92874-17-4

Basic information

• Product Name: 6-bromo-2-butyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
• Synonyms: 6-bromo-2-butyl-1H-benzo[de]isoquinoline-1,3(2H)-dione;4-Bromo-N-butylnaphthalimide
• CAS NO: 92874-17-4
• Molecular Formula: C₁₆H₁₄BrNO₂
• Molecular Weight: 332.19186
• Mol File: 92874-17-4.mol
• Article Data: 111

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-bromo-2-butyl-1H-benzo[de]isoquinoline-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-2-butyl-1H-benzo[de]isoquinoline-1,3(2H)-dione(92874-17-4)
• EPA Substance Registry System: 6-bromo-2-butyl-1H-benzo[de]isoquinoline-1,3(2H)-dione(92874-17-4)

Safety Data

• Hazardous Substances Data: 92874-17-4(Hazardous Substances Data)

Upstream product

• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 109-73-9 N-butylamine 
• 109-65-9 1-bromo-butane 
• 52559-36-1 4-bromonaphthalene-1,8-dicarboximide 
• 81-84-5 1,8-Naphthalic anhydride 
• 21563-29-1 4-bromo-1,8-naphthalene anhydride 
• 83-32-9 acenaphthene 
• 2051-98-1 5-bromoacenaphthene 

Downstream Products

• 862994-69-2 1-benzoyl-3-[2-(2-butyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-ylamino)-ethyl]-thiourea 
• 1135916-51-6 4-(9-phenyl-carbazol-3-yl)-N-butyl-1,8-naphthalimide 
• 1135916-54-9 4,4'-(9-phenyl-carbazol-3,6-diyl)-N-butyl-1,8-naphthalimide 
• 1241374-43-5 4-(5'-ethynylsalicylaldehyde)-N-butyl-1,8-naphthalimides 
• 1258880-17-9 C₂₉H₂₂N₂O₂ 
• 1228882-51-6 2-butyl-6-(3,4-dihydroxyphenylamino)benzo[de]isoquinoline-1,3-dione 
• 1228882-53-8 C₂₂H₁₈N₂O₄ 
• 1267600-37-2 5-butyl-10-(4-methoxyphenyl)-10-phenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione 
• 1314663-69-8 C₂₃H₁₉NO₅ 
• 1375415-31-8 C₃₅H₄₂N₄O₃Si 
• 852288-07-4 N-butyl-4-(phenylethynyl)-1,8-naphthalimide 
• 1425378-90-0 C₂₄H₂₂N₄O₃ 
• 1425396-95-7 4-(bis(2-(ethylthio)ethyl)amino)-N-n-butyl-1,8-naphthalimide 
• 1426076-29-0 C₂₉H₂₆N₂O₂Se 

Relevant articles and documents

Novel 1,8-naphthalimide dye for multichannel sensing of H+ and Cu2+

A novel 1,8-naphthalimide dye with simple structure has been produced by a facile synthetic method for colorimetric and fluorescent sensing of H+ and Cu2+. In CH3CN/H2O (1/1, v/v), the dye could monitor H+ using dual channels (ratiometric absorbance and fluorescence intensity change) from pH 6.2 to 12.0. Meanwhile, in the pH range of 1.9–5.2, the dye could also be used to detect Cu2+ using triple channels [ultraviolet–visible (UV–Vis) absorption, fluorescence intensity reduction, as well as fluorescence blueshift]. The detection limits for Cu2+ evaluated by colorimetric and fluorescent titration were 6.10?×?10?7 and 2.62?×?10?7?M, respectively. The dye exhibited specific selectivity and sensitivity for H+ and Cu2+ over various coexisting metal ions. Moreover, the sensing mechanism of the dye for H+ and Cu2+ was carefully examined.

Combination of sensor potential and antimicrobial activity of a new 4-(2-dimethylaminoethyloxy)-N-buthyl-1,8-naphthalimide

A blue emitting 4-(2-dimethylaminoethyloxy)-N-buthyl-1,8-naphthalimide bearing a dimethylaminoethyloxy group as a receptor fragment for metal ions and protons has been designed and synthesized. The basic photophysical properties of the compound have been investigated in organic solvents of different polarity. The detection of different metal cations (Pb2+, Cu2+, Cd2+, Co2+, Zn2+and Mn2+) has been studied by fluorescence spectroscopy. Depending on pH, the new compound shows "off-on" switching from alkaline to acid media. A new complex of Cu(II) with the 4-(2-dimethylaminoethyloxy)-N-buthyl-1,8-naphthalimide has been synthesized and characterized. The antibiotic activity of the complex was evaluated against some bacterial and yeast cultures.

A novel ratiometric fluorescent probe for quantitative detection of isocyanates in air

Isocyanates are important industrial raw materials, but they are hazardous to human health. Especially, gaseous isocyanates cause serious public health problems. Therefore, it is significant to monitor isocyanates in air. In this work, a novel ratiometric fluorescent probe based on a new fluorophore platform, which is designed by inserting a styryl π-bridge between donor and acceptor units of 1, 8-naphthalimide, was developed for quantitative detection of gaseous isocyanates. In the presence of isocyanates, fluorescence of probe solution changed from orange to yellow-green, which caused by alteration of substituent at the 4th position of styryl group resulted from reaction between isocyanates and probe, thus achieving ratiometric detection for isocyanates. And this probe exhibited a fast, sensitive and selective response towards isocyanates. Furthermore, probe solution absorption method was employed to detect quantitatively isocyanates in air. This strategy may be a powerful tool for monitoring isocyanates in air, and also provide a referable approach for detection of volatile organic compounds in air.

Green synthesis of fluorescent N,O-chelating hydrazone Schiff base for multi-analyte sensing in Cu2+, F? and CN? ions

A colorimetric and fluorometric hydrazone Schiff's base derived from dehydroacetic acid by three-steps and high-yield syntheses under green approach employing ethanol as a solvent has been prepared. Multi-analyte sensing for both metal cation (Cu2+) and anions (F? and CN?), with high sensitivity and competitive selectivity, was encountered. The sensing mechanism of anion detection found to be deprotonation of N–H and O–H moieties in the presence of ions. However, metal cation like copper(II) ions chelation with sensor, leads to diminish intra-molecular charge transfer (ICT) with chelation induced quenching of fluorescence (CHQF). Contrary, anionic interaction ensued in heightened ICT as well as photo-induced electron transfer (PET) processes. The Job's plots interpretation rendered stoichiometry of 2:1 with Cu2+/F? and 1:1 with CN?. Moreover, the detection limits of 0.962 ppm (Cu2+), 0.023 ppm (F?) and 0.073 ppm (CN?) were much lower than WHO guidelines. Further, either water or methanol was employed to differentiate F?/CN? ions with sensor in THF, with prominent visible naked eye and fluorometric responses.

A two-channel chemosensor for the optical detection of carboxylic acids, including cholic acid

A neutral receptor, in which a urea fragment has been equipped with two naphthaleneimide subunits, on interaction with acetate, in a DMSO solution, undergoes deprotonation of one of the N-H fragments; an event which is signalled by a yellow-to-red colour change and by the quenching of the blue fluorescence of the naphthalneimide subunit, with no competition by a number of anions (phosphate, nitrate, sulfate, chloride or bromide). This procedure can be employed for the visual and spectroscopic detection of cholic acid, even in presence of the other competing bile acids, such as glycocholic and taurocholic. The Royal Society of Chemistry 2005.

Turn-on fluorescent detection of strong acids based on a naphthalimide-indoline hybrid

A naphthalimide-indoline hybrid (1) was developed as a pH-sensitive turn-on fluorescent probe. Probe 1 displays a weak fluorescence intensity in pH span of 2.5–11.0 owing to a photo-induced electron transfer (PET) from the indoline moiety to the naphthalimide. However, the PET process is suppressed under the pH of 2.5, showing a strong fluorescence signal at 430?nm. The turn-on fluorescent change of 1 is selective for the acidity (H+) over other anions, metal ions, redox species and it displays a good reversibility. Moreover, glass TLC plates coated with probe 1 can readily detect acid vapors at an ambient atmosphere.

An o-hydroxyl aldehyde structure based naphthalimide derivative: Reversible photochromic properties and its application in ClO? detection in living cells

A bifunctional organic compound 2-butyl-6-hydroxy-1,3-dioxo-2,3-dihydro-1H-benzo[de] isoquinoline-5-carbaldehyde (BHC) with photochromic properties in solid state and probe detection for ClO? in complete water solution was synthesized and fully characterized. A ‘white–yellow–white’ reversible photochromic behavior could be observed when alternating UV/vis light irradiation on the solid BHC powder. Good fatigue resistance and adjustable bleaching rate were shown when heating conditions changes. In addition, BHC displayed a high selectivity and low detection limit (1.16 × 10?8 M) for ClO?. The photoluminescent fluorescence “on-off” recognition result can be easily identified and BHC has been tested for safely imaging living cells and detecting hypochlorite anion in vitro and vivo. A better water solubility of BHC effectively reduces damage caused by organic solvent in cell imaging progress.

A highly selective fluorescent probe based on Michael addition for fast detection of hydrogen sulfide

A new 4-hydroxy-1,8-naphthalimide-based compound (probe 1) has been designed and synthesized. The colorimetric and fluorescent properties of probe 1 towards hydrogen sulfide (H2S) were investigated in detail. The results show that the probe 1 c

A novel flavin derivative reveals the impact of glucose on oxidative stress in adipocytes

We present the synthesis and characterisation of naphthalimide-flavin redox sensor 1 (NpFR1), a novel flavin molecule that is almost non-fluorescent in reduced form, but oxidation gives rise to a 125-fold increase in fluorescence. Confocal microscopy experiments confirm that NpFR1 is sensitive to redox changes within living cells. This journal is the Partner Organisations 2014.

Controlling photophysics of styrylnaphthalimides through TICT, fluorescence and: E, Z -photoisomerization interplay

The photophysical properties of naphthalimide dyes NI1-3 with electron releasing 4-methoxy- (NI1), 3,4-dimethoxystyryl- (NI2) and dimethylaminostyryl (NI3) groups are examined in a variety of protic and aprotic solvents. All compounds demonstrate positive solvatochromism in the steady-state absorption and fluorescence spectra. The analysis of the dependence of the Stokes shift on the polarity of the solvent using the Lippert-Mataga equation allowed us to determine the change in the dipole moment upon excitation. The obtained data correspond to the formation of highly polar charge transfer states. Based on the transient absorption spectra and time-resolved fluorescence measurements, the presence of two different emissive states was definitely proved. The primarily formed planar Local Excited (LE) state dominates in non-polar solvents like cyclohexane and toluene where it relaxes mostly through fluorescence and E,Z-isomerisation pathways. In polar solvents, an alternative relaxation channel emerges that consists of twisting around single bond between styryl and naphthalimide fragments, which leads to the formation of a Twisted Intramolecular Charge Transfer (TICT) state. The factors affecting the fluorescence of TICT states are discussed. The observed spectral effects are rationalized using quantum-chemical calculations, X-ray data and NMR spectroscopy.

A highly selective colorimetric and ratiometric fluorescent chemodosimeter for detection of fluoride ions based on 1,8-naphthalimide derivatives

A high selective colorimetric and ratiometric fluorescent probe based on 4-hydroxy-1, 8-naphthalimide was designed and synthesized to detect fluoride ions (F-). The sensing behavior of this probe was studied by UV-visible and fluorescence spect

A novel fluorescent molecule based on 1,8-naphthalimide: Synthesis, spectral properties, and application in cell imaging

A novel naphthalimide molecule, 4-(2-methoxyethoxy)-N-butyl-1,8- naphthalimide (MEBN), has been synthesized and characterized. The UV-visible absorption and fluorescence emission spectral properties in n-hexane, toluene, CHCl3, and CH3OH were studied. Its optical properties depend on solvent polarity. The application of MEBN in cell imaging was investigated.

UV and fluorescent spectra study the reaction between 1, 8-Naphthalimide derivative and hypochlorite their applications

Two simple, efficient turn-on fluorescent probes for hypochlorite have been rationally designed and developed by utilizing the oxidation of hypochlorite. Notably, probe 1 and 2 displayed rapid and remarkable turn-on responses to ClO? in PBS buffer solution (pH 7.4). Further, the optical properties of two probes and their ClO?-addition products were confirmed by density functional theory calculations. And detection limits of two probes for ClO? based on the definition by IUPAC were calculated for 2.882 nM and 0.354 μM. More importantly, cell imaging experiments demonstrated that probe 1 was more suitable for detecting the ClO? in living A549 cells. And both two probes had the possibility of potentially applied in practical applications such as detecting the hypochlorite concentration of tap water and river water.

Fluorescent photochromic donor-acceptor Stenhouse adduct controlled by visible light

A novel photochromic fluorescent DASA (donor-acceptor Stenhouse adduct) switch controlled by visible light was successfully designed and synthesized. Using 1,8-naphthalimide fluorophore in combination with indoline-based “donor” and barbituric acid “acceptor”, the DASA molecule exhibits two independent absorption bands at 440 nm and 616 nm. The physical and thermodynamic properties of fluorescent donor-acceptor Stenhouse adduct (DASA-NDI) have been investigated in different solvents. In accordance with the unique fluorescent properties under visible light/heat and H+/Cu2+, using fluorescence intensity at 604 nm (I604) as an output and visible light, H+ and Cu2+ as inputs, a combinatorial logic gate consisting of NOR and AND logics can be described and operated.

A novel ratiometric fluorescent probe based on 1, 8-naphthalimide for the detection of Ho3 + and its bioimaging

A ratiometric fluorescent probe for the detection of Ho3 + in DMSO-aqueous medium was designed and synthesized based on 1, 8-naphthalimide. The probe displayed response to Ho3 + with a fluorescence decrease at 512 nm and enhancement at 480 nm, accompanying with a distinct fluorescence change from bright yellow-green to cyan. Besides, the probe exhibited a lower detection limit (6 × 10? 8 M) and could be used in intracellular fluorescence imaging. To the best of the knowledge, it was the first ratiometric fluorescent probe for Ho3 + detection. This probe was expected to be a useful tool for further elucidating the roles of Ho3 + in materials, biology and environment.

Four-, five- and six-coordinated transition metal complexes based on naphthalimide Schiff base ligands: Synthesis, crystal structure and properties

Two bidentate Schiff base ligands (HL1?=?N-n-butyl-4-[(E)-2-(((2-aminoethyl)imino)methyl)phenol]-1,8-naphthalimide; and HL2?=?N-n-butyl-4-[(E)-2-(((2-aminoethyl)imino)methyl)-6-methoxyphenol]-1,8-naphthalimide) with their metal complexes [Cu(L1)2] (1), [Zn(L1)2(Py)]2?H2O (2) and [Ni(L2)2(DMF)2] (3) have been synthesized and characterized. Single-crystal X-ray structure analysis reveals that complex 1 has a four-coordinated square geometry, while complex 2 is a five-coordinated square pyramidal structure and complex 3 is a distorted six-coordinated octahedral structure. Cyclic voltammograms of 1 indicate an irreversible Cu2+/Cu+ couple. In vitro antioxidant activity assay demonstrates that the ligands and the two complexes 1 and 3 display high scavenging activity against hydroxyl (HO?) and superoxide (O2 ??) radicals. Moreover, the fluorescence properties of the ligands and complexes 1–3 were studied in the solid state. Metal-mediated enhancement is observed in 2, whereas metal-mediated fluorescence quenching occurs with 1 and 3.

A Water-Soluble, Two-Photon Probe for Imaging Endogenous Hypochlorous Acid in Live Tissue

Detection of hypochlorous acid (HClO) in the living system may help to uncover its essential biological functions. However, current imaging agents suffer from poor water solubility that limit their live-tissue applications. Here, a water-soluble probe (NNH) is devised through innovative hydrazone modification of 1,8-naphthalimide at 3′ position. NNH was successfully applied to tracking endogenous HClO in both cultured macrophages and a liver injury model in mice. NNH demonstrated remarkably increased water solubility and multiple desirable features including two-photon absorbance, anti-bleaching capability, rapid cellular uptake, and low cytotoxicity. NNH is the first hydrazone-based probe for real-time imaging of HClO in live tissue.

A 4-hydroxynaphthalimide-derived ratiometric fluorescent chemodosimeter for imaging palladium in living cells

A highly selective ratiometric fluorescent chemodosimeter derived from 4-hydroxynaphthalimide was designed and synthesized to image palladium species in living cells by virtue of a palladium-catalyzed depropargylation reaction, and it could monitor three typical palladium species (0, + 2 and + 4) without additional reagents. The Royal Society of Chemistry 2011.

Identification and Isolation of Glucosytransferases (GT) Expressed Fungi Using a Two-Photon Ratiometric Fluorescent Probe Activated by GT

As is well-known, fungi are an important biocatalysis model of glucosylation and have been widely applied for bioactive compounds glucosylation mediated by the intracellular glucosytransferases (GTs). However, there is no efficient method for the real-time detection of GTs and the rapid isolation of the target fungi strains with the high expression of GTs. In the present work, we first developed a two-photon ratiometric fluorescent probe N-(n-butyl)-4-hydroxy-1,8-naphthalimide (NHN) for detecting the glucosyltransferases activity and intracellular imaging of GTs. Under UV light (365 nm), the transformed product of NHN mediated by intracellular glucosyltransferase displayed blue emission to guide the rapid isolation of fungal strains possessing overexpression of GTs from complex soil samples. Finally, by using the fluorescent probe, two target fungi were isolated and identified to be Rhizopus oryzae and Mucor circinelloides by molecular analysis, and they exhibited a robust capability for regio- and stereospecific O-glycosylation. Our results fully demonstrated that NHN may be a promising tool for guiding real-time GTs activity in fungal strains and even for developing natural fungal strains with GTs overexpression.

Colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

A colorimetric chemosensor TBS-NA, 4-(tert-butyldimethylsilyloxy)-N-butyl- naphthalimide was designed and synthesized. Addition of fluoride ion to a CH3CN solution of TBS-NA can result in an obvious color change (from colorless to yellow) and UV-Vis absorption spectral change in a short time. This indicated that TBS-NA had highly selectivity for fluoride detection over other anions, such as Cl-, Br-, I-, HSO4-, ClO4- and AcO- in CH3CN solutions, and the selectively detection was due to the selective cleavage of Si-O bond in TBS-NA by fluoride. The detection limit was calculated to be 0.59 μM.

A naphthimide-based ratiometric fluorescent probe for selective and visual detection of phosgene in solution and the gas phase

As a colorless, highly toxic and widely used chemical reagent, phosgene poses a potentially serious threat to public health and environmental safety. Therefore, there is an urgent need to develop a simple and sensitive method for detecting phosgene. In this work, a ratiometric fluorescent probe (NED) for phosgene was developed by utilizing 4-substituted 1,8-naphthimide unit as the fluorophore and ethylenediamine as the recognition moiety. The probe NED undergoes intramolecular cyclization reaction with phosgene, resulting in a remarkable ratiometric fluorescence response. The probe NED displays high sensitivity (LOD = 4.9 nM), excellent ratiometric fluorescence signal, and high selectivity toward phosgene over other relevant analytes. In addition, paper test strip capable of visually detecting gaseous phosgene has also been fabricated.

Piperazine-bridged naphthalimide aminothiazole oxime compound as well as preparation method and application thereof

The invention relates to piperazine bridged naphthalimide aminothiazole oxime compounds as well as a preparation method and application thereof, and belongs to the technical field of chemical synthesis. The piperazine-bridged naphthalimide aminothiazole oxime compound is shown as a general formula I, has certain inhibitory activity on one or more of gram-positive bacteria, gram-negative bacteria and fungi, and can be used for preparing antibacterial and/or antifungal drugs, so that more efficient and safe candidate drugs are provided for clinical antimicrobial treatment, and the clinical treatment problems of increasingly serious drug resistance, stubborn pathogenic microorganisms, newly appearing harmful microorganisms and the like are favorably solved. The preparation raw materials are simple, cheap and easy to obtain, the synthetic route is short, and the method has important significance in anti-infection application.

An HDAC8-selective fluorescent probe for imaging in living tumor cell lines and tissue slices

Histone deacetylase 8 (HDAC8) has been used as a therapeutic target for many cancers as it is highly expressed in neuroblastoma cells and breast cancer cells. HDAC8-selective fluorescent probes need to be urgently developed. Herein, two novel fluorescent probes, namelyNP-C6-PCIandAM-C6-PCI, based on the conjugation of 1,8-naphthalimide with a highly selective inhibitor of HDAC8 (PCI-34051) were reported. Compared withPCI-34051(KD= 6.25 × 10?5M),NP-C6-PCI(KD= 8.05 × 10?6M) andAM-C6-PCI(KD= 7.42 × 10?6M) showed great selectivity toward HDAC8. Two fluorescent probes exhibited high fluorescence intensity underλex= 450 nm and a large Stokes shift (100 nm).NP-C6-PCIwas selected for cell and tissue imaging due to the similarity in the bioactivity ofNP-C6-PCIwithPCI-34051. The ability ofNP-C6-PCIto target imaging HDAC8 in SH-SY5Y and MDA-MB-231 tumor cells was demonstrated. Furthermore,NP-C6-PCIwas applied to imaging SH-SY5Y tumor tissue slices to indicate the relative expression level of HDAC8. Therefore, this HDAC8-selective fluorescent probe can be expected for applications in HDAC8-targeted drug screening as well as in pathologic diagnoses.