114747-45-4

Basic information

• Product Name: Technocolor Purple 3
• Synonyms: 1,3,3-Trimethylindolino-6'-(1-piperidinyl)spironaphthoxazine;1,3-Dihydro-1,3,3-trimethyl-6'-(1-piperidinyl)spiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine];Technocolor Purple 3;1,3,3-trimethyl-6'-(piperidin-1-yl)spiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]
• CAS NO: 114747-45-4
• Molecular Formula: C₂₇H₂₉N₃O
• Molecular Weight: 411.54
• Mol File: 114747-45-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 228-230 °C
• Boiling Point: 637.2 °C at 760 mmHg
• Flash Point: 339.2 °C
• Appearance: /
• Density: 1.22
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.99±0.20(Predicted)
• CAS DataBase Reference: Technocolor Purple 3(CAS DataBase Reference)
• NIST Chemistry Reference: Technocolor Purple 3(114747-45-4)
• EPA Substance Registry System: Technocolor Purple 3(114747-45-4)

Safety Data

• Hazardous Substances Data: 114747-45-4(Hazardous Substances Data)

Usage

Uses

1,3,3-Trimethyl-6''-(piperidin-1-yl)spiro[indoline-2,3''-naphtho[2,1-b][1,4]oxazine] is used in preparation of (dihydrotrimethylindol)(piperidinyl)naphthoxazole as light controlled fluorescent modulating material.

Synthetic route

piperidine (110-89-4) + 1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + 1-Nitroso-2-naphthol (131-91-9) → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
Stage #1: 1-Nitroso-2-naphthol With zinc(II) chloride In tetrahydrofuran; water at 20℃; for 0.333333h; Stage #2: piperidine In ethanol for 2h; Michael addition; Reflux; Stage #3: 1,3,3-Trimethyl-2-methyleneindoline With sodium sulfate In ethanol for 20h; Reflux; Inert atmosphere;	68%

1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + 1-Nitroso-4-piperidin-1-yl-naphthalen-2-ol (149140-04-5) → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
In 1,4-dioxane Heating;	30%
In Trichloroethylene for 3.5h; Heating;

piperidine (110-89-4) + 1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + 1-aminonaphthalene-2-ol hydrochloride (1198-27-2) → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
With dimethyl sulfoxide; triethylamine In methanol at 40℃; for 20h;	13%

4-Piperidin-1-yl-1-[(E)-1,3,3-trimethyl-1,3-dihydro-indol-(2Z)-ylidenemethylimino]-1H-naphthalen-2-one → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
With Camphorquinone In toluene Rate constant; also without CQ;

4-Piperidin-1-yl-1-[(E)-1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
In solid matrix Rate constant; Ambient temperature; dark;

4-Piperidin-1-yl-1-[(Z)-1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
In cyclohexane Activation energy; Kinetics; Quantum yield; Further Variations:; Solvents; UV-irradiation;

piperidine (110-89-4) + trityl thiosemicarbazide resin → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: trichloroethene / 0.5 h / Heating 2: trichloroethene / 3.5 h / Heating View Scheme

1,2,3,3-tetramethyl-3H-indolium iodide (5418-63-3) → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / 20 °C 2: trichloroethene / 3.5 h / Heating View Scheme

1-Nitroso-2-naphthol (131-91-9) + ethyl halide → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: trichloroethene / 0.5 h / Heating 2: trichloroethene / 3.5 h / Heating View Scheme

piperidine (110-89-4) + CO → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 55 percent / H2O / Ambient temperature 2: 8 percent / NH2OH*HCl / ethanol / Ambient temperature 3: 30 percent / dioxane / Heating View Scheme
Multi-step reaction with 2 steps 1: methanol / Heating 2: 30 percent / dioxane / Heating View Scheme

[4-(piperidin-1-yl)naphthalene-1,2-dione] (25107-82-8) → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 8 percent / NH2OH*HCl / ethanol / Ambient temperature 2: 30 percent / dioxane / Heating View Scheme

sodium 1,2-naphthoquinone-4-sulfonate (521-24-4) → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 55 percent / H2O / Ambient temperature 2: 8 percent / NH2OH*HCl / ethanol / Ambient temperature 3: 30 percent / dioxane / Heating View Scheme

1-Nitroso-2-naphthol (131-91-9) → 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / Heating 2: 30 percent / dioxane / Heating View Scheme

trimethylsilyl cyanide (7677-24-9) + 6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4) → 1,3,3-Trimethyl-2-{[(E)-4-piperidin-1-yl-2-trimethylsilanyloxy-naphthalen-1-ylimino]-methyl}-2,3-dihydro-1H-indole-2-carbonitrile

Conditions	Yield
In dichloromethane Ambient temperature; Irradiation;	95%

6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4) → 1,3,3-trimethyl-2-[5-(piperidin-1-yl)naphtho[1,2-d]oxazol-2-yl]-3H-indolium bromide

Conditions	Yield
With N-Bromosuccinimide In chloroform for 5h; Heating;	50.3%

6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4) → C27H29N3O

Conditions	Yield
In ethanol at 24.9℃; Rate constant; Equilibrium constant; Thermodynamic data; energy of reaction: ΔH, ΔG, ΔS; energy of activation: ΔH, ΔG, ΔS and Ea;
In toluene at 24.9℃; Rate constant; Equilibrium constant; Thermodynamic data; energy of reaction: ΔH, ΔG, ΔS; energy of activation: ΔH, ΔG, ΔS and Ea;

6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4) → 4-Piperidin-1-yl-1-[(Z)-1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one

Conditions	Yield
In toluene Thermodynamic data; Irradiation; other solvent;
In n-heptane at -87.1℃; Product distribution; Irradiation; various solvents and temperatures, photochromism;

6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4) → 4-Piperidin-1-yl-1-[(Z)-1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one

Conditions	Yield
With methyl 2-naphthyl ketone In toluene at 20.9℃; Quantum yield; Irradiation; also without reagent;
In butan-1-ol Kinetics; Irradiation;

6'-piperidine-1,3,3-trimethylspiro(indoline-2,3'[3H]naphth[2,1-b][1,4]oxazine) (114747-45-4) → zwitterionic or biradicalic photomerocyanine isomer(λmax)

Conditions	Yield
In toluene at 20℃; Irradiation; 450 J; 10 ms; in methanol, methanol-toluene; differentes filtres;

Upstream product

• 118-12-7 1,3,3-Trimethyl-2-methyleneindoline 
• 149140-04-5 1-Nitroso-4-piperidin-1-yl-naphthalen-2-ol 
• 110-89-4 piperidine 
• 131-91-9 1-Nitroso-2-naphthol 
• 521-24-4 sodium 1,2-naphthoquinone-4-sulfonate 
• 25107-82-8 [4-(piperidin-1-yl)naphthalene-1,2-dione] 
• 5418-63-3 1,2,3,3-tetramethyl-3H-indolium iodide 
• 1198-27-2 1-aminonaphthalene-2-ol hydrochloride 

Relevant articles and documents

Photochromism and solvatochromism of push-pull or pull-push spiroindolinenaphthoxazines

The photochromic and solvatochromic behaviour of 17 variously substituted spiroindoline naphthoxazines has been investigated in cyclohexane, toluene, acetonitrile and methanol in fluid solution. Specific parameters such as the wavelengths and the molar ab

One-pot synthesis of photochromic 6′-amino-substituted spirooxazines from 1-nitroso-2-naphthol zinc chelate and indoline base

A series of spirooxazine derivatives containing nitrogen heterocycles were synthesized through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives with the zinc salt of 1-nitroso-2-naphthol using ethanol as solvent. The method is simple, starts from readily accessible and inexpensive reagents, and leads to the synthesis of 6′-substituted spirooxazines in moderate to good yields. We simplified the workup and found that, for some target compounds, recrystallization can effectively improve efficiency of the separation and purification. Georg Thieme Verlag Stuttgart.

One-pot synthesis of 6′-amino-substituted spirooxazines

A one-pot synthesis of 6′-amino-substituted spiroindolinonaphth[2,1- b][1,4]oxazines is developed through the condensation of 2-methylene-1,3,3- trimethylindoline derivatives and 1-amino-2-naphthol in the presence of different secondary amines and oxidizing agents using methanol or toluene as the solvent. The main advantage of the method is its simplicity, and starting from readily accessible reagents, it allows the preparation of amino derivatives of spironaphthoxazine with good yields under mild reaction conditions. Georg Thieme Verlag Stuttgart.