one-step synthesis of four kinds of fluoroiodane(III) reagents by treating the corresponding aryl iodides with silver difluoride (AgF2). This is the first method applicable for the synthesis of all four fluoroiodane(III) reagents including p-iodotoluene difluoride (1), fluoro-benziodoxole (2), fluoro-benziodoxolone (3), and fluoro-N-acetylbenziodazole (4). AgF2 was firstly employed in the direct oxidative fluorination of iodobenzene and thus has shown its outstanding oxidation and fluorine-transfer ability. The use of AgF2 has improved the synthesis of fluoroiodane(III) reagents by shortening the reaction steps, avoiding the use of hazardous reagents, and simplifying the experimental operations. It was worth noting that we have developed the first one-step direct synthetic method for 3, while 3 can only be synthesized through Cl→F ligand exchange reaction previously.

Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions

An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.