80480-15-5

Basic information

• Product Name: 1-(BROMOACETYL)PYRENE
• Synonyms: 1-(BROMOACETYL)PYRENE;2-bromo-1-(1-pyrenyl)Ethanone;2-bromo-1-(pyren-3-yl)ethanone;2-broMo-1-(pyren-1-yl)ethanone;1-(Bromoacetyl)pyrene 97%
• CAS NO: 80480-15-5
• Molecular Formula: C₁₈H₁₁BrO
• Molecular Weight: 323.18
• Product Categories: C15 to C38;Carbonyl Compounds;Ketones
• Mol File: 80480-15-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 129-131 °C(lit.)
• Boiling Point: 476.7 °C at 760 mmHg
• Flash Point: 109.3 °C
• Appearance: /
• Density: 1.563 g/cm³
• Vapor Pressure: 2.98E-09mmHg at 25°C
• Refractive Index: 1.823
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(BROMOACETYL)PYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(BROMOACETYL)PYRENE(80480-15-5)
• EPA Substance Registry System: 1-(BROMOACETYL)PYRENE(80480-15-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 22-26-36/37/39-45
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 80480-15-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

Uses

1-(Bromoacetyl)pyrene is suitable for use in the following studies:As an initiator in the bulk polymerization of 2-ethyl-2-oxazoline to generate pyrene labelled poly(2-ethyl-2-oxazoline) (PETOX-py).As a fluorophore in the generation of podand-type fluoroionophores with two pyrene moieties.As a fluorescent labeling agent for the determination of okadaic acid toxin by HPLC with fluorescence detection.It may also be used in the following studies:As a photoremovable protecting group for carboxylic acids and amino acids.As a photoinitiator in the photopolymerization of styrene with methylmethacrylate.As a reactant in the synthesis of potentially tetradentate pyrene appended ligands.As a derivatizing agent of dialkyl phosphates (DAP) in the HPTLC method of quantitative determination of DAP in fruit juices.

General Description

1-(Bromoacetyl)pyrene (BAP) is a pyrene derivative. It has been synthesized by reacting cupric bromide with 1-acetylpyrene. Studies suggest that the introduction of a bromoacetyl chromophoric moiety to pyrene drastically increases the photoinitiating efficiency of pyrenes.

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

Downstream Products

• 3264-21-9 1-acetylpyrene 
• 69795-70-6 cyclopentapyrene-3(4H)-one 
• 27208-37-3 cyclopenta[c,d]pyrene 
• 73473-56-0 3,4-dihydrocyclopentapyrene-4(3H)-one 
• 69795-73-9 3-hydroxy-3,4-dihydrocyclopentapyrene 
• 1233717-10-6 C₃₇H₂₄N₄O₇ 
• 1262722-93-9 2-oxo-2-(pyren-3-yl)ethyl 2-phenylacetate 
• 1262723-03-4 tert-butyl (S)-1-((2-oxo-2-(pyren-3-yl)ethoxy)carbonyl)-2-phenylethylcarbamate 
• 1262722-96-2 2-oxo-2-(pyren-3-yl)ethyl 4-methylbenzoate 
• 1262722-97-3 2-oxo-2-(pyren-3-yl)ethyl 4-methoxybenzoate 
• 1262722-95-1 2-oxo-2-(pyren-3-yl)ethyl benzoate 
• 1262722-99-5 2-oxo-2-(pyren-3-yl)ethyl 4-chlorobenzoate 
• 1262722-98-4 2-oxo-2-(pyren-3-yl)ethyl 2-bromobenzoate 
• 1332638-88-6 2-(1-pyrenylacetyloxy)-2'-hydroxydiphenyl sulfide 

Relevant articles and documents

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-.

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.