3,3-Diphenyl-3H-naphtho[2,1-b]pyran supplier

Name
3,3-Diphenyl-3H-naphtho[2,1-b]pyran
EINECS
CAS No. 4222-20-2
Article Data37
CAS DataBase
Density 1.187 g/cm³
Solubility
Melting Point 160 °C
Formula C₂₅H₁₈O
Boiling Point 511.1 °C at 760 mmHg
Molecular Weight 334.417
Flash Point 265.1 °C
Transport Information
Appearance Photochromic dye
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
Synonyms 2,2-Diphenyl-5,6-benzo(2H)chromene;3,3-Diphenyl-3H-naphtho[2,1-b]pyran;Variacrol Yellow L;
PSA 9.23000
LogP 6.18920

Synthetic route

: 3923-52-2
1,1-diphenyl-2-propyn-1-ol

: 135-19-3
β-naphthol

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	98%
With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	98%
With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene	98%

: 1210-39-5
3,3-diphenyl-2-propenal

: 135-19-3
β-naphthol

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
With benzoic acid; 3,5-bis-trifluromethylphenylboronic acid In n-heptane at 80℃; for 17h; Sealed tube;	75%

: 530-48-3
1,1-Diphenylethylene

: 708-06-5
2-hydroxynaphthalene-1-carbaldehyde

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid; trimethyl orthoformate In toluene at 20℃; for 6h; Inert atmosphere;	66%
With trifluorormethanesulfonic acid; trimethyl orthoformate In toluene at 20℃; for 6h; Inert atmosphere; regioselective reaction;	66%

: 530-48-3
1,1-Diphenylethylene

: 708-06-5
2-hydroxynaphthalene-1-carbaldehyde

: 149-73-5
trimethyl orthoformate

A: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

B: 2,3-dihydro-1-methoxy-3,3-diphenyl-1H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In toluene at 20℃; for 1h; Inert atmosphere;	A 32% B 33%

...Expand

: 4352-89-0
3H-benzo[f]chromen-3-one

: 16002-63-4
phenylmagnesium iodide

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
With diethyl ether; benzene Erhitzen des nach der Hydrolyse erhaltenen Reaktionsprodukts mit Wasserdampf;

: 209051-94-5
1-(3,3-diphenylprop-2-enylidene)naphthalen-2-one

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
In ethanol at 5℃; under 750.06 Torr; Kinetics; Further Variations:; Pressures; Solvents; Temperatures;
In acetic acid methyl ester at 25℃; under 750.06 Torr; Kinetics; Further Variations:; Pressures; Solvents; Temperatures;
In ethyl acetate at 14℃; Kinetics;
In acetonitrile at 20℃; Kinetics;
In toluene at 24.84℃; Kinetics;

: 209051-94-5
1-(3,3-diphenylprop-2-enylidene)naphthalen-2-one

A: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

B: 194417-56-6
1-[3,3-Diphenyl-prop-2-en-(E)-ylidene]-1H-naphthalen-2-one

Conditions

Conditions	Yield
In acetonitrile at 24℃; Kinetics;

: 194417-56-6
1-[3,3-Diphenyl-prop-2-en-(E)-ylidene]-1H-naphthalen-2-one

A: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

B: 209051-94-5
1-(3,3-diphenylprop-2-enylidene)naphthalen-2-one

Conditions

Conditions	Yield
In acetonitrile at 24℃; Kinetics;

: 119-61-9
benzophenone

(+-)-magnesium chloride-: (+-)-magnesium chloride-

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethylenediamine / tetrahydrofuran / Ambient temperature 2: 62 percent / p-TosOH / CH2Cl2 / Heating View Scheme

: 1-(3,3-diphenylprop-2-enylidene)naphthalen-2-one

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
With polymethylmethacrylate Darkness;
With 1-butyl-3-methylimidazolium camphorsulfonate at 25℃; under 4500450 Torr; Activation energy; Kinetics; Reagent/catalyst; Pressure;

: 119-61-9
benzophenone

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0 - 20 °C 1.2: Cooling with ice 2.1: toluene-4-sulfonic acid / toluene / 2 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 10 °C / Inert atmosphere 1.2: 3 h / Inert atmosphere 2.1: potassium hydroxide / tetrahydrofuran; methanol; hexane / 0 - 20 °C 3.1: pyridinium p-toluenesulfonate; trimethyl orthoformate / 1,2-dichloro-ethane / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -10 °C / Inert atmosphere 1.2: 4 h / 20 °C / Inert atmosphere 1.3: 0.33 h / 0 °C / Inert atmosphere 2.1: 3,5-bis-trifluromethylphenylboronic acid; benzoic acid / n-heptane / 17 h / 80 °C / Sealed tube View Scheme

: 194417-56-6
1-[3,3-Diphenyl-prop-2-en-(E)-ylidene]-1H-naphthalen-2-one

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
In acetonitrile at 20℃; Kinetics;

: 73502-43-9
1,1-diphenyl-3-(trimethylsilyl)prop-2-yn-1-ol

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / tetrahydrofuran; methanol; hexane / 0 - 20 °C 2: pyridinium p-toluenesulfonate; trimethyl orthoformate / 1,2-dichloro-ethane / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate; methanol / tetrahydrofuran 2: montmorillonite K-10 / toluene / 0.75 h / 20 °C View Scheme

: 24892-82-8
1-bromo-2-(1-phenylpropen-1-yl)benzene

: C24H20N2O3S

A: 124421-64-3
2-benzhydrylnaphtho[2,1-b]furan

B: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; 1,4-di(diphenylphosphino)-butane In 2-methyltetrahydrofuran at 100℃; for 48h; Tsuji-Trost Allylation; Schlenk technique; Inert atmosphere; Overall yield = 60 percent; Overall yield = 40 mg; regioselective reaction;

...Expand

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

: 2-bromo-3,3-diphenyl-3H-benzo[f]chromene

Conditions

Conditions	Yield
Stage #1: 3,3-diphenyl-3H-naphtho[2,1-b]pyran With N-Bromosuccinimide In water; dimethyl sulfoxide at 20℃; for 0.333333h; Stage #2: With toluene-4-sulfonic acid In toluene for 2.5h; Reflux;	85%

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

: 2-benzhydryl-naphtho[2,1-b]furan

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 19.85℃; for 12h; Irradiation;	66%

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

: 119-61-9
benzophenone

Conditions

Conditions	Yield
In acetonitrile at 13℃; Product distribution; Irradiation; photodecomposition and singlet oxygen production during photosensitization;

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

: 209051-94-5
1-(3,3-diphenylprop-2-enylidene)naphthalen-2-one

Conditions

Conditions	Yield
In toluene at 25℃; Quantum yield; Rate constant; Irradiation; flash photolysis (ca 60 J, ca 50 μs); spectrokinetic properties;
In toluene at 25℃; Kinetics; ring opening; Flash photolysis;
In (2)H8-toluene at -73.16℃; Solvent; Temperature; UV-irradiation;

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

A: 209051-94-5
1-(3,3-diphenylprop-2-enylidene)naphthalen-2-one

B: 194417-56-6
1-[3,3-Diphenyl-prop-2-en-(E)-ylidene]-1H-naphthalen-2-one

Conditions

Conditions	Yield
In acetonitrile Product distribution; Rate constant; Irradiation; bleaching at the photostationary state in MeCN solution; photochromic equilibrium; kinetic and structural studies of the photochromic process of 3H-naphthopyrans by UV and NMR spectroscopy;
In ethyl acetate at 14℃; Kinetics; UV-irradiation;
In acetonitrile at 24℃; Irradiation; Title compound not separated from byproducts.;

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

: 1-(3,3-diphenylprop-2-enylidene)naphthalen-2-one

Conditions

Conditions	Yield
In acetonitrile UV-irradiation;
In acetonitrile at 20℃; UV-irradiation;
With polymethylmethacrylate UV-irradiation;

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

: C25H18O

Conditions

Conditions	Yield
Stage #1: 3,3-diphenyl-3H-naphtho[2,1-b]pyran at -193.16℃; UV-irradiation; neat (no solvent, solid phase); Stage #2: at -193.16℃; visible light;

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

: 3,3-diphenyl-2-(pyren-1-yl)-3H-benzo[f]chromene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / water; dimethyl sulfoxide / 0.33 h / 20 °C 1.2: 2.5 h / Reflux 2.1: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / water; tetrahydrofuran / 15 h / Inert atmosphere; Reflux View Scheme

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

: C41H26O

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / water; dimethyl sulfoxide / 0.33 h / 20 °C 1.2: 2.5 h / Reflux 2.1: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / water; tetrahydrofuran / 15 h / Inert atmosphere; Reflux 3.1: benzene / 24.84 °C / Irradiation View Scheme

: 4222-20-2
3,3-diphenyl-3H-naphtho[2,1-b]pyran

: 194417-56-6
1-[3,3-Diphenyl-prop-2-en-(E)-ylidene]-1H-naphthalen-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (2)H8-toluene / -73.16 °C / UV-irradiation 2: toluene / 24.84 °C / UV-irradiation View Scheme

3,3-Diphenyl-3H-naphtho[2,1-b]pyran Specification

The CAS register number of 3,3-Diphenyl-3H-naphtho[2,1-b]pyran is 4222-20-2. It also can be called as 3H-Naphtho[2,1-b]pyran,3,3-diphenyl- and the IUPAC name about this chemical is 3,3-diphenylbenzo[f]chromene. The molecular formula about this chemical is C₂₅H₁₈O and the molecular weight is 334.41. It belongs to the following product categories, such as Azobenzene, etc. (Photochromic Compounds); Functional Materials; Photochromic Compounds and so on.

Physical properties about 3,3-Diphenyl-3H-naphtho[2,1-b]pyran are: (1)ACD/LogP: 6.89; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.89; (4)ACD/LogD (pH 7.4): 6.89; (5)ACD/BCF (pH 5.5): 102044.59; (6)ACD/BCF (pH 7.4): 102044.59; (7)ACD/KOC (pH 5.5): 133927.77; (8)ACD/KOC (pH 7.4): 133927.77; (9)#H bond acceptors: 1; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 9.23Å²; (12)Index of Refraction: 1.679; (13)Molar Refractivity: 106.27 cm³; (14)Molar Volume: 281.5 cm³; (15)Polarizability: 42.12x10^-24cm³; (16)Surface Tension: 54.3 dyne/cm; (17)Enthalpy of Vaporization: 75.25 kJ/mol; (18)Boiling Point: 511.1 °C at 760 mmHg; (19)Vapour Pressure: 4.67E-10 mmHg at 25°C.

Preparation: this chemical can be prepared by 1,1-diphenyl-prop-2-yn-1-ol and naphthalen-2-ol. This reaction will need reagent TsOH and solvent toluene. The reaction time is 2 hour(s) at heating. The yield is about 62%.

Uses of 3,3-Diphenyl-3H-naphtho[2,1-b]pyran: it can be used to produce 2-benzhydrylidene-1,2-dihydro-naphtho[2,1-b]furan at temperature of 19.85 ℃. This reaction will need reagent dimethylformamide with reaction time of 12 hours. The yield is about 66%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O2c1ccc5c(c1\C=C/C2(c3ccccc3)c4ccccc4)cccc5
(2)InChI: InChI=1/C25H18O/c1-3-10-20(11-4-1)25(21-12-5-2-6-13-21)18-17-23-22-14-8-7-9-19(22)15-16-24(23)26-25/h1-18H
(3)InChIKey: UBNNJVRNPJVYBU-UHFFFAOYAA
(4)Std. InChI: InChI=1S/C25H18O/c1-3-10-20(11-4-1)25(21-12-5-2-6-13-21)18-17-23-22-14-8-7-9-19(22)15-16-24(23)26-25/h1-18H
(5)Std. InChIKey: UBNNJVRNPJVYBU-UHFFFAOYSA-N

Product Name

3,3-Diphenyl-3H-naphtho[2,1-b]pyran

Synthetic route

3,3-Diphenyl-3H-naphtho[2,1-b]pyran Specification

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