80480-15-5

Usage

Uses

Used in Polymer Synthesis:
1-(Bromoacetyl)pyrene is used as an initiator for the bulk polymerization of 2-ethyl-2-oxazoline, resulting in the formation of pyrene-labeled poly(2-ethyl-2-oxazoline) (PETOX-py). This application is valuable for creating polymers with specific properties and functionalities.
Used in Fluorescent Probes:
1-(Bromoacetyl)pyrene serves as a fluorophore in the generation of podand-type fluoroionophores with two pyrene moieties. These probes are useful for detecting and sensing various ions and molecules in chemical and biological systems.
Used in Analytical Chemistry:
As a fluorescent labeling agent, 1-(Bromoacetyl)pyrene is employed for the determination of okadaic acid toxin by high-performance liquid chromatography (HPLC) with fluorescence detection. This method allows for sensitive and selective detection of the toxin in various samples.
Used in Photochemistry:
1-(Bromoacetyl)pyrene can be utilized as a photoremovable protecting group for carboxylic acids and amino acids. This application is beneficial for controlling the release of these functional groups under specific light conditions.
Used in Polymerization Processes:
As a photoinitiator, 1-(Bromoacetyl)pyrene is used in the photopolymerization of styrene with methylmethacrylate. This role is crucial for initiating the polymerization process upon exposure to light, enabling the formation of polymers with tailored properties.
Used in Ligand Synthesis:
1-(Bromoacetyl)pyrene acts as a reactant in the synthesis of potentially tetradentate pyrene-appended ligands. These ligands can be employed in various coordination chemistry and catalysis applications.
Used in Environmental Analysis:
As a derivatizing agent of dialkyl phosphates (DAP), 1-(Bromoacetyl)pyrene is used in the high-performance thin-layer chromatography (HPTLC) method for the quantitative determination of DAP in fruit juices. This application helps in assessing the levels of these compounds in food products, ensuring safety and quality.

InChI:InChI=1/C18H11BrO/c19-10-16(20)14-8-6-13-5-4-11-2-1-3-12-7-9-15(14)18(13)17(11)12/h1-9H,10H2

Upstream product

• 3264-21-9 1-acetylpyrene 
• 22118-09-8 2-bromoacetyl chloride 
• 129-00-0 pyrene 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 3264-21-9 1-acetylpyrene 
• 69795-70-6 cyclopentapyrene-3(4H)-one 
• 1233717-10-6 C₃₇H₂₄N₄O₇ 
• 1449331-28-5 benzyl 2-oxo-2-(pyren-1-yl)ethyl carbonate 
• 1449331-29-6 2-isopropyl-5-methylcyclohexyl 2-oxo-2-(pyren-1-yl)ethyl carbonate 
• 1449331-31-0 2-oxo-2-(pyren-1-yl)ethyl phenyl carbonate 
• 1449331-33-2 2-oxo-2-(pyren-1-yl)ethyl 4-nitrophenyl carbonate 
• 1499237-92-1 4-(4-(2-oxo-2-(pyren-1-yl)ethoxy)phenylthio)phthalonitrile 
• 1499237-89-6 3-(4-(2-oxo-2-(pyren-1-yl)ethoxy)phenylthio)phthalonitrile 
• 1332638-90-0 2-(1-pyrenylacetyloxy)-2'-hydroxydiphenyl sulfone 
• 1332638-89-7 2-(1-pyrenylacetyloxy)-2'-hydroxydiphenyl sulfoxide 
• 1332638-88-6 2-(1-pyrenylacetyloxy)-2'-hydroxydiphenyl sulfide 
• 1262722-98-4 2-oxo-2-(pyren-3-yl)ethyl 2-bromobenzoate 
• 1262722-99-5 2-oxo-2-(pyren-3-yl)ethyl 4-chlorobenzoate 

Relevant academic research and scientific papers

A pyrene thiazole conjugate as a ratiometric chemosensor with high selectivity and sensitivity for tin (Sn4+) and its application in imaging live cells

A new pyrene thiazole conjugate (PTC) amine fluoroionophore was synthesized and characterized. The single crystal XRD structure of PTC has been established. The fluoroionophore PTC showed selectivity toward Sn4+ by switch on ratiometric fluorescence among the 16 metal ions studied in HEPES buffer medium with a detection limit of 6.93 μM. The interaction of Sn4+ with PTC has been further supported by absorption studies, and the stoichiometry of the complex formed (2:1) has been established on the basis of fluorescence and ESI-MS. Competitive ion titrations carried out reveal that the Sn4+ can be detected even in the presence of other metal ions of bio-importance. Moreover, the utility of the fluoroionophore PTC in showing the tin recognition in live cells has also been demonstrated using Vero 76 cells as monitored by fluorescence imaging. The tin complex of PTC was isolated, and the structure and electronic properties of [PTC-Sn] has been established by DFT and TDDFT calculations. The isolated tin complex [PTC-Sn] has been used as a molecular tool for the recognition of anions on the basis of their binding affinities toward Sn4+. [PTC-Sn] was found to be sensitive and selective toward sulphide ions among the other 12 anions studied. The selectivity has been shown on the basis of the changes observed in the emission and absorption spectral studies through the removal of Sn4+ from [PTC-Sn] by S2-.

Indolizine–Squaraines: NIR Fluorescent Materials with Molecularly Engineered Stokes Shifts

The development of deep red and near infrared emissive materials with high quantum yields is an important challenge. Several classes of squaraine dyes have demonstrated high quantum yields, but require significantly red-shifted absorptions to access the N

1-(Hydroxyacetyl)pyrene a new fluorescent phototrigger for cell imaging and caging of alcohols, phenol and adenosine

1-(Hydroxyacetyl)pyrene has been introduced as a new fluorescent phototrigger for alcohols and phenols. Alcohols and phenols were protected as their corresponding carbonate esters by coupling with fluorescent phototrigger, 1-(hydroxyacetyl)pyrene. Photophysical studies of caged carbonates showed that they all exhibited strong fluorescence properties. Irradiation of the caged carbonates by visible light (≥410 nm) in aqueous acetonitrile released the corresponding alcohols or phenols in high chemical (95-97%) and quantum (0.17-0.21) yields. The mechanism for the photorelease was proposed based on Stern-Volmer quenching experiments and solvent effect studies. Importantly, 1-(hydroxyacetyl)pyrene showed as a phototrigger for rapid photorelease of the biologically active molecule adenosine. In vitro biological studies revealed that 1-(hydroxyacetyl)pyrene has good biocompatibility, cellular uptake property and cell imaging ability. The Royal Society of Chemistry and Owner Societies 2012.

1-Acetylpyrene with dual functions as an environment-sensitive fluorophore and fluorescent photoremovable protecting group

A series of new fluorescent ester conjugates of carboxylic acids including amino acids was synthesized by coupling with an environment-sensitive fluorophore 1-acetylpyrene. Interestingly, the fluorescence properties of the ester conjugates and 1-acetylpyrene were found to be highly sensitive to its surrounding environment. The results obtained from the photolysis of the ester conjugates indicated that various factors like solvent, irradiation wavelength, and the structure of the conjugates govern the rate of the photocleavage.

Synthesis of end-cap precursor molecules for (6, 6) armchair and (9, 0) zig-zag single-walled carbon nanotubes

We report the synthesis and purification of a C60H30 precursor molecule for the end-cap of a (6, 6) armchair and of a C54H24 precursor molecule for a (9, 0) zig-zag type single-walled nanotube. An approach to controlled growth of single-walled carbon nanotubes is suggested.

Quantitative Synthesis and Formation of Cyclopentapyrene 3,4-Oxide under Simulated Atmospheric Conditions

Cyclopentapyrene 3,4-oxide (2) has been synthesized in a one-step, quantitative reaction using dimethyldioxirane. The oxide, or its thermal rearrangement products cyclopentapyren-3(4H)-one and cyclopentapyren-4(3H)-one, is formed from cyclopentapyrene (1) under simulated environmental conditions. In one case these products are formed when 1 is adsorbed on model particulates and then exposed to the reaction products of tetramethylethylene and ozone in the gas phase.

Electrophilic Substitution of 3,4-Dihydrocyclopentapyrene and the 3-Ketone

Bromination of 3,4-dihydrocyclopentapyrene (1) with bromine yielded predominantly the corresponding 8-bromide; on the other hand, a similar reaction of cyclopentapyren-3(4H)-one (2) afforded the 4-bromide.The Friedel-Crafts acetylation of 1 and 2 with acetyl chloride in the presence of aluminum chloride occurred at sites 8, 6, and 1.The isomeric distribution in the acetylation of 1 was similar to that of 2.The relative reactivity of 2 with 1-acetylpyrene in acetylation was 0.75.The partial rate factor of site 1 of 1 was less than that of the corresponding position of 1-acetylpyrene, in spite of the fact that sites 6 and 8 of 1 were more reactive than the corresponding positions of 1-acetylpyrene.Nitration of 2 using acetyl nitrate in acetic anhydride took place at positions similar to the case of the acetylation of 2; however, the nitration of 1 gave the 5-nitro derivative in addition to the 8, 6 and 1-isomers.