25981-83-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloro-2,3,3-trimethyl-3H-indole is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications, contributing to the advancement of medicine.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Chloro-2,3,3-trimethyl-3H-indole serves as a building block for the creation of agrochemicals. Its incorporation into these compounds can enhance their effectiveness in agricultural applications, such as pest control and crop protection.
Used in Organic Chemistry:
5-Chloro-2,3,3-trimethyl-3H-indole is utilized as a versatile intermediate in organic chemistry for the synthesis of a wide range of organic compounds. Its reactivity and structural features make it a valuable component in the development of new chemical entities with diverse applications.

InChI:InChI=1/C11H12ClN/c1-7-11(2,3)9-6-8(12)4-5-10(9)13-7/h4-6H,1-3H3

Upstream product

• 55476-05-6 3-(4-chlorophenyl)-5,5-dimethyl-4-methylidene-2-oxooxazolidine 
• 563-80-4 3-methyl-butan-2-one 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 4437-80-3 4,4-dimethyl-5-methylene-1,3-dioxolan-2-one 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 380632-86-0 2-chloro-7-ethyl-8-hydroxy-10,10-dimethyl-10H-pyrido[1,2-a]indol-6-one 
• 380634-71-9 2-chloro-8-hydroxy-7,10,10-trimethyl-10H-pyrido[1,2-a]indol-6-one 
• 6872-17-9 5-chloro-1,3,3-trimethyl-2-methyleneindoline 
• 380632-04-2 7-acetyl-2-chloro-8-hydroxy-10,10-dimethyl-10H-pyrido[1,2-a]indol-6-one 
• 465540-77-6 2,7,9-trichloro-10,10-dimethyl-7-phenyl-10H-pyrido[1,2-a]indole-6,8(7H)-dione 

Relevant academic research and scientific papers

Synthesis, characterization and cytotoxic activity of new indole schiff bases, derived from 2-(5-chloro-3,3-dimethyl-1,3-dihydro-indol-2-ylidene)-malonaldehyde with substituted aniline

Series of new compounds of indole Schiff base derivatives have been synthesized by reaction of 2-(5-Chloro-3,3-dimethyl-1,3-dihydro-indol-2-ylidene)-malonaldehyde with aniline substituted. The chemical structures of the synthesized compounds were characte

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.

Ultrabright and Serum-Stable Squaraine Dyes

Highly stable symmetric and asymmetric squaraine fluorophores have been synthesized featuring an internal salt bridge between a quaternary ammonium cation and the central oxycyclobutenolate ring of the chromophore. Some of our newly synthesized symmetric and asymmetric compounds display increased molar absorptivity, quantum yield in serum, and thermal/photochemical stability over previously reported squaraine-based dyes. Consequently, both classes show great promise in resurfacing the normal environment-labile squaraine dyes as novel imaging agents and scaffolds for fluorescence sensing. Furthermore, incorporating a covalent attachment point away from the conjugated system allows for biological tagging applications without disturbing the optimum optical characteristics of the newly designed fluorophore.

Second Generation G-Quadruplex Stabilizing Trimethine Cyanines

G-Quadruplex DNA has been recognized as a highly appealing target for the development of new selective chemotherapeutics, which could result in markedly reduced toxicity toward normal cells. In particular, the cyanine dyes that bind selectively to G-quadruplex structures without targeting duplex DNA have attracted attention due to their high amenability to structural modifications that allows fine-tuning of their biomolecular interactions. We have previously reported pentamethine and symmetric trimethine cyanines designed to effectively bind G-quadruplexes through end stacking interactions. Herein, we are reporting a second generation of drug candidates, the asymmetric trimethine cyanines. These have been synthesized and evaluated for their quadruplex binding properties. Incorporating a benz[c,d]indolenine heterocyclic unit increased overall quadruplex binding, and elongating the alkyl length increases the quadruplex-to-duplex binding specificity.

Iodine-Promoted Domino Oxidative Cyclization for the One-Pot Synthesis of Novel Fused Four-Ring Quinoxaline Fluorophores by sp3 C?H Functionalization

A method for the synthesis of novel fused four-ring quinoxaline skeleton has been described by an I2 promoted sp3 C?H functionalization between 1,2,3,3-tetramethyl-3H-indolium iodides and 1,2-diamines. This transformation proceeds smoothly under metal- and peroxide-free conditions through a sequential iodination, oxidation, annulation and rearrangement. Moreover, 8,9-dichloro-5,12,12-trimethyl-2-(trifluoromethyl)-5,12-dihydroquinolino[2,3-b]quinoxaline showed good photophysical properties and was used in live cell imaging, indicating the potential value of this skeleton as a fluorophore in probes.

Synthesis and optical properties of near-infrared meso-phenyl-substituted symmetric heptamethine cyanine dyes

Heptamethine cyanine dyes are a class of near infrared fluorescence (NIRF) probes of great interest in bioanalytical and imaging applications due to their modifiability, allowing them to be tailored for particular applications. Generally, modifications at the meso-position of these dyes are achieved through Suzuki-Miyaura C-C coupling and SRN1 nucleophilic substitution of the chlorine atom at the meso-position of the dye. Herein, a series of 15 meso phenyl-substituted heptamethine cyanines was synthesized utilizing a modified dianil linker. Their optical properties, including molar absorptivity, fluorescence, Stokes shift, and quantum yield were measured. The HSA binding affinities of two representative compounds were measured and compared to that of a series of trimethine cyanines previously synthesized by our lab. The results indicate that the binding of these compounds to HSA is not only dependent on hydrophobicity, but may also be dependent on steric interferences in the binding site and structural dynamics of the NIRF compounds.

YELLOW METHINE DYES

The present invention relates to novel methine dyes, methods for the preparation thereof and use thereof for dyeing plastics, especially polyamides, so as to obtain yellow colorings with improved light fastness and improved thermostability.

Benz[c,d]indolium-containing monomethine cyanine dyes: Synthesis and photophysical properties

Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.

Near-Infrared Illumination of Native Tissues for Image-Guided Surgery

Our initial efforts to prepare tissue-specific near-infrared (NIR) fluorescent compounds generated successful correlation between physicochemical properties and global uptake in major organs after systemic circulation and biodistribution. Herein, we focus on the effects on biodistribution based on modulating electronic influencing moieties from donating to withdrawing moieties at both the heterocyclic site and through meso-substitution of pentamethine cyanine fluorophores. These selected modifications harnessed innate biodistribution pathways through the structure-inherent targeting, resulting in effective imaging of the adrenal glands, pituitary gland, lymph nodes, pancreas, and thyroid and salivary glands. These native-tissue contrast agents will arm surgeons with a powerful and versatile arsenal for intraoperative NIR imaging in real time.