16111-07-2

Basic information

• Product Name: 3',3'-Dimethyl-6-nitro-spiro[2H-1-benzopyran-2,2'-indoline]-1'-ethanol
• Synonyms: 1'-(2-HYDROXYETHYL)-3',3'-DIMETHYL-6-NITROSPIRO[1(2H)-BENZOPYRAN-2,2'-INDOLINE];1-(2-HYDROXYETHYL)-3,3-DIMETHYLINDOLINO-6'-NITROBENZOPYRYLOSPIRAN;3',3'-dimethyl-1'-(beta-hydroxyethyl)-6-nitrospiro[2h-1-benzopyran-2,2'-indoline];3',3'-Dimethyl-6-nitro-spiro[2H-1-benzopyran-2,2'-indoline]-1'-ethanol;2-(3',3'-Dimethyl-6-nitrospiro[chroman-2,2'-indoline]-1'-yl)ethanol;3',3'-Dimethyl-1'-(-hydroxyethyl)-6-nitrospiro2H-1-benzopyran-2,2'-indoline;1-(2HYDROXYETHYL)03,3-DIMETHYLINDOLINO-6''-NITROBENZOPYRYLOSPIRAN;SPIRO[2H-1-BENZOPYRAN-2,2''-[2H]INDOLE]-1''(3''H)-ETHANOL,3'',3''-DIMETHYL-6-NITRO-
• CAS NO: 16111-07-2
• Molecular Formula: C₂₀H₂₀N₂O₄
• Molecular Weight: 352.38
• Product Categories: Spiropyrans (Photochromic);Functional Materials;Photochromic Compounds
• Mol File: 16111-07-2.mol
• Article Data: 37

Chemical Properties

• Melting Point: 164-165°C
• Boiling Point: 540.311 °C at 760 mmHg
• Flash Point: 280.57 °C
• Appearance: /
• Density: 1.36
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 14.46±0.10(Predicted)
• CAS DataBase Reference: 3',3'-Dimethyl-6-nitro-spiro[2H-1-benzopyran-2,2'-indoline]-1'-ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3',3'-Dimethyl-6-nitro-spiro[2H-1-benzopyran-2,2'-indoline]-1'-ethanol(16111-07-2)
• EPA Substance Registry System: 3',3'-Dimethyl-6-nitro-spiro[2H-1-benzopyran-2,2'-indoline]-1'-ethanol(16111-07-2)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 16111-07-2(Hazardous Substances Data)

Usage

Chemical Properties

Dark red solid

Upstream product

• 29636-94-0 1-(2-hydroxyethyl)-2,3,3-trimethyl-3H-indol-1-ium bromide 
• 549507-77-9 protonated merocyanine 
• 97-51-8 5-Nitrosalicylaldehyde 
• 1640-39-7 2,3,3-trimethylindoleniune 
• 540-51-2 2-bromoethanol 
• 93633-69-3 6-[2-[1-(2-Hydroxy-ethyl)-3,3-dimethyl-1,3-dihydro-indol-(2Z)-ylidene]-eth-(Z)-ylidene]-4-nitro-cyclohexa-2,4-dienone 
• 93633-69-3 C₆H₄C(CH₃)2NCH₂CH₂OHCOCHCHC₆H₃NO₂ 
• 27344-29-2 2-(3,3-dimethyl-2-methylene-2,3-dihydro-1H-indol-1-yl)-1-ethanol 
• 36508-00-6 (R/S)-9,9,9a-trimethyl-2,3,9,9a-tetrahydrooxazolo[3,2-a]indole 

Downstream Products

• 93633-69-3 6-[2-[1-(2-Hydroxy-ethyl)-3,3-dimethyl-1,3-dihydro-indol-(2Z)-ylidene]-eth-(Z)-ylidene]-4-nitro-cyclohexa-2,4-dienone 
• 25952-50-5 1-(β-methacryloxyethyl)-3,3-dimethyl-6'-nitrospiro(indoline-2,2'-<2H>benzopyran) 
• 1380212-14-5 1'-{2-[(S)-methacryloyloxypropanoyloxy]ethyl}-3',3'-dimethyl-6-nitrospiro(2H-1-benzopyran-2,2'-indoline) 
• 1380212-17-8 1'-(2-{(S)-2-[(S)-methacryloyloxypropanoyloxy]propanoyloxy}ethyl)-3',3'-dimethyl-6-nitrospiro(2H-1-benzopyran-2,2'-indoline) 

Relevant articles and documents

All-optical integrated logic operations based on chemical communication between molecular switches

Molecular logic gates process physical or chemical "inputs" to generate "outputs" based on a set of logical operators. We report the design and operation of a chemical ensemble in solution that behaves as integrated AND, OR, and XNOR gates with optical in

Optical switching of the Dirac point in graphene multilayer field-effect transistors functionalized with spiropyran

A facile method for achieving optical switching of the Dirac point and conductance in reduced graphene oxide multilayer FETs that are non-covalently functionalized with a photo-responsive spiropyran derivative is presented. The photoresponsive transition from spiropyran to merocyanine induces the reversible optical switching in graphene based FETs.

Light-responsive micelles of spiropyran initiated hyperbranched polyglycerol for smart drug delivery

Light-responsive polymeric micelles have emerged as site-specific and time-controlled systems for advanced drug delivery. Spiropyran (SP), a wellknown photochromic molecule, was used to initiate the ring-opening multibranching polymerization of glycidol to afford a series of hyperbranched polyglycerols (SP-hb-PG). The micelle assembly and disassembly were induced by an external light source owing to the reversible photoisomerization of hydrophobic SP to hydrophilic merocyanine (MC). Transmission electron microscopy, atomic force microscopy, UV/vis spectroscopy, and dynamic light scattering demonstrated the successful assembly and disassembly of SP-hb-PG micelles. In addition, the critical micelle concentration (CMC) was determined through the fluorescence analysis of pyrene to confirm the amphiphilicity of respective SP-hb-PG n(n = 15, 29, and 36) micelles, with CMC values ranging from 13 to 20 mg/L, which is correlated to the length of the polar polyglycerol backbone. Moreover, the superior biocompatibility of the prepared SP-hb-PG was evaluated using WI-38 cells and HeLa cells, suggesting the prospective applicability of the micelles in smart drug delivery systems.

Microwave-assisted crystallization inclusion of spiropyran molecules in indium trimesate films with antidromic reversible photochromism

An indium trimesate metal-organic framework (JUC-120) which possesses a cubic zeolitic MTN topology, as a new analogue to MIL-100(Al, Fe or Cr) compounds, has been successfully synthesized. Its structure exhibits a mesoporous cage (26 A) and high thermal stability. The assembly of nitrobenzospiropyran derivatives (BSP) into JUC-120 nanocrystals (BSP/JUC-120) is achieved by a microwave-assisted crystallization inclusion approach. The BSP/JUC-120 films have been prepared on quartz wafers by a spin-coating method. The successful encapsulation of BSP molecules into the mesopores of the JUC-120 structure has been verified by N2 adsorption and TGA measurements. The photochromic properties of BSP/JUC-120 films are studied by the UV-Vis and fluorescence spectroscopies. More interestingly, metastable open merocyanine (OMC) species are directly generated from the closed spiropyran form (CSP) without photoirradiation and stabilized for a long period in the BSP/JUC-120 film. The open merocyanine isomer bleaches to the closed spiropyran form by ultraviolet or visible light, and the coloration is regained upon standing in the dark, exhibiting antidromic photochromism. Moreover, the BSP/JUC-120 film shows high reversibility and thermal stability of photochromism. This highly efficient MOF film is expected to be promising in the applications of optical devices.

COMPLEXATION OF THE THERMALLY INDUCED COLORED FORM OF 6-NITROSPIROPYRANS IN A POLAR SOLVENT

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Photochromism in cucurbit[8]uril cavity: Inhibition of hydrolysis and modification of the rate of merocyanine-spiropyran transformations

The effect of inclusion complex formation on the photochromic behavior of a spirobenzopyran dye and its merocyanine isomer was studied in aqueous solution using cucurbit[8]uril (CB8) as a host. The merocyanine (MC) and protonated merocyanine (MCH+) were the most stable forms both in water and inside the cavity of CB8. The equilibrium constant of 1:1 complexation with CB8 was found to be 1.7 × 105 and 2.0 × 106 M -1 for the former and latter species, respectively. The encapsulation led to significant change in the rate of the photoinduced and thermal photochromic transformations and hindered the hydrolysis of MC. The effect of CB8 on the reaction kinetics strongly altered with pH. The transition from the spiropyran form to trans-MC in a thermal reaction had 33 kJ mol-1 lower activation energy and more than 5 orders of magnitude smaller Arrhenius pre-exponential factor in CB8 than in water.

Signal processing at the molecular level [26]

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Synthesis of zinc chlorin-spiropyran dyads and their self-aggregation properties

A photochromic spiropyran moiety has been covalently linked to a self-aggregative zinc analog of chlorophyllous pigments. Semi-synthetic zinc chlorins possessing a 31-hydroxy- or 31-methoxy group were used as the chlorophyll model, and the spiropyran part was introduced at the 17-position of the chlorin macrocycle. The spiropyran moiety reversibly isomerized to its opened merocyanine form in the dyads. The photoisomerization induced drastic change in electric dipole moment of the side chain, and photoswitchable chlorophyll aggregation was found in the pigment conjugates.

Application of stimuli-responsive FRET behavior toward cyanide detection in a photo-switchable [2]pseudorotaxane polymer containing the BODIPY donor and the merocyanine acceptor

We have developed a supramolecular (close form) [2]pseudorotaxane polymer containing the green-emissive (λem= 523 nm) BODIPY-based pillar[5]arene host and the non-emissive spiropyran (SP)-based cyano guest (close form), which can be converted t