16650-14-9

Basic information

• Product Name: 1,3,3-TRIMETHYLINDOLINO-6'-BROMOBENZOPYRYLOSPIRAN
• Synonyms: 6-BROMO-1',3',3'-TRIMETHYLSPIRO[1(2H)-BENZOPYRAN-2,2'-INDOLINE];1,3,3-TRIMETHYLINDOLINO-6'-BROMOBENZOPYRYLOSPIRAN;Trimethylindolinobromobenzopyrylospiran;1,3,3-Trimethylindolino-6-bromobenzopyrylospirane;1,3,3-TRIMETHYLINDOLINO-6-BROMOBENZOPYRYLOSPIRAN [PHOTOCHROMIC COMPOUND] 98+%;1,3,3-Trimethylindolino-6'-bromobenzopyrylospiran [Photochromic Compound];1',3',3'-Trimethyl-6-bromospiro[2H-1-benzopyran-2,2'-indoline];1,3,3-Trimethyl-6'-bromospiro[indoline-2,2'-[2H-1]benzopyran]
• CAS NO: 16650-14-9
• Molecular Formula: C₁₉H₁₈BrNO
• Molecular Weight: 356.26
• Product Categories: Functional Materials;Photochromic Compounds;Spiropyrans (Photochromic)
• Mol File: 16650-14-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 450.8°C at 760 mmHg
• Flash Point: 226.5°C
• Appearance: /
• Density: 1.44g/cm³
• Vapor Pressure: 2.55E-08mmHg at 25°C
• Refractive Index: 1.68
• CAS DataBase Reference: 1,3,3-TRIMETHYLINDOLINO-6'-BROMOBENZOPYRYLOSPIRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,3-TRIMETHYLINDOLINO-6'-BROMOBENZOPYRYLOSPIRAN(16650-14-9)
• EPA Substance Registry System: 1,3,3-TRIMETHYLINDOLINO-6'-BROMOBENZOPYRYLOSPIRAN(16650-14-9)

Safety Data

• Hazardous Substances Data: 16650-14-9(Hazardous Substances Data)

Usage

General Description

1,3,3-TRIMETHYLINDOLINO-6'-BROMOBENZOPYRYLOSPIRAN is a chemical compound that belongs to the family of benzopyrans. It is a spiropyran derivative that contains a bromine atom and a 1,3,3-trimethylindolino group. 1,3,3-TRIMETHYLINDOLINO-6'-BROMOBENZOPYRYLOSPIRAN exhibits interesting photochromic properties, making it useful in the development of photochromic materials and optical switches. It can undergo reversible photoisomerization between the open and closed form in response to light, leading to changes in its color and absorption properties. This property has potential applications in the development of photoresponsive materials, sensors, and optical devices. Overall, 1,3,3-TRIMETHYLINDOLINO-6'-BROMOBENZOPYRYLOSPIRAN is a versatile compound with potential uses in photochromism and optoelectronics.

InChI:InChI=1/C19H18BrNO/c1-18(2)15-6-4-5-7-16(15)21(3)19(18)11-10-13-12-14(20)8-9-17(13)22-19/h4-12H,1-3H3

Upstream product

• 118-12-7 1,3,3-Trimethyl-2-methyleneindoline 
• 1761-61-1 5-bromosalicyclaldehyde 
• 5418-63-3 1,2,3,3-tetramethyl-3H-indolium iodide 

Relevant articles and documents

Observation of photochromic γ-cyclodextrin host-guest inclusion complexes

Substituted photochromic spiropyrans were included in γ-CD inclusion complexes and the photochromic behavior was monitored optically.

Direct Access by Mechanochemistry or Sonochemistry to Protonated Merocyanines: Components of a Four-State Molecular Switch

Direct access to the protonated merocyanine forms of two substituted spiropyrans by mechanosynthesis or sonochemistry was explored. The compounds were formed by the condensation reaction of the methyleneindolium iodide salt with salicylaldehyde derivatives. X-ray crystallography, 1H NMR spectroscopy, ab initio geometry optimization, and absorption spectroscopy were combined to provide a better understanding of the four-state molecular switch system in which the newly synthesized protonated merocyanines were found to play a central role. The results of this study suggest that the stability of the protonated merocyanines requires acidic conditions, as treatment with base led to the corresponding unprotonated merocyanines, which in turn spontaneously converted into photochromic closed spiropyrans.

Greener route for the synthesis of photo- and thermochromic spiropyrans using a highly efficient, reusable, and biocompatible choline hydroxide in an aqueous medium

Here, we report the synthesis of photo- and thermochromic spiropyrans promoted by a highly efficient, biocompatible, and reusable choline hydroxide (ChOH) in greener solvent water. This procedure provides several advantages such as simple workup, mild reaction conditions, short reaction time, and high yields of the products. Furthermore, the ChOH could be reused at least five times without significantly losing its catalytic activity. The structures of the synthesized spiropyran derivatives were confirmed by several characterization methods such as 1H NMR, 13C NMR, and mass spectra.