61378-39-0

Basic information

• Product Name: Benzene, (1-fluoro-2-iodoethenyl)-, (Z)-
• CAS NO: 61378-39-0
• Molecular Formula: C8H6FI
• Molecular Weight: 248.039
• Mol File: 61378-39-0.mol

Chemical Properties

• CAS DataBase Reference: Benzene, (1-fluoro-2-iodoethenyl)-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (1-fluoro-2-iodoethenyl)-, (Z)-(61378-39-0)
• EPA Substance Registry System: Benzene, (1-fluoro-2-iodoethenyl)-, (Z)-(61378-39-0)

Safety Data

• Hazardous Substances Data: 61378-39-0(Hazardous Substances Data)

Upstream product

• 932-88-7 1-iodo-2-phenylethyne 
• 536-74-3 phenylacetylene 
• 1026856-94-9 C₁₅H₁₃F₂I 

Downstream Products

• 133512-77-3 (1-fluorobut-1-en-3-yne-1,4-diyl)dibenzene 
• 671-18-1 (Z)-(1-fluoro-2-phenylethenyl)benzene 
• 133512-86-4 ((1Z,3E)-1-fluorobuta-1,3-diene-1,4-diyl)dibenzene 

Relevant articles and documents

Preparation of vincinal hetero 1,2-dihalo-olefins by using aqueous hydrohalic acid

An efficient simple method was developed to prepare hetero E-1,2-dihaloolefins from mono- or disubstituted alkynes, in which, NXS (X = Br, I) was utilized as the electrophilic reagents and aqueous hydrohalic acid as the nucleophile. Moreover, Z-type dihalogenation olefins could be obtained from the terminal silylacetylene.

Stereodivergent Alkyne Hydrofluorination Using Protic Tetrafluoroborates as Tunable Reagents

The discovery of safe, general, and practical procedures to prepare vinyl fluorides from readily available precursors remains a synthetic challenge. The metal-free hydrofluorination of alkynes constitutes an attractive though elusive strategy for their preparation. Introduced here is an inexpensive and easily handled reagent that enables the development of simple and scalable protocols for the regioselective hydrofluorination of alkynes to access both the E and Z isomers of vinyl fluorides. These reaction conditions were suitable for a diverse collection of alkynes, including several highly functionalized pharmaceutical derivatives. Computational and experimental mechanistic studies support C?F bond formation through vinyl cation intermediates, with the E- and Z-hydrofluorination products forming under kinetic and thermodynamic control, respectively.

Selective Mono- And Dialkynylation of 1-Fluoro-2,2-diiodovinylarenes Using Pd-Catalyzed Decarboxylative Coupling Reactions

Palladium-catalyzed decarboxylative coupling reactions using alkynoic acids and 1-fluoro-2,2-diiodovinylarenes provide mono- and dialkynylfluoroalkenes with high selectivity. When the reaction was conducted using DBU/DMSO, the hydrodeiodinated monoalkynyl

Controlled Single and Double Iodofluorination of Alkynes with DIH- and HF-Based Reagents

A novel protocol for the regio- and stereoselective iodofluorination of internal and terminal alkynes using 1,3-diiodo-5,5,-dimethylhydantoin and HF-based reagents is disclosed. This approach is used to prepare a fluorinated tamoxifen derivative in two steps from commercially available starting materials. A facile method enabling controlled regioselective double iodofluorination of terminal alkynes is also presented.

Sequential Functionalization of Alkynes and Alkenes Catalyzed by Gold(I) and Palladium(II) N-Heterocyclic Carbene Complexes

The iodination of terminal alkynes for the synthesis of 1-iodoalkynes using N-iodosuccinimide in the presence of a AuI-NHC (NHC=N-heterocyclic carbene) catalyst is reported. A series of aromatic alkynes was transformed successfully into the corresponding 1-iodoalkynes in good to excellent yields under mild reaction conditions. The further use of these compounds as organic building blocks and the advantageous choice of metal-NHC complexes as catalysts for alkyne functionalization were further demonstrated by performing selective AuI-catalyzed hydrofluorination to yield (Z)-2-fluoro-1-iodoalkenes, followed by a Suzuki–Miyaura cross-coupling with aryl boronic acids catalyzed by a PdII-NHC complex to access trisubstituted (Z)-fluoroalkenes. All methodologies can be performed sequentially with only minor variations in the optimized individual reaction conditions, maintaining high efficiency and selectivity in all cases, which therefore, provides straightforward access to valuable fluorinated alkenes from commercially available terminal alkynes.

Stereoselective synthesis of iodofluoroalkenes by iodofluorination of alkynes using IF5-pyridine-HF

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Stereoselective synthesis of fluoroalkenes via (Z)-2-fluoroalkenyliodonium salts

Stereoselective synthesis of fluoroalkenes is described. (Z)-2-Fluoro-1-alkenyl(phenyl)iodonium tetrafluoroborates (1) were synthesized stereoselectively in good yields by Michael-type addition of HF to 1-alkynyl(phenyl)iodonium tetrafluoroborates (2) with a commercially available HF reagent, hydrofluoric acid or Et3N-3HF. Pd-catalyzed cross-coupling reactions using 1 gave (Z)-2-fluoro-1-alkene derivatives in moderate yields. The treatment of 1 with KI in the presence of a catalytic amount of CuI gave (Z)-2-fluoro-1-iodo-1-alkenes (3). Pd-catalyzed cross-coupling reactions of 3 gave better results than that of 1, and a variety of (Z)-2-fluoro-1-alkene derivatives were synthesized in good yields.

Iodofluorination of alkenes and alkynes promoted by iodine and 4-iodotoluene difluoride

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Regio- and Stereoselective Synthesis of Fluorinated Enynes and Dienes via 1,1- or 1,2-Halofluoroalkenes

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