54136-24-2

Usage

Uses

Used in Organic Synthesis:
2,3,3-Trimethyl-5-bromo-3H-indole is used as a building block in organic synthesis for its ability to contribute to the creation of complex organic molecules. Its unique structure allows for versatile chemical reactions, facilitating the synthesis of a wide range of compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2,3,3-Trimethyl-5-bromo-3H-indole is utilized as a key component in drug discovery and development. Its reactivity and structural features make it a promising candidate for the design of new drugs with potential therapeutic applications.
Used in Agrochemical Development:
2,3,3-Trimethyl-5-bromo-3H-indole also finds application in the agrochemical sector, where it is employed in the research and development of new pesticides and other agricultural chemicals. Its unique chemical properties can contribute to the creation of effective and environmentally friendly products.
Used in Dye and Pigment Manufacturing:
2,3,3-TRIMETHYL-5-BROMO-3H-INDOLE is also used in the manufacturing of dyes, pigments, and other fine chemicals due to its ability to impart color and stability to various products. Its chemical structure allows for the production of a diverse array of colorants for different applications.
Safety Precautions:

Upstream product

• 64-19-7 acetic acid 
• 78-93-3 butanone 
• 589-21-9 (4-bromophenyl)hydrazine 
• 563-80-4 3-methyl-butan-2-one 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 41931-18-4 (4-bromophenyl)hydrazine hydrochloride salt 

Downstream Products

• 1361598-44-8 N,N-bis(4-methoxyphenyl)-2,3,3-trimethyl-3H-indol-5-amine 
• 1381967-98-1 5-bromo-1-(3,7-dimethyloctyl)-2,3,3-trimethyl-3H-indol-1-ium tosylate 
• 1400770-53-7 C₅₃H₅₃N₃O₄ 
• 1417649-66-1 C₅₈H₆₁N₃O₆ 
• 1400770-56-0 C₅₀H₄₅N₃O₆ 
• 1607805-36-6 C₂₇H₃₀N₂ 
• 1607805-37-7 C₂₇H₃₀N₂O₂ 
• 1607805-38-8 C₃₇H₅₀N₂O₂ 

Relevant academic research and scientific papers

Indoline and benzothiazole-based squaraine dye-sensitized solar cells containing bis-pendent sulfonate groups: Synthesis, characterization and solar cell performance

Two new symmetric squaraine sensitizers (SQTHZ and SQIND) carrying benzothiazole and indoline moieties as strong electron donating groups to inject the electron into the TiO2 nanoparticles were tested as DSSC. The theoretical calculations and absorption results show that the electron density of LUMO of SQTHZ is delocalized in the whole chromophore, leading to strong electronic coupling between SQTHZ sensitizer and the conduction band of TiO2. Furthermore, the presence of long alkyl chain with pendent bis-SO3 - groups would inhibit recombination and decrease the dye aggregation. Interestingly, SQTHZ displayed UV–Vis and NIR absorption at a longer wavelength compared to SQIND. This structure feature, as well as optical properties, would lead to improved efficiency of dye-sensitized solar cell with overall better photovoltaic performance (η of 3.31%, Jsc of 7.65 mA/cm2, Voc of 0.59, ff of 0.71 and IPCE of 47% at 674 nm) compared to SQIND.

Synthesis and acid-responsiveness of an insulated π-conjugated polymer containing spiropyrans in its backbone

A π-conjugated polymer containing spiropyrans (SPs), which could be almost completely converted to protonated merocyanines (MCH+) and back to the SP form by adding an acid and a base, respectively, was developed. The insulation of the π-conjugated polymer, referred to as insulated spiropyran-containing poly(p-phenylene ethynylene) (ins-SP-PPE), using permethylated α-cyclodextrins (PM α-CD) suppressed the π-π interaction between the polymer chains containing MCH+, and the installation of PM α-CD improved the switching ability of SPs. The polymer exhibited repeatable acidochromism with almost complete conversion between the SP and MCH+ forms. Photoluminescence measurements were conducted and the acid-induced luminescence quenching of the polymer in the solution was observed, which stemmed from energy transfer from the PPE to MCH+ moieties. In the solid state, the quantum yield of ins-SP-PPE was more than twice that of the uninsulated polymer, which derived from the insulation effects. The acid-induced luminescence quenching was also observed in the solid state.

Ferrocene-modified bis(spiropyridopyran)s as synthetic signaling receptors for guanine-guanine dinucleoside derivatives

A ferrocene-linked bis(spiropyridopyran) was designed and synthesized, that recognized guanine-guanine dinucleoside derivatives via complementary hydrogen bonds in CH2Cl2, resulting in the isomerization of the colorless spiropyridopyran as self-indicating receptors.

Systematic variation of thiophene substituents in photochromic spiropyrans

Spiropyrans are notable among different classes of photochromic compounds due to their large structural and electronic transformation upon isomerization. In order to parlay the electronic differences associated with the two isomeric forms into a materials based switch, the spiropyran ultimately requires a covalent attachment through a conjugated pathway. In this work a synthetic method was developed to incorporate spiropyran (SP) into thiophene based materials. A series of compounds with a systematic variation of substituents were synthesized (SP-T, SP-T-Br, SP-T-T, SP-T-T-T and SP-T-T-T-T-SP) and their photochromism in both polar (methanol) and non-polar (toluene) solvents were studied. These compounds showed a systematic variation of photochromic properties.

Synthesis of novel thermally reversible photochromic axially chiral spirooxazines

(Equation Presented). The Suzuki reactions of diboronic acid 1 and bromo-spirooxazine 2, under N2 atmosphere and aerobic conditions, gave the dispirooxazine-substituted binaphthyl product 3 and the monospirooxazine-substituted binaphthyl derivative 4, respectively. The thermally reversible photochromic behavior of the target axially chiral spirooxazines 3 was investigated, and both the ring-opening process upon irradiation with 365 nm light and the thermally reverse ring-closing process were fast. These chiral spirooxazines were found to impart their chirality to an achiral liquid crystal host, at low doping levels, to form a self-organized photoresponsive helical superstructure.

A pH reversibly activatable NIR photothermal/photodynamic-in-one agent integrated with renewable nanoimplants for image-guided precision phototherapy

Phototherapy has great potential to revolutionize conventional therapeutic modalities. However, most phototherapeutic strategies based on multicomponent therapeutic agents generally lack tumor-specificity, resulting in asynchronous therapy and superimposed side-effects. Severe heat damage is also inevitable because of the necessity of continuous external irradiation. Here we show the design of an acid-activated and continuous external irradiation-free photothermal and photodynamic (PTT/PDT) synchronous theranostic nanoplatform for precision tumor-targeting near-infrared (NIR) image-guided therapy. pH-reversibly responsive brominated asymmetric cyanine is designed as the tumor-specific NIR PTT/PDT-in-one agent to enhance anticancer efficiency and reduce side-effects. Ultra-small NIR persistent luminescence nanoparticles are prepared as both the imaging unit and renewable nanoimplant. Biotin functionalized polyethylene glycol is introduced to endow active tumor-targeting ability and prolong blood-circulation. The developed smart platform offers merits of reversible activation, PTT/PDT synergetic enhancement, tumor targetability and continuous external irradiation-free properties, allowing autofluorescence-free image-guided phototherapy only in tumor sites. This work paves the way to developing smart theranostic nanoplatforms for precision medicine.

Novel hemicyanine sensitizers based on benzothiazole-indole for dye-sensitized solar cells: Synthesis, optoelectrical characterization and efficiency of solar cell

Synthesis, characterization, and photovoltaic properties of three new hemicyanine sensitizers based benzothiazole-indoline (HC-TH, HC-IND1 and HC-IND2) were tested in DSSC with TiO2 film. These sensitizers have a higher molar absorption coefficient, and thus have better light harvesting properties. Electrochemical, theoretical, and spectroscopic methods were used to calculate energy levels of the dye molecules both in the excited state and in the ground state. The results obtained from the spectroscopy and Tafel studies show a marked increase in overall photoelectro-chemical cell output with Br-substitute at p-position in the hemicyanine sensitizer. Interestingly, HC-IND2 showed absorption of UV–Vis at a longer wavelength than HC-IND1 and HC-TH. This structural feature, as well as optical properties, would result in an improved efficiency of DSSC with a better photovoltaic output (4.01percent) solar to electricity conversion efficiency compared to HC-IND1 and HC-TH.

Halogenated cyanine dyes for synergistic photodynamic and photothermal therapy

Cyanine dyes are widely used in the field of tumor phototherapy due to their excellent photophysical properties. To explore the heavy atoms effects on the photothermal and photodynamic performance of phototherapeutic agents, chlorine, bromine, and iodine were introduced to synthesize a series of cyanine dyes (IR6, IR7, and IR8). We have found that all halogenated cyanine dyes exhibited high excitation wavelength (around 800 nm) and low dark toxicity. Among them, IR8 behaved the best singlet oxygen production ability in the three dyes. For photothermal performance, IR8 exhibited the best photothermal conversion rate (46.6%), photothermal stability, and excellent therapy efficiency (half-maximal inhibitory concentration, IC50 = 16.2 μg/mL). IR7 behaved a greater enhancement of the photothermal conversion rate (43.4%) than IR6 (42.3%). In conclusion, the heavy atoms effects on the photothermal and photodynamic properties of cyanine dyes are positively correlated with the increase of the atomic number of the halogen atom, and the iodine atom may be the most worthy of consideration in the all halogen atoms.

Near-Infrared Heptamethine Cyanine Dyes for Nanoparticle-Based Photoacoustic Imaging and Photothermal Therapy

We have synthesized and characterized a library of near-infrared (NIR) heptamethine cyanine dyes for biomedical application as photoacoustic imaging and photothermal agents. These hydrophobic dyes were incorporated into a polymer-based nanoparticle system to provide aqueous solubility and protection of the photophysical properties of each dye scaffold. Among those heptamethine cyanine dyes analyzed, 13 compounds within the nontoxic polymeric nanoparticles have been selected to exemplify structural relationships in terms of photostability, photoacoustic imaging, and photothermal behavior within the NIR (～650-850 nm) spectral region. The most contributing structural features observed in our dye design include hydrophobicity, rotatable bonds, heavy atom effects, and stability of the central cyclohexene ring within the dye core. The NIR agents developed within this project serve to elicit a structure-function relationship with emphasis on their photoacoustic and photothermal characteristics aiming at producing customizable NIR photoacoustic and photothermal tools for clinical use.

NARROW ABSORPTION POLYMER NANOPARTICLES AND RELATED METHODS

Polymers, monomers, narrow-band absorbing polymers, narrow-band absorbing monomers, absorbing units, polymer dots, and related methods are provided. Bright, luminescent polymer nanoparticles with narrow-band absorptions are provided. Methods for synthesizing absorbing monomers, methods for synthesizing the polymers, preparation methods for forming the polymer nanoparticles, and applications for using the polymer nanoparticles are also provided.