Product Name

  • Name

    Technocolor Purple 3

  • EINECS
  • CAS No. 114747-45-4
  • Article Data7
  • CAS DataBase
  • Density 1.22 g/cm3;
  • Solubility
  • Melting Point 228-230 °C
  • Formula C27H29N3O
  • Boiling Point 637.2 °C at 760 mmHg
  • Molecular Weight 411.547
  • Flash Point 339.2 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 114747-45-4 (Technocolor Purple 3)
  • Hazard Symbols
  • Synonyms 1,3,3-Trimethylindolino-6'-(1-piperidinyl)spironaphthoxazine;Technocolor Purple 3;
  • PSA 28.07000
  • LogP 5.61430

Synthetic route

piperidine
110-89-4

piperidine

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

1-Nitroso-2-naphthol
131-91-9

1-Nitroso-2-naphthol

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

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

Conditions
ConditionsYield
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%
...Expand
1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

1-Nitroso-4-piperidin-1-yl-naphthalen-2-ol
149140-04-5

1-Nitroso-4-piperidin-1-yl-naphthalen-2-ol

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

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

Conditions
ConditionsYield
In 1,4-dioxane Heating;30%
In Trichloroethylene for 3.5h; Heating;
piperidine
110-89-4

piperidine

1,3,3-Trimethyl-2-methyleneindoline
118-12-7

1,3,3-Trimethyl-2-methyleneindoline

1-aminonaphthalene-2-ol hydrochloride
1198-27-2

1-aminonaphthalene-2-ol hydrochloride

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

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

Conditions
ConditionsYield
With dimethyl sulfoxide; triethylamine In methanol at 40℃; for 20h;13%
...Expand
4-Piperidin-1-yl-1-[(E)-1,3,3-trimethyl-1,3-dihydro-indol-(2Z)-ylidenemethylimino]-1H-naphthalen-2-one

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

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

Conditions
ConditionsYield
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

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

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

Conditions
ConditionsYield
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

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

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

Conditions
ConditionsYield
In cyclohexane Activation energy; Kinetics; Quantum yield; Further Variations:; Solvents; UV-irradiation;
piperidine
110-89-4

piperidine

trityl thiosemicarbazide resin

trityl thiosemicarbazide resin

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

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

Conditions
ConditionsYield
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

1,2,3,3-tetramethyl-3H-indolium iodide

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

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

Conditions
ConditionsYield
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

1-Nitroso-2-naphthol

ethyl halide

ethyl halide

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trichloroethene / 0.5 h / Heating
2: trichloroethene / 3.5 h / Heating
View Scheme
piperidine
110-89-4

piperidine

CO

CO

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

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

Conditions
ConditionsYield
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

[4-(piperidin-1-yl)naphthalene-1,2-dione]

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

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

Conditions
ConditionsYield
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

sodium 1,2-naphthoquinone-4-sulfonate

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

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

Conditions
ConditionsYield
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

1-Nitroso-2-naphthol

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol / Heating
2: 30 percent / dioxane / Heating
View Scheme
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

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

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

1,3,3-Trimethyl-2-{[(E)-4-piperidin-1-yl-2-trimethylsilanyloxy-naphthalen-1-ylimino]-methyl}-2,3-dihydro-1H-indole-2-carbonitrile

1,3,3-Trimethyl-2-{[(E)-4-piperidin-1-yl-2-trimethylsilanyloxy-naphthalen-1-ylimino]-methyl}-2,3-dihydro-1H-indole-2-carbonitrile

Conditions
ConditionsYield
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

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

1,3,3-trimethyl-2-[5-(piperidin-1-yl)naphtho[1,2-d]oxazol-2-yl]-3H-indolium bromide

1,3,3-trimethyl-2-[5-(piperidin-1-yl)naphtho[1,2-d]oxazol-2-yl]-3H-indolium bromide

Conditions
ConditionsYield
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

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

C27H29N3O

C27H29N3O

Conditions
ConditionsYield
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

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

4-Piperidin-1-yl-1-[(Z)-1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one

4-Piperidin-1-yl-1-[(Z)-1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one

Conditions
ConditionsYield
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

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

4-Piperidin-1-yl-1-[(Z)-1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one

4-Piperidin-1-yl-1-[(Z)-1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidenemethylimino]-1H-naphthalen-2-one

Conditions
ConditionsYield
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

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

zwitterionic or biradicalic photomerocyanine isomer(λmax)

zwitterionic or biradicalic photomerocyanine isomer(λmax)

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

1,3,3-Trimethylindolino-6'-(1-piperidinyl)spironaphthoxazine Specification

The 1,3,3-Trimethylindolino-6'-(1-piperidinyl)spironaphthoxazine, with the CAS registry number 114747-45-4, is also known as 1,3-Dihydro-1,3,3-trimethyl-6'-(1-piperidinyl)spiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine] and Technocolor Purple 3. This chemical's molecular formula is C27H29N3O and molecular weight is 411.54. What's more, its IUPAC name is 1',3',3'-Trimethyl-6-piperidin-1-ylspiro[benzo[f][1,4]benzoxazine-3,2'-indole] and systematic name is called 1,3,3-Trimethyl-6'-piperidin-1-yl-1,3-dihydrospiro[indole-2,3'-naphtho[2,1-b][1,4]oxazine]. Classification code of 1,3,3-Trimethylindolino-6'-(1-piperidinyl)spironaphthoxazine is TSCA Flag P [A commenced PMN (Premanufacture Notice) substance].

Physical properties about this chemical are: (1) ACD/LogP: 5.16; (2) # of Rule of 5 Violations: 1; (3) ACD/LogD (pH 5.5): 4.16; (4) ACD/LogD (pH 7.4): 5.11; (5) ACD/BCF (pH 5.5): 493.97; (6) ACD/BCF (pH 7.4): 4380.96; (7) ACD/KOC (pH 5.5): 1537.83; (8) ACD/KOC (pH 7.4): 13638.95; (9) #H bond acceptors: 4; (10) #H bond donors: 0; (11) #Freely Rotating Bonds: 1; (12) Polar Surface Area: 28.07 Å2; (13) Index of Refraction: 1.661; (14) Molar Refractivity: 124.55 cm3; (15) Molar Volume: 336.7 cm3; (16) Surface Tension: 47.1 dyne/cm; (17) Density: 1.22 g/cm3; (18) Flash Point: 339.2 °C; (19) Enthalpy of Vaporization: 94.13 kJ/mol; (20) Boiling Point: 637.2 °C at 760 mmHg; (21) Vapour Pressure: 3.89E-16 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: CC1(C2=CC=CC=C2N(C13C=NC4=C(O3)C=C(C5=CC=CC=C54)N6CCCCC6)C)C
(2) InChI: InChI=1S/C27H29N3O/c1-26(2)21-13-7-8-14-22(21)29(3)27(26)18-28-25-20-12-
6-5-11-19(20)23(17-24(25)31-27)30-15-9-4-10-16-30/h5-8,11-14,17-18H,4,
9-10,15-16H2,1-3H3
(3) InChIKey: YAWJWXXKKHOMQT-UHFFFAOYSA-N

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