1-Ethenyl pyrene supplier | CasNO.17088-21-0

Name
1-vinylpyrene
EINECS
CAS No. 17088-21-0
Article Data15
CAS DataBase
Density 1.214g/cm³
Solubility
Melting Point 87-89 °C
Formula C18H12
Boiling Point 409.8°Cat760mmHg
Molecular Weight 228.293
Flash Point 193°C
Transport Information
Appearance
Safety Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Pyrene,3-vinyl- (8CI); 1-Ethenylpyrene; 1-Vinylpyrene; 3-Vinylpyrene
PSA 0.00000
LogP 5.22700

Synthetic route

: 61078-14-6
1-methyl-2-(methylsulfonyl)-1H-benzo[d]imidazole

: 3029-19-4
pyrene-1-aldehyde

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	95%

: 3029-19-4
pyrene-1-aldehyde

: 1779-49-3
Methyltriphenylphosphonium bromide

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: pyrene-1-aldehyde In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	82%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Wittig Olefination; Inert atmosphere; Stage #2: pyrene-1-aldehyde In tetrahydrofuran at 20℃; for 12h; Wittig Olefination; Inert atmosphere;	70%
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; Stage #2: pyrene-1-aldehyde In tetrahydrofuran; hexane at 20℃; Wittig reaction; Further stages.;	62%
With n-butyllithium In tetrahydrofuran; hexane for 12h; Ambient temperature;	40%

: 3029-19-4
pyrene-1-aldehyde

: 2065-66-9
methyl-triphenylphosphonium iodide

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
Stage #1: methyl-triphenylphosphonium iodide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: pyrene-1-aldehyde In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;	70%
Stage #1: methyl-triphenylphosphonium iodide With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Wittig reaction; Inert atmosphere; Stage #2: pyrene-1-aldehyde In tetrahydrofuran at 20℃; for 12h; Wittig reaction; Inert atmosphere;	59%
With lithium diisopropyl amide 1) THF, -78 deg C to RT, 16h, 2) THF, RT, 6h; Yield given. Multistep reaction;

: 18424-76-5
dimethyl malonate sodium salt

: 1-(1-pyrenyl)ethyl carbonate

A: 17088-21-0
1-vinylpyrene

B: 2-(1-Pyren-1-yl-ethyl)-malonic acid dimethyl ester

Conditions

Conditions	Yield
With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 80℃; for 48h;	A n/a B 5%
With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 80℃; for 48h;

...Expand

: 65954-42-9
alpha-Methyl-1-pyrenemethanol

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
With 1,4-dioxane; aluminum oxide at 340 - 360℃; under 6 Torr;

: 139225-56-2
cis-1,2-Di(1-pyrenyl)cyclobutane

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
In acetonitrile at 23.9℃; Quantum yield; Mechanism; Irradiation; other solvent benzene, effect of added N,N-dimethyl-p-toluidine, 1,4-dicyanobenzene, benzophenone;

: 139225-55-1, 139225-56-2, 139343-98-9, 139343-99-0, 139891-96-6, 139891-97-7
trans-1,2-Di(1-pyrenyl)cyclobutane

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
In acetonitrile at 23.9℃; Quantum yield; Mechanism; Irradiation; other solvent benzene, effect of added N,N-dimethyl-p-toluidine, 1,4-dicyanobenzene, benzophenone;

: 91-22-5
quinoline

: 71-43-2
benzene

vaporous 3--acrylic acid: vaporous 3--acrylic acid

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
With copper borate aluminium oxide at 520 - 580℃; under 10 - 20 Torr;

...Expand

: 123-91-1
1,4-dioxane

: 65954-42-9
alpha-Methyl-1-pyrenemethanol

aluminium oxide: aluminium oxide

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
at 340 - 360℃; under 6 Torr;

...Expand

: 3264-21-9
1-acetylpyrene

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: copper oxide-chromium oxide; methanol / 80 °C / 13239.1 Torr / Hydrogenation 2: dioxane; aluminium oxide / 340 - 360 °C / 6 Torr View Scheme

: 1386958-88-8
phenyl(pyren-1-ylmethyl)selane

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
With dihydrogen peroxide In methanol; water

: 2595-90-6
1-bromomethylpyrene

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / methanol / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: dihydrogen peroxide / methanol; water View Scheme

: 74-85-1
ethene

: C53H76Cl2P2Ru

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.05h;

: 129-00-0
pyrene

: 17088-21-0
1-vinylpyrene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: titanium tetrachloride / dichloromethane / 2.5 h / 0 - 20 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2.2: 4 h / 0 - 20 °C / Inert atmosphere View Scheme

: 17088-21-0
1-vinylpyrene

: 3264-21-9
1-acetylpyrene

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; C21H19N5Pd(2+)*2BF4(1-) In decane; acetonitrile at 45℃; for 12h; Wacker Oxidation;	95%

: Grubbs catalyst first generation

: 17088-21-0
1-vinylpyrene

: C53H76Cl2P2Ru

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h;	84%

: 17088-21-0
1-vinylpyrene

: 1407790-22-0
6-iodo-9-octyl-9H-carbazole-3-carbaldehyde

: (E)-9-octyl-6-(2-(pyren-1-yl)vinyl)-9H-carbazole-3-carbaldehyde

Conditions

Conditions	Yield
With palladium diacetate; triethylamine In acetonitrile at 90℃; for 24h; Heck Reaction; Inert atmosphere;	79%

: 106-37-6
1.4-dibromobenzene

: 17088-21-0
1-vinylpyrene

: 137455-36-8
1,4-bis[(E)-2-(pyren-1-yl)vinyl]benzene

Conditions

Conditions	Yield
Stage #1: 1.4-dibromobenzene With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h; Heck reaction; Inert atmosphere; Stage #2: 1-vinylpyrene In N,N-dimethyl-formamide at 90℃; for 12h; Heck reaction; Inert atmosphere;	76%

: 608-72-0
2,4,6-tribromomesitylene

: 17088-21-0
1-vinylpyrene

: 1330196-44-5
(E)-1-(2,4,6-trimethyl-3,5-bis[(E)-2-(pyren-1-yl)vinyl]styryl)pyrene

Conditions

Conditions	Yield
Stage #1: 2,4,6-tribromomesitylene With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h; Heck reaction; Inert atmosphere; Stage #2: 1-vinylpyrene In N,N-dimethyl-formamide at 90℃; for 12h; Heck reaction; Inert atmosphere;	75%

: 626-39-1
1,3,5-trisbromobenzene

: 17088-21-0
1-vinylpyrene

: 779357-39-0
1,3,5-tris[(E)-2-(pyren-1-yl)vinyl]benzene

Conditions

Conditions	Yield
Stage #1: 1,3,5-trisbromobenzene With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h; Heck reaction; Inert atmosphere; Stage #2: 1-vinylpyrene In N,N-dimethyl-formamide at 90℃; for 12h; Heck reaction; Inert atmosphere;	73%

: 17088-21-0
1-vinylpyrene

: (3-methylpyridin-2-yl)diphenylphosphine oxide

: (E)-(3-methylpyridin-2-yl)(phenyl)(2-(2-(pyridin-1-yl)vinyl)phenyl)phosphine oxide

Conditions

Conditions	Yield
With (S)-acetamidoalanine; silver(I) acetate; palladium diacetate at 70℃; for 48h;	72%

: 87-82-1
hexabromobenzene

: 17088-21-0
1-vinylpyrene

: 1330196-45-6
1,2,3,4,5,6-hexakis[(E)-2-(pyren-1-yl)vinyl]benzene

Conditions

Conditions	Yield
Stage #1: hexabromobenzene With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h; Heck reaction; Inert atmosphere; Stage #2: 1-vinylpyrene In N,N-dimethyl-formamide at 90℃; for 36h; Heck reaction; Inert atmosphere;	69%

: 17088-21-0
1-vinylpyrene

: 93654-96-7
2-(pyren-1-yl)ethan-1-ol

Conditions

Conditions	Yield
Stage #1: 1-vinylpyrene With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 50℃; for 1h; Inert atmosphere; Stage #2: With sodium perborate; water In tetrahydrofuran at 20℃; Inert atmosphere;	66%

: 17088-21-0
1-vinylpyrene

: 925674-50-6
4-bromo-4′-(N,N′-diphenylamine)stilbene

: N,N-diphenyl-4-((E)-4-((E)-2-(pyren-2-yl)vinyl)styryl)aniline

Conditions

Conditions	Yield
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h; Heck Reaction; Inert atmosphere;	65%

: 17088-21-0
1-vinylpyrene

: 4-((E)-2-(6-((E)-4-bromostyryl)-9-octyl-9H-carbazol-2-yl)vinyl)-N,N-diphenylaniline

: 4-((E)-2-(9-Octyl-6-((E)-4-((E)-2-(pyren-2-yl)vinyl)styryl)-9H-carbazol-2-yl)vinyl)-N,N-diphenylaniline

Conditions

Conditions	Yield
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h; Heck Reaction; Inert atmosphere;	62%

: 17088-21-0
1-vinylpyrene

: 197969-58-7
2,7-dibromo-9,9-diethyl-9H-fluorene

: (E,E)-2,7-bis(1'-pyrenylvinylene)-9,9-diethylfluorene

Conditions

Conditions	Yield
With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide at 90℃; for 48h; Heck coupling;	55%

: 17088-21-0
1-vinylpyrene

: 4-((E)-2-(6-((E)-2-(6-((E)-4-bromostyryl)-9-octyl-9H-carbazol-3-yl)vinyl)-9-octyl-9H-carbazol-2-yl)vinyl)-N,N-diphenylaniline

: 4-((E)-2-(9-octyl-6-((E)-2-(9-octyl-6-((E)-4-((E)-2-(pyren-2-yl)-vinyl)styryl)-9H-carbazol-3-yl)vinyl)-9H-carbazol-2-yl)vinyl)-N,N-diphenylaniline

Conditions

Conditions	Yield
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h; Heck Reaction; Inert atmosphere;	54%

: 17088-21-0
1-vinylpyrene

: 1122-91-4
4-bromo-benzaldehyde

: (E)-4-(2-(pyren-1-yl)vinyl)benzaldehyde

Conditions

Conditions	Yield
With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide at 85℃; for 48h; Heck coupling;	50%

: 7321-55-3
2,2-dimethylmalononitrile

: 17088-21-0
1-vinylpyrene

: 73183-34-3
bis(pinacol)diborane

: 2-(pyren-1-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanenitrile

Conditions

Conditions	Yield
Stage #1: bis(pinacol)diborane With (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(dicyclohexylphosphane); copper acetylacetonate; cesium fluoride; lithium tert-butoxide In dibutyl ether at 20℃; for 0.5h; Inert atmosphere; Sealed tube; Stage #2: 2,2-dimethylmalononitrile; 1-vinylpyrene In dibutyl ether at 100℃; for 14h; Inert atmosphere; Sealed tube; regioselective reaction;	40%

...Expand

: 474687-62-2
2-bromo-bispiro(9,10-dihydroanthracene-9,7′-7′H-fluorene-10,7″-7″H-fluorene)

: 17088-21-0
1-vinylpyrene

: C56H34

Conditions

Conditions	Yield
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In DMF (N,N-dimethyl-formamide) for 15h; Heck Reaction; Heating / reflux;	32%

: 17088-21-0
1-vinylpyrene

: 2039-80-7
N,N-dimethy-4-vinylaniline

: 102769-24-4, 102769-25-5
cis-1-(4-dimethylaminophenyl)-2-pyren-1-ylcyclobutane

: 102769-24-4, 102769-25-5
trans-1-(4-dimethylaminophenyl)-2-pyren-1-ylcyclobutane

Conditions

Conditions	Yield
In benzene at 23.9℃; for 3h; Product distribution; Irradiation; various solvents, various yield of products;
In benzene for 3h; Irradiation;

...Expand

: 17088-21-0
1-vinylpyrene

: 3029-19-4
pyrene-1-aldehyde

Conditions

Conditions	Yield
In methanol for 0.0333333h; Quantum yield; Mechanism; Irradiation; in different solvents;

: 17088-21-0
1-vinylpyrene

: 17088-22-1
1-ethylpyrene

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In tetrahydrofuran

: 17088-21-0
1-vinylpyrene

A: 139225-56-2
cis-1,2-Di(1-pyrenyl)cyclobutane

: 139225-55-1, 139225-56-2, 139343-98-9, 139343-99-0, 139891-96-6, 139891-97-7
trans-1,2-Di(1-pyrenyl)cyclobutane

Conditions

Conditions	Yield
In acetonitrile for 3h; Ambient temperature; Irradiation;

1-Ethenyl pyrene Chemical Properties

Molecular Structure of 1-Ethenyl pyrene (CAS NO.17088-21-0):

IUPAC: 1-Vinylpyrene
Molecular Formula:C₁₈H₁₂
Molecular Weight:228.2879
Density:1.214 g/cm³
Flash Point:193^oC
Boiling Point:409.8^oC at 760 mmHg
SMILES:c4cc2ccc1ccc(\C=C)c3c1c2c(cc3)c4
InChI:InChI=1/C18H12/c1-2-12-6-7-15-9-8-13-4-3-5-14-10-11-16(12)18(15)17(13)14/h2-11H,1H2
InChIKey:WPMHMYHJGDAHKX-UHFFFAOYAE
Index of Refraction:1.842
Molar Volume:187.9 cm³
Surface Tension:56.2 dyne/cm
Molar Refractivity:83.38 cm³
Enthalpy of Vaporization:63.63 kJ/mol
Vapour Pressure:1.5E-06 mmHg at 25^oC

1-Ethenyl pyrene Toxicity Data With Reference

1.		mma-sat 10 nmol/plate		CNREA8 Cancer Research. 40 (1980),642.
2.		skn-mus TDLo:3651 µg/kg:ETA		CNREA8 Cancer Research. 40 (1980),642.

1-Ethenyl pyrene Safety Profile

Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

1-Ethenyl pyrene Specification

1-Ethenyl pyrene with cas registry number of 17088-21-0 is also known as 1-Vinylpyrene ; 1-Ethenylpyrene ; 3-Vinylpyrene ; Pyrene,1-ethenyl-(9CI) ; Pyrene,3-vinyl- . 1-Ethenyl pyrene can be prepared in a single reaction stage by reacting the corresponding Acetylpyrene with a metal alkoxide in an inert organic solvent, e.g. Xylene, at a temperature above 110^oC. which, for some reaction conditions, optimally is between 130^oC and 150^oC. The presence of hydroquinone in the mixture reduces the time and increases the yield of the reaction. 1-Ethenyl pyrene with cas registry number of 17088-21-0 is used as an intermediate in synthesis of Nizatidine .

Product Name

1-vinylpyrene

Synthetic route

1-Ethenyl pyrene Chemical Properties

1-Ethenyl pyrene Toxicity Data With Reference

1-Ethenyl pyrene Safety Profile

1-Ethenyl pyrene Specification

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