14238-53-0

Basic information

• Product Name: (4E)-3-hydroxy-2-[(Z)-(1,3,3-trimethylindol-2-ylidene)methyl]-4-[(1,3,3-trimethylindol-2-yl)methylidene]cyclobut-2-en-1-one
• Synonyms: (4E)-3-hydroxy-2-[(Z)-(1,3,3-trimethylindol-2-ylidene)methyl]-4-[(1,3,3-trimethylindol-2-yl)methylidene]cyclobut-2-en-1-one
• CAS NO: 14238-53-0
• Molecular Formula: C28H29N2O2+
• Molecular Weight: 0
• Mol File: 14238-53-0.mol
• Article Data: 11

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: (4E)-3-hydroxy-2-[(Z)-(1,3,3-trimethylindol-2-ylidene)methyl]-4-[(1,3,3-trimethylindol-2-yl)methylidene]cyclobut-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4E)-3-hydroxy-2-[(Z)-(1,3,3-trimethylindol-2-ylidene)methyl]-4-[(1,3,3-trimethylindol-2-yl)methylidene]cyclobut-2-en-1-one(14238-53-0)
• EPA Substance Registry System: (4E)-3-hydroxy-2-[(Z)-(1,3,3-trimethylindol-2-ylidene)methyl]-4-[(1,3,3-trimethylindol-2-yl)methylidene]cyclobut-2-en-1-one(14238-53-0)

Safety Data

• Hazardous Substances Data: 14238-53-0(Hazardous Substances Data)

Usage

General Description

The chemical compound (4E)-3-hydroxy-2-[(Z)-(1,3,3-trimethylindol-2-ylidene)methyl]-4-[(1,3,3-trimethylindol-2-yl)methylidene]cyclobut-2-en-1-one is a complex organic molecule with a cyclobut-2-en-1-one structure. It contains hydroxy and methylidene groups, along with a trimethylindol-2-ylidene moiety. (4E)-3-hydroxy-2-[(Z)-(1,3,3-trimethylindol-2-ylidene)methyl]-4-[(1,3,3-trimethylindol-2-yl)methylidene]cyclobut-2-en-1-one is a derivative of cyclobut-2-en-1-one with hydroxy and indol-2-ylidene substituents. It is characterized by its double bond configuration and its structural features, which make it a potentially interesting compound for pharmaceutical or chemical applications.

InChI:InChI=1/C28H28N2O2/c1-27(2)19-11-7-9-13-21(19)29(5)23(27)15-17-25(31)18(26(17)32)16-24-28(3,4)20-12-8-10-14-22(20)30(24)6/h7-16H,1-6H3/p+1

Upstream product

• 118-12-7 1,3,3-Trimethyl-2-methyleneindoline 
• 2892-51-5 squaric acid 
• 5418-63-3 1,2,3,3-tetramethyl-3H-indolium iodide 
• 5231-87-8 3,4-diethoxy-3-cyclobuten-1,2-dione 
• 1224096-80-3 Br^(1-)*C₁₄H₁₈NO₂⁽¹⁺⁾ 
• 1640-39-7 2,3,3-trimethylindoleniune 

Relevant articles and documents

A novel fast green method for the preparation of the squaraine dye 3-oxo-4[(1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylene]-2-[(1,3,3-trimethylindolin-2-ylidene)methyl]cyclobut-1-enolate, inner salt

A novel green method was developed for the preparation of a squaraine dye, on an 8-mmol scale, by microwave irradiation of two equivalents of 1,3,3-trimethyl-2-methyleneindoline with one equivalent squaric acid in the green solvent, ethyl l-lactate. The time required for this green synthesis is only 4?min. The target squaraine dye was isolated in excellent yield (81%) and with high purity.

Molecular structure and spectral properties of indolenine based norsquaraines versus squaraines

Novel indolenine based norsquaraine dyes, wherein the oxygen of the squaric acid bridge was substituted with a barbituric or a dicyanomethylene group, were synthesized and their molecular structure, spectral and luminescent properties were compared to those of analogous squaraine dyes. The molecular structure was investigated using X-ray analysis, NMR spectroscopy and ab initio DFT B3LYP/6-311G (d, p) simulations. The calculated populations of possible conformers and the barriers of internal rotations were found to be in good agreement with the experimental data. Norsquaraines absorb and emitt light within the same long-wavelength spectral range as the corresponding squaraines but due to intramolecular H-bonds and increased conformational rigidity they were less sensitive to solvent polarity and the presence of protein (BSA).

Design and Synthesis of Near-Infrared Mechanically Interlocked Molecules for Specific Targeting of Mitochondria

The entrapment of squaraine (SQ) within a molecular container to form rotaxane has been shown to improve the dye stability and the fluorescence proficiency inside the mitochondria. The macrocycle provides shelter and protects the near-infrared (NIR) SQ chromophore from nucleophilic attacks made by the exposed thiol of Cys-containing mitochondrial proteins and mitochondrial glutathione. Herein a microwave-assisted template-directed clipping reaction on low-loading 2-chlorotrityl chloride resin is used to develop an NIR unsymmetrical squaraine rotaxane in high quantum yield.