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

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

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

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

Downstream Products

• 887144-97-0 Togni's reagent 
• 2142-70-3 2-iodoacetophenone 
• 69352-05-2 2-(2-iodophenyl)propan-2-ol 
• 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.

One-pot synthesis of hypervalent iodine reagents for electrophilic trifluoromethylation

Simplified syntheses suited for large scale preparations of the two hypervalent iodine reagents 1 and 2 for electrophilic trifluoromethylation are reported. In both cases, the stoichiometric oxidants sodium metaperiodate and tert-butyl hypochlorite have been replaced by trichloroisocyanuric acid. Reagent 1 is accessible in a one-pot procedure from 2-iodobenzoic acid in 72% yield. Reagent 2 was prepared via fluoroiodane 11 in a considerably shorter reaction time and with no need of an accurate temperature control.

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.

Substituent-controlled, mild oxidative fluorination of iodoarenes: Synthesis and structural study of aryl I(iii)- and I(v)-fluorides

We report a mild approach to the synthesis of difluoro(aryl)-λ3-iodanes (aryl-IF2 compounds) and tetrafluoro(aryl)-λ5-iodanes (aryl-IF4 compounds) using trichloroisocyanuric acid (TCICA) and potassium fluoride (

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.

Hypervalent Iodine Reagents: Thiol Derivatization with a Tetrafluoroethoxy Coumarin Residue for UV Absorbance Recognition

A new hypervalent iodine reagent (5) based on 1,2-dihydro-3,3-dimethyl-1,2-benziodoxole containing a 4-methyl-7-tetrafluoroethoxycoumarin unit as a specific UV absorber was prepared and fully characterized, including X-ray crystal structural analysis. The high reactivity of this compound towards thiols has been exploited for the selective tagging of several targets with the UV chromophore coumarin, including e.g. glutathione.

Expanding the Scope of Hypervalent Iodine Reagents for Perfluoroalkylation: From Trifluoromethyl to Functionalized Perfluoroethyl

A series of new hypervalent iodine reagents based on the 1,3-dihydro-3,3-dimethyl-1,2-benziodoxole and 1,2-benziodoxol-3-(1H)-one scaffolds, which contain a functionalized tetrafluoroethyl group, have been prepared, characterized, and used in synthetic applications. Their corresponding electrophilic fluoroalkylation reactions with various sulfur, oxygen, phosphorus, and carbon-centered nucleophiles afford products that feature a tetrafluoroethylene unit, which connects two functional moieties. A related λ3-iodane that contains a fluorophore was shown to react with a cysteine derivative under mild conditions to give a thiol-tagged product that is stable in the presence of excess thiol. Therefore, these new reagents show a significant potential for applications in chemical biology as tools for fast, irreversible, and selective thiol bioconjugation.

Preparation of iodonium ylides: Probing the fluorination of 1,3-dicarbonyl compounds with a fluoroiodane

The isolation of iodonium ylide 8, from the reaction of fluoroiodane 1 with ethyl 3-oxo-3-phenylpropanoate 5 in the presence of potassium fluoride, provides strong evidence that 1,3-dicarbonyl compounds undergo an addition reaction with fluoroiodane 1 to form an iodonium intermediate which can be deprotonated to generate an iodonium ylide. In the presence of TREAT-HF, however, the iodonium intermediate reacts to form the 2-fluoro-1,3-dicarbonyl product and we propose that fluoroiodane 1 simulates electrophilic fluorination via an addition/substitution mechanism. Further evidence to support this mechanism was obtained by successfully reacting the isolated iodonium ylide 8 with TREAT-HF, hydrochloric acid, acetic acid and p-toluenesulfonic acid to form the 2-fluoro-, 2-chloro-, 2-acetyl- and 2-tosyl-1,3-ketoesters respectively. This journal is

Electrophilic fluorination using a hypervalent iodine reagent derived from fluoride

The air and moisture stable fluoroiodane 8, readily prepared on a 6 g scale by nucleophilic fluorination of the hydroxyiodane 7 with TREAT-HF, has been used as an electrophilic fluorinating reagent for the first time to monofluorinate 1,3-ketoesters and d