129053-33-4

Basic information

• Product Name: Benzene, [[(1E)-2-fluoro-1-propyl-1-pentenyl]seleno]-
• CAS NO: 129053-33-4
• Molecular Formula: C14H19FSe
• Molecular Weight: 285.263
• Mol File: 129053-33-4.mol

Chemical Properties

• CAS DataBase Reference: Benzene, [[(1E)-2-fluoro-1-propyl-1-pentenyl]seleno]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [[(1E)-2-fluoro-1-propyl-1-pentenyl]seleno]-(129053-33-4)
• EPA Substance Registry System: Benzene, [[(1E)-2-fluoro-1-propyl-1-pentenyl]seleno]-(129053-33-4)

Safety Data

• Hazardous Substances Data: 129053-33-4(Hazardous Substances Data)

Upstream product

• 13709-36-9 xenon difluoride 
• 1942-45-6 4-Octyne 
• 66166-06-1 phenylselenotrimethylplumbane 
• 4848-71-9 trimethylstannyl phenyl selenide 
• 61501-51-7 (trimethyl)(phenylseleno)germane 
• 34837-55-3 Phenylselenyl bromide 
• 1666-13-3 diphenyl diselenide 
• 76773-18-7 phenylselenyl trifluoride 
• 72726-46-6 tert-butyl(dimethyl)(phenylseleno)silane 
• 33861-17-5 phenyl trimethylsilyl selenide 
• 129803-02-7 benzeneselenyl fluoride 
• 71098-88-9 N-phenylselanylphthalimide 

Downstream Products

• 129053-43-6 C₁₄H₁₉FOSe 

Relevant articles and documents

Phenylselenofluorination of alkenes and alkynes promoted by difluoroiodotoluene and diphenyldiselenide

The oxidation of diphenyldiselenide with 4-iodotoluene difluoride (DFIT) in dichloromethane produces in situ an efficient phenylselenofluorinating agent of alkenes and internal alkynes.

First detection of a selenenyl fluoride ArSe-F by NMR spectroscopy: The nature of Ar2Se2/XeF2 and ArSe-SiMe 3/XeF2 reagents

Arylselenenyl fluorides ArSeF are obtained from diselenides Ar 2Se2 or arylselenotrimethylsilanes ArSe-SiMe3, and XeF2. They are detected by low-temperature 19F and 77Se NMR spectroscopy. Substitution in the ortho position of the aromatic ring to provide electronic or steric protection is a requirement for their formation. ArSe-F compounds decompose according to 3 ArSe-F → [ArSe-SeF2Ar] + ArSe-F- → ArSeF3 + Ar 2Se2. Reaction energies for this disproportionation as well as that of the sulfur and tellurium homologues have been calculated with MP2, CCSD(T,) and B3 LYP methods. They were found to be increasingly exothermic in the sequence S 77Se and 19F chemical shifts have been calculated by GIAO-MP2 and GIAO-B3LYP methods and are in good agreement with experimental values.

PhSeOTf-Et3N·3HF and PhSeSbF6-Et3N·3HF as new PhSe-F equivalents in the fluoroselenenylation of actylenes

The novel reagents PhSeOTf-Et3N·3HF and PhSeSbF6-Et3N·3HF act as PhSe-F equivalents in the fluoroselenenylation of alkynes. Oct-4-yne, cycloundecyne and cyclododecyne, as well as the unsymmetrical alkynes Ph-C≡C-Me and Bu-C≡C-R (R = Me, Et, iPr and tBu) give the corresponding (E)-fluoro(phenylseleno)alkenes in preparative yields. The reagent PhSeOTf-Et3N·3HF gives a similar product composition of regioisomers to Ph2Se2-XeF2 in addition reactions to Bu-C≡C-R. This is indicative of a similar reaction mechanism of the reagents. Probably a selenirenium ion acts as an intermediate. X-Ray single crystal structure analysis of (E)-1-fluoro-2-phenylselenocycloundecene confirms the trans-addition of [PhSe-F] to cycloundecyne.

Reactions of RSe-EMe3 (E = Si, Ge, Sn, Pb) with XeF2 - RSe-F equivalents in the fluoroselenenylation of acetylenes

Selenides of the type R1Se-EMe3 (E = Si, Ge, Sn, Pb) react with xenon difluoride by cleavage of the Se-E bond to yield the R1Se-F intermediate and the fluorides Me3E-F, whereas the Se-C bond in PhSe-tBu (E = C) is stable against XeF2. The presence of R1Se-F intermediates is confirmed by addition to acetylenes (4-octyne, 3-hexyne). Thus, the fluoroselenenylation of acetylenes gives fluoro(organylseleno)olefins in preparative yields. In the cases of E = Si, Ge, Sn, and Pb, aryl and n-alkyl groups are suitable as the substituent R1. The X-ray crystal structural analysis of (E)-3-(p- carboxyphenylseleno)-4-fluorohex-3-ene - the first example of an uncharged fluoroselenoolefin synthesized from p-EtO2C-C6H4-Se-SnMe3, XeF2, and 3- hexyne followed by an ester hydrolysis - shows that the addition of the selenenylfluoride intermediate to the acetylene proceeds via a trans- addition, as is known for the R2Se2-XeF2 reagents.

13C, 19F and 77Se NMR study of vicinal (E)-fluoro(organylseleno)olefins and [(E)-fluoroalkenyl]diorganylselenonium salts

13C, 19F and 77Se NMR spectra of the (E)-fluoro(organylseleno)olefins R1(F)Cα=CβR2(SeR3) and the [(E)-fluoroalkenyl]diorganylselenonium salts R1(F)Cα/

Fluoroselenylation of acetylenes with xenon difluoride-diorganyl diselenides and xenon difluoride-phenylseleno(trialkyl)silanes

A new, efficient method of fluoroselenenylation of terminal, and open-chain symmetric and unsymmetric disubstituted acetylenes and cycloalkynes, gives vicinal (E)-fluoroalkenyl selenides in moderate to high yields by addition of selenenyl fluoride equivalents. These are formed in situ from xenon difluoride and diaryl, dibenzyl or primary and secondary dialkyl diselenides. Alternatively, the benzeneselenenyl fluoride equivalent is formed by treatment of more reactive phenylselenotrialkylsilanes with xenon difluoride. The regiochemistry of the addition is strongly dependent on the steric effects of substituents bonded to the acetylene.

Phenylthio (and phenylseleno)fluorination of alkenes and alkynes using N-phenylthio (and phenylseleno)phthalimide combined with pyridine*9HF or Et3N*3HF complexes

N-Phenylthiophthalimide and N-phenylselenophthalimide combined with pyridine*9HF or Et3N*3HF complexes allow the formal addition of elements of PHSF or PhSeF across the carbon-carbon double or triple bond by a one-pot reaction.Pyridine*9HF, a strongly aci

Fluoroselenenylation of Alkynes

Benzeneselenenyl fluoride equivalent was generated in situ by the reaction of silver(I) fluoride with benzeneselenenyl bromide in dichloromethane under ultrasound irradiation.Treatment of internal alkynes with this reagent afforded 2-fluoro-1-alkenyl phen

Phenylselenofluoration d'alcynes

The electrophilic anti-addition of the elements of benzeneselenenyl fluoride towards carbone-carbone triple bonds is performed by a one-pot reaction of N-phenylselenophthalimide and triethylamine tris-hydrofluoride with disubstituted alkynes ; starting from monosubstituted alkynes, the reaction proceeds further to afford vinylic diselenated compounds after hydrofluoric acid elimination. Some products of mono-addition could be transformed into vinylic or allenic fluorides.