13433-31-3

Basic information

• Product Name: 1,3,3-TRIMETHYLINDOLINO-8'-METHOXYBENZOPYRYLOSPIRAN
• Synonyms: 8-METHOXY-1',3',3'-TRIMETHYLSPIRO[1(2H)-BENZOPYRAN-2,2'-INDOLINE];1,3,3-TRIMETHYLINDOLINO-8'-METHOXYBENZOPYRYLOSPIRAN;Trimethylindolinomethoxybenzopyrylospiran;1,3,3-Trimethylindolino-8-methoxybenzopyrylospirane;Photochromiccompound;1,3,3-TRIMETHYLINDOLINO-8-METHOXYBENZOPYRYLOSPIRAN (PHOTOCHROMIC COMPOUND);1,3,3-Trimethyl-8'-methoxyspiro[1H-indole-2(3H),2'-[2H-1]benzopyran];1,3,3-Trimethyl-8'-methoxyspiro[indoline-2,2'-[2H-1]benzopyran]
• CAS NO: 13433-31-3
• Molecular Formula: C20H21NO2
• Molecular Weight: 307.39
• Product Categories: Functional Materials;Photochromic Compounds;Spiropyrans (Photochromic)
• Mol File: 13433-31-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 124 °C
• Boiling Point: 441.3°C at 760 mmHg
• Flash Point: 152.8°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 5.48E-08mmHg at 25°C
• Refractive Index: 1.638
• Solubility: slightly sol. in Ethanol
• PKA: 3.36±0.40(Predicted)
• CAS DataBase Reference: 1,3,3-TRIMETHYLINDOLINO-8'-METHOXYBENZOPYRYLOSPIRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,3-TRIMETHYLINDOLINO-8'-METHOXYBENZOPYRYLOSPIRAN(13433-31-3)
• EPA Substance Registry System: 1,3,3-TRIMETHYLINDOLINO-8'-METHOXYBENZOPYRYLOSPIRAN(13433-31-3)

Safety Data

• Hazardous Substances Data: 13433-31-3(Hazardous Substances Data)

Usage

General Description

1,3,3-Trimethylindolino-8'-methoxybenzopyrylospiran is a type of complex chemical compound, often used in the field of chemistry for various applications. It belongs to the group of compounds known as photochromic materials, which are capable of changing color when exposed to light. This chemical is particularly interesting due to its photochromic attributes. Upon UV light exposure, its structure undergoes a rapid transformation which consequently alters its color. This property gives it potential uses in a range of fields such as smart materials, data storage, optics, and safety equipment. However, details regarding its toxicity, safety handling, and environmental impacts have to be conducted for careful use of this compound.

InChI:InChI=1/C20H21NO2/c1-19(2)15-9-5-6-10-16(15)21(3)20(19)13-12-14-8-7-11-17(22-4)18(14)23-20/h5-13H,1-4H3

Upstream product

• 118-12-7 1,3,3-Trimethyl-2-methyleneindoline 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 64-17-5 ethanol 
• 5418-63-3 1,2,3,3-tetramethyl-3H-indolium iodide 

Relevant articles and documents

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Photochromism of spirobenzopyranindolines and spironaphthopyranindolines

The photocolouration of five spiro[2H-1-benzopyran-2,2′-indoline] compounds (1-5) and two spironaphthopyranindolines (6, 7) to give the ring-opened merocyanine(s) and the subsequent thermal relaxation back to the closed form was studied. A trans-merocyanine but no cis-photoisomer were detected for 1-7 using λexc = 308 nm and a singlet pathway accounts for photocolouration. In contrast to nitrospiropyrans the yield of colouration of spiropyrans is essentially independent of solvent polarity. The relaxation times at 25°C range from 0.01 s for 6 in methylcyclohexane to 17 s for 5 in ethanol, which is due to differences in both activation energies (65-80 kJ mol-1) and the pre-exponential factor (1012-1014 s-1). The photomerocyanine yield is substantially increased upon naphthalene- or acetone-sensitized excitation, where otherwise the same spectral changes, relaxation time and activation parameters were found. Upon excitation of the trans-merocyanine (λexc = 530 nm), a cis-merocyanine with lifetime in the sub ms range could be detected at lower temperatures. Deactivation of the excited trans-merocyanine occurs mainly in the excited singlet state. For 4 and 5, due to an internal heavy-atom effect of bromine substituents, and for 1, a triplet state as a precursor of the cis- and trans-merocyanines could be observed. The effects of structure and medium properties on the photoprocesses are described and the mechanisms of photochromism and thermal decolouration are discussed.

To estimation of pKa for spiropyrans of the indoline series

A mathematically substantiated approach to estimating acid-base characteristics of spiropyrans of the indoline series with account for the ring-chain tautomerism of these compounds was proposed. The pKa values of spiropyrans of various basicity were estimated.