3484-22-8

Basic information

• Product Name: 5-Nitro-2,3,3-trimethylindolenine
• Synonyms: 5-NITRO-2,3,3-TRIMETHYLINDOLENINE;2,3,3-TRIMETHYL-5-NITRO-3H-INDOLE;2,3,3-trimethyl-5-nitro-3h-indol;5-NITRO-2,3,3-TRIMETHYLINDOLE;5-NITRO-2.3.3-TRIMETHYLINDOLENINE HPLC 98.0% YELLOW CRYSTALS OR CRYSTALLINE POWDER;5-Nitro-2,3,3-trimethylindoleninez;2,3,3-trimethyl-5-nitroindole;2,3,3-trimethyl-5-nitro-indole
• CAS NO: 3484-22-8
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.23
• EINECS: 1806241-263-5
• Product Categories: Heterocycle-Indole series
• Mol File: 3484-22-8.mol

Chemical Properties

• Melting Point: 130-131 °C(Solv: ethanol (64-17-5))
• Boiling Point: 315.7ºC at 760 mmHg
• Flash Point: 144.7 ºC
• Appearance: Crystals or crystalline powder
• Density: 1.23 g/cm³
• Vapor Pressure: 0.000798mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: 2-8°C
• PKA: 3.17±0.40(Predicted)
• CAS DataBase Reference: 5-Nitro-2,3,3-trimethylindolenine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitro-2,3,3-trimethylindolenine(3484-22-8)
• EPA Substance Registry System: 5-Nitro-2,3,3-trimethylindolenine(3484-22-8)

Safety Data

• Hazardous Substances Data: 3484-22-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-Nitro-2,3,3-trimethylindolenine is used as a reactant in the synthesis of various organic compounds, serving as a key intermediate for the production of a range of chemical products.
Used in Dye and Pigment Production:
In the dye and pigment industry, 5-Nitro-2,3,3-trimethylindolenine is used as a precursor for the synthesis of dyes and pigments, contributing to the development of colorants for different applications.
Used in Pharmaceutical Industry:
5-Nitro-2,3,3-trimethylindolenine is used as a precursor in the pharmaceutical industry for the synthesis of various medicinal compounds, playing a crucial role in the development of new drugs.
Safety Considerations:
Due to the presence of a nitro group, 5-Nitro-2,3,3-trimethylindolenine can be potentially explosive and hazardous to human health. It is essential to handle this chemical with care, adhering to proper safety protocols to minimize risks during its use in various applications.

InChI:InChI=1/C11H12N2O2/c1-7-11(2,3)9-6-8(13(14)15)4-5-10(9)12-7/h4-6H,1-3H3

Upstream product

• 1640-39-7 2,3,3-trimethylindoleniune 
• 563-80-4 3-methyl-butan-2-one 
• 100-16-3 4-nitrophenylhydrazone 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 3034-19-3 (2-nitrophenyl)hydrazine 
• 91337-77-8 3-methyl-butan-2-one-(4-nitro-phenylhydrazone) 

Downstream Products

• 140451-71-4 5-nitro-2,3,3-trimethylindolino(1,2-b)oxazoline 
• 64944-14-5 1,2,3,3-tetramethyl-5-nitro-3H-indol-1-ium iodide 
• 773-63-7 5-amino-2,3,3-trimethyl-3H-indole 
• 119374-54-8 1-ethyl-2,3,3-trimethyl-5-nitro-3H-indolium iodide 
• 119374-55-9 1-butyl-5-nitro-2,3,3-trimethylindolium iodide 
• 1458033-62-9 1'-ethyl-3',3'-dimethyl-5',6-dinitro-1',3,3',4-tetrahydrospiro[chromene-2,2'-indole] 
• 144723-41-1 1',3',3'-trimethyl-5',8-dinitrospiro[benzo[f]chromene-3,2'-indoline] 

Relevant articles and documents

Croconaine rotaxane for acid activated photothermal heating and ratiometric photoacoustic imaging of acidic pH

Absorption of 808 nm laser light by liposomes containing a pH sensitive, near-infrared croconaine rotaxane dye increases dramatically in weak acid. A stealth liposome composition permits acid activated, photothermal heating and also acts as an effective nanoparticle probe for ratiometric photoacoustic imaging of acidic pH in deep sample locations, including a living mouse.

Synthesis, characterization, and UV–visible study of some new photochromic formyl-containing 1′,3′,3′-trimethylspiro[chromene-2,2′-indoline] derivatives

The spiropyran derivatives can exist in two forms, the closed-ring spiropyran form and the open-ring merocyanine (MC) form. The SP form could be converted into the MC form upon UV irradiation. In this work, some 1′,3′,3′-trimethylspiro[chromene-2,2′-indoline] derivatives containing the nitro and formyl groups are synthesized via the reaction of 1,3,3-trimethyl-2-methylene-5-nitroindoline with the corresponding salicylaldehyde derivatives. These compounds have different photochromic behaviors. The synthesized photochromic molecules are characterized by the FT-IR, 1H-NMR, and 13C-NMR spectroscopic techniques. In order to investigate the photochromic properties of these compounds, the UV–visible spectroscopic analyses of their methanolic solutions before and after exposure to a UV lamp (in the spectral range of 360–400?nm) are studied. Graphic abstract: [Figure not available: see fulltext.].

PH reversible activation type photo-thermal/photodynamic/fluorescent integrated probe molecule

The invention discloses a pH reversible activation type photo-thermal/photodynamic/fluorescent integrated probe molecule, and belongs to the technical field of biological medicines. A pH-responsive asymmetric cyanine structure is used as a core unit, and through structural modification and introduction of halogen and other heavy atoms into a conjugated system, a photo-thermal/photodynamic/fluorescent integrated probe molecule capable of being specifically activated by a tumor weakly acidic microenvironment is constructed. The photo-thermal/photodynamic/fluorescent integrated probe has good stability, a good photo-thermal effect and excellent active oxygen generation capacity, and has huge potential in tumor treatment.

Heptamethine nitroindole cyanine dye, preparation method and application thereof

The invention discloses a heptamethine nitro indocyanine dye, a preparation method and application thereof, and belongs to the field of polymethine indocyanine dyes and preparation thereof, wherein the structural formula of the heptamethine nitro indocyanine dye is represented by a formula (I). The preparation method comprises the following steps: 1) carrying out a heating reaction on raw materials containing a 2,3,3-trimethyl-nitroindole derivative and a nucleophilic substituted compound under a vacuum condition to obtain an organic ammonium salt; and 2) carrying out a heating reaction on a solution containing the organic ammonium salt obtained in the step 1) and a cycloalkene derivative under a closed condition. The dye has near-infrared light absorption and fluorescence development properties, and can be used as a probe auxiliary agent; and the preparation method has the advantages of short synthesis route, environment-friendly solvent, simple process, avoidance of noble metal catalysis, high yield, high purity and the like, is high in applicability, and can be used for synthesizing products of various structure types.

Effects of Substituents on Metastable-State Photoacids: Design, Synthesis, and Evaluation of their Photochemical Properties

Recently, metastable-state photoacids have been widely used to control proton transfer in numerous chemical and biological processes as well as applications with visible light. Generally, substituents have a great influence on the photochemical properties of molecules, which will further affect their applications. Yet, the effects of substituents on metastable-state photoacids have not been studied systematically. In this work, 16 metastable-state photoacid derivatives were designed and synthesized on the basis of substituents having a large range of σ–π electron–donor–acceptor capabilities. The effects of substituents on the color display [or maximum absorption band(s)], solubility, pKa values, dark/photoacidity, photosensitivity, and relaxation kinetic(s) were investigated in detail. This study will be helpful for the targeted design and synthesis of promising photoacids and the application of their photocontrolled proton-release processes in functional materials/devices.

A highly sensitive fluorescent probe that quantifies transthyretin in human plasma as an early diagnostic tool of Alzheimer's disease

The development of sensitive and reliable fluorescent probes for the early diagnosis of Alzheimer's disease (AD) is highly challenging and plays an important role in achieving effective treatments. Herein, we designed and synthesized an indole-based fluorophore for TTR in human plasma, an important hallmark of AD pathogenesis. This robust and simple fluorescent method allows quantification of TTR in the complex biological matrix.

Analysis of Bisulfite Via a Nitro Derivative of Cyanine-3 (NCy3) in the Microfluidic Channel

NCy3, a derivative of Cyanine 3 with a nitro substituent, showed a high reactivity to bisulfite in aqueous media, instantly leading to ratiometric change of absorption spectra and significant fluorescence quenching. Applied in the microfluidic channel, NCy3 functionalize as a sensitive approach for quantitative detection of bisulfite, particularly for samples with a small volume.

Photooxidation of oxazolidine molecular switches: Uncovering an intramolecular ionization facilitated cyclization process

Photooxidation of oxazoline (OXA) molecular switches through media-induced intramolecular ionization is reported. The formation of the photooxidation product occurs by attack of the flexible donor group (-CH2CH2OH) to the adjacent CC with 1O2 as the oxidant. The novel seven-membered ring sub-structure of the photooxidation product was inferred by HRMS, IR and 1H NMR spectroscopy. Additionally, acid released from solvent photolysis was found to affect the product formation and efficiency of the photooxidation.

Two near-infrared highly sensitive cyanine fluorescent probes for pH monitoring

Two near-infrared (NIR) pH-activated heptamethine indocyanine probes with quaternary ammonium unit were designed and synthesized. The absorption and emission titrations indicate that cationic structure improves the cyanine dye's aqueous solubility and these two probes exhibit highly sensitive response to pH in acid condition. Their fluorescence intensities both gradually increase about 25-fold from pH 7.60 to 3.00 with pKa values of 4.72 and 4.45 respectively, which are suitable for studying acidic organelles in living cells. Moreover, their fluorescence intensities are linearly proportional to pH values in the range of 5.50–4.00. These results are probably attributed to the protonation of the indole nitrogen atoms, which are verified by 1H NMR spectra. Furthermore, these two probes can achieve real-time imaging of cellular pH and detection of pH in situ in living HeLa cells due to their excellent properties, including good reversibility, desirable photostability, high selectivity, low cytotoxicity and remarkable membrane permeability.

Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines

Spiropyrans and spirooxazines represent an important class of photochromic compounds with a wide variety of applications. In order to effectively utilize and design these photoswitches it is desirable to understand how the substituents affect photochromic properties, and how the different structural motifs compare under identical conditions. In this work a small library of photoswitches was synthesized in order to comparatively evaluate the effect of substituent modifications and structure on photochromism. The library was designed to modify positions that were believed to have the greatest effect on C-O bond lability and therefore the photochromic properties. Herein we report a comparative analysis of the UV and visible light responses of 30 spiropyrans, spiroindolinonaphthopyrans, and spirooxazines. The influence of gadolinium(III) binding was also investigated on the library of compounds to determine its effect on photoswitching. Both assays demonstrated different trends in substituent and structural requirements for optimal photochromism.