25981-83-3

Basic information

• Product Name: 5-Chloro-2,3,3-trimethyl-3H-indole
• Synonyms: AURORA KA-3417;2,3,3-TRIMETHYL-5-CHLORO-3H-INDOLE;2,3,3-TRIMETHYL-5-CHLORO-INDOLENINE;5-CHLORO-1,3,3-TRIMETHYL-2-METHYLENEINDOLINE;5-CHLORO-2,3-DIHYDRO-1,3,3-TRIMETHYL-2-METHYLENE-1H-INDOLE;5-CHLORO-2,3,3-TRIMETHYL-3H-INDOLE;5-CHLORO-2,3,3-TRIMETHYLINDOLE;5-CHLORO-2,3,3-TRIMETHYL-INDOLENINE
• CAS NO: 25981-83-3
• Molecular Formula: C₁₁H₁₂ClN
• Molecular Weight: 193.67
• EINECS: 247-387-4
• Product Categories: Halides;Pyrroles & Indoles;Indole;Pyrroles & Indoles;Heterocycle-Indole series;Heterocyclic Acids
• Mol File: 25981-83-3.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 271.1 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.083 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0109mmHg at 25°C
• Refractive Index: n20/D 1.594(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.87±0.40(Predicted)
• CAS DataBase Reference: 5-Chloro-2,3,3-trimethyl-3H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2,3,3-trimethyl-3H-indole(25981-83-3)
• EPA Substance Registry System: 5-Chloro-2,3,3-trimethyl-3H-indole(25981-83-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 25981-83-3(Hazardous Substances Data)

Usage

General Description

5-Chloro-2,3,3-trimethyl-3H-indole is a chemical compound with a molecular formula C11H11ClN. It is an organic compound that belongs to the class of indoles, which are heterocyclic compounds with a bicyclic structure containing a six-membered benzene ring fused to a five-membered pyrrole ring. This specific compound is characterized by the presence of a chlorine atom and three methyl groups attached to the indole ring. It is used in the pharmaceutical and agrochemical industries for the synthesis of various compounds and as a building block in organic chemistry. Its unique structure and chemical properties make it an important intermediate for the synthesis of biologically active compounds and materials.

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

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

Downstream Products

• 465540-70-9 2-chloro-8-hydroxy-10,10-dimethyl-7-phenyl-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 
• 465540-77-6 2,7,9-trichloro-10,10-dimethyl-7-phenyl-10H-pyrido[1,2-a]indole-6,8(7H)-dione 
• 227754-52-1 2-chloro-10,10-dimethyl-7-nitro-7-phenyl-10H-pyrido[1,2-a]indole-6,8(7H)-dione 

Relevant articles and documents

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

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.

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.