100865-05-2

Basic information

• Product Name: 2-Propyl-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione
• Synonyms: 2-Propyl-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione;6-Bromo-2-propyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
• CAS NO: 100865-05-2
• Molecular Formula: C₁₅H₁₂BrNO₂
• Molecular Weight: 318.16528
• Mol File: 100865-05-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Propyl-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propyl-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione(100865-05-2)
• EPA Substance Registry System: 2-Propyl-6-bromo-1H-benzo[de]isoquinoline-1,3(2H)-dione(100865-05-2)

Safety Data

• Hazardous Substances Data: 100865-05-2(Hazardous Substances Data)

Upstream product

• 107-10-8 propylamine 
• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 52559-36-1 4-bromonaphthalene-1,8-dicarboximide 
• 106-94-5 propyl bromide 

Relevant articles and documents

1,8-Naphthalimide-based colorimetric and fluorescent sensor for recognition of GMP, TMP, and UMP and its application in in vivo imaging

In this study, a series of 1,8-naphthalimide-based analogs were developed for fluorescence imaging of nucleotides in Caenorhabditis elegans. In DMSO, compound 1 proved to be an effective and selective colorimetric and fluorescent sensor for recognition of GMP, TMP, and UMP over other structurally similar nucleotides. Among all the tested nucleotides, only the addition of GMP, TMP, and UMP resulted in a fluorescence color change from blue to brown with a fluorescence enhancement of more than 600-fold, with the colorless solution turning brown. NMR spectroscopic titration, theoretical calculations, and spectral tests performed using various solvent compositions confirmed that compound 1 formed multiple hydrogen bonds with the related base groups in the nucleotide. Compound 1 demonstrated its utility as a fluorescent chemosensor for detecting GMP, TMP, and UMP in in vivo imaging of GMP, TMP, and UMP in C. elegans.

A fluorescent naphthalimide NADH mimic for continuous and reversible sensing of cellular redox state

A fluorescent, naphthalimide-based, NADH mimic has been synthesised as a reversible, biocompatible, "on-off" probe for the detection of changes in intracellular redox environment (both oxidation and reduction). Interconversion was confirmed by means of el

Naphthalimide derivative-functionalized metal-Organic framework for highly sensitive and selective determination of aldehyde by space confinement-induced sensitivity enhancement effect

Facile and sensitive determination of formaldehyde (FA) in indoor environments still remains challenging. Herein, a fluorescent probe, termed PHN@MOF, was synthesized by embedding the fluorescent molecule of N-propyl-4-hydrazinenaphthalimide (PHN) into a metal-organic framework (MOF) for sensitive and visual monitoring of FA. The hydrazine group of PHN acts as the specific reaction group with FA based on the condensation reaction. The host of MOF (UiO-66-NH2) offers the surrounding confinement space required for the reaction. Owing to the enrichment effect and molecular sieve selection of UiO-66-NH2 to FA, PHN@MOF, compared with free PHN, exhibits very high sensitivity and selectivity based on space confinement-induced sensitivity enhancement (SCISE). Moreover, the fluorescence of UiO-66-NH2 offers a reference signal for FA detection. Using this ratiometric fluorescent PHN@MOF probe, a colorimetric gel plate and test paper were developed and used to visually monitor FA in air.

A glycosylation strategy to develop a low toxic naphthalimide fluorescent probe for the detection of Fe3+ in aqueous medium

A glycosylation strategy based on click chemistry was employed to develop a naphthalimide-based Fe3+ fluorescent probe with low cytotoxicity and good water-solubility. The selectivity and sensitivity to Fe3+ of three synthesized naphthalimide-based fluorescent probes follows a Nap-PZ Nap-OH > Nap-Glc trend, because the exposed toxic group of Nap-PZ was shielded by a good biocompatible group. The detection limit toward Fe3+ ion follows a Nap-PZ (7.40 × 10-6 M) > Nap-OH (2.73 × 10-7 M) > Nap-Glc (4.27 × 10-8 M) trend. Moreover, Nap-Glc could be used to detect Fe3+ in living cells. The fluorescent "off-on" response of Nap-Glc towards Fe3+ could be recognized by the naked eye, and the "off-on" fluorescent mechanism also was demonstrated by theoretical calculations. Therefore, Nap-Glc is a novel glucosyl naphthalimide fluorescent probe for environmental or biological detection of Fe3+ with low cytotoxicity and good water-solubility.

N-hydroxypropyl substituted 4-hydroxynaphthalimide: Differentiation of solvents and discriminative determination of water in organic solvents

A naphthalimide-based fluorophore (HONIOH) was designed by introducing a hydroxy unit into the 4th position of the aromatic core and a hydroxypropyl unit into the N-imide site. Photophysical properties of HONIOH were highly dependent on solvents, which was ascribed to the excited state proton transfer (ESPT) coupled with intramolecular charge transfer (ICT) mechanism. Further studies demonstrated that HONIOH can be used to recognize N, N-dimethylformamide (DMF) qualitatively and differentiate methanol from ethanol. Three control compounds were synthesized, their photophysical properties were investigated in various solvents, and experimental results revealed that hydroxyl and hydroxypropyl units contribute to the solvents differentiation ability of HONIOH. In addition, HONIOH was successfully applied as a colorimetric, fluorescent probe for the discriminative detection of trace water in organic solvents, such as fluorescence turn-on response accompanied by fluorescent color changes from light yellow to purple in DMF, and fluorescence turn-off response and blue to yellow fluorescent color changes in acetonitrile, tetrahydrofuran, and acetone. We believe that N-substituted 4-hydroxynaphthalimide derivatives may find widespread applications in chemical and biochemical sensing and imaging.

Naphthalene dianhydride based selective detection targetable fluorescent probe for monitoring exogenous Iron in living cells

A green emissive PET operating fluorescent turn-on cell permeable novel probe R1 has been successfully developed and utilized for the detection of Fe+3 in the pure aqueous system at sub-nanomolar level. Moreover, probe R1 demonstrate highly sensitive and selective towards Fe+3 over the other divalent and trivalent metal ions and was established by using fluorescence spectroscopy. The efficiency and aid of R1 was demonstrated by the fluorescence imaging of captured Fe+3 within Pollen grains by using fluorescence microscopy. These results indicate that, this is the first fluorescent turn-on PET probe to detect sub-nanomolar Fe+3 in the pure aqueous system and in cellular level.

Micellization of 4-hydroxynaphthalimides: The solvent-induced aggregation and the detection of low-level water in THF

A series of 4-hydroxy-1,8-naphthalimides were designed and synthesized for fabrication of amphiphilic dyes and aliphat-π-chromophore-hydroxy (A-π-H) structures. Their aggregation capabilities were examined in water/THF and aggregation-induced formation of micelle structures was confirmed and the structures were characterized. Moreover, the micelles were used as sensors for detection of trace-level water in THF.

Modular synthesis of 4-aminocarbonyl substituted 1,8-naphthalimides and application in single molecule fluorescence detection

Robust methodology to install amide, carbamate, urea and sulfonamide functionality to the 1,8-naphthalimide scaffold has been developed and exemplified. New benzamidonaphthalimide 6, synthesised using this approach, was found to be sensitive to base whereupon fluorescence emission strongly increases (>10-fold) and red-shifts (>4000 cm-1). The optical properties of deprotonated 6 allow for single molecule fluorescence detection, the first example of such behaviour from this class of fluorophore.

Responsive nanogel-based dual fluorescent sensors for temperature and Hg2+ ions with enhanced detection sensitivity

We report on the fabrication of thermoresponsive poly(N- isopropylacrylamide) nanogel-based dual fluorescent sensors for temperature and Hg2+ ions, and the effects of thermo-induced nanogel collapse on the detection sensitivity of Hg2+ ions. Near-monodisperse thermoresponsive nanogels were prepared via emulsion polymerization of N-isopropylacrylamide (NIPAM) and a novel 1,8-naphthalimide-based polarity-sensitive and Hg2+-reactive fluorescent monomer (NPTUA, 3). At room temperature, PNIPAM nanogels labeled with a single type of naphthalimide-based dye (NPTUA) can act as ratiometric Hg2+ probes at the nanomolar level. Upon heating above the phase transition temperature, the fluorescence intensity of NPTUA-labeled nanogels in the absence of Hg 2+ exhibit ～3.4-fold increase due to that NPTUA moieties are now located in a more hydrophobic microenvironment. Moreover, it was observed that the detection sensitivity to Hg2+ can be further improved above the nanogel phase transition temperature. At a nanogel concentration of 0.05 g L-1 and in the same Hg2+ concentration range (0-3.0 equiv.), ～10 fold and ～57 fold increase in fluorescence emission intensity ratio changes can be achieved at 25 and 40 °C, respectively.

Dual Site-Controlled and Lysosome-Targeted Intramolecular Charge Transfer-Photoinduced Electron Transfer-Fluorescence Resonance Energy Transfer Fluorescent Probe for Monitoring pH Changes in Living Cells

Acidic pH is a critical physiological factor for controlling the activities and functions of lysosome. Herein, we report a novel dual site-controlled and lysosome-targeted intramolecular charge transfer-photoinduced electron transfer-Fluorescence resonance energy transfer (ICT-PET-FRET) fluorescent probe (CN-pH), which was essentially the combination of a turn-on pH probe (CN-1) and a turn-off pH probe (CN-2) by a nonconjugated linker. Coumarin and naphthalimide fluorophores were selected as donor and acceptor to construct the FRET platform. Hydroxyl group and morpholine were simultaneously employed as the two pH sensing sites and controlled the fluorescence of coumarin and naphthalimide units by ICT and PET, respectively. The sensing mechanism of CN-pH to pH was essentially an integration of ICT, PET, and FRET processes. Meanwhile, the morpholine also can serve as a lysosome-targeted group. By combining the two data analysis approaches of the ratios of the two emission intensities (R) and the reverse ratio R′ (R′ = 1/R), the fluorescent ratio of CN-pH can show proportional relationship to pH values in a very broad range from pH 4.0 to 8.0 with high sensitivity. The probe has been successfully applied for the fluorescence imaging of the lysosomal pH values, as well as ratiometrically visualizing chloroquine-stimulated changes of intracellular pH in living cells. These features demonstrate that the probe can afford practical application in biological systems. (Figure Presented).