Pentacene supplier | CasNO.135-48-8

Name
Pentacene
EINECS 205-193-7
CAS No. 135-48-8
Article Data40
CAS DataBase
Density 1.232 g/cm³
Solubility Insoluble in water
Melting Point >300 °C(lit.)
Formula C₂₂H₁₄
Boiling Point 524.67 °C at 760 mmHg
Molecular Weight 278.353
Flash Point 264.522 °C
Transport Information
Appearance solid
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,3:6,7-Dibenzanthracene;Benzo[b]naphthacene;Dibenz[b,i]anthracene;NSC 90784;lin-Dibenzanthracene;lin-Naphthoanthracene;
PSA 0.00000
LogP 6.29940

Synthetic route

: 783321-43-7
6,13-dihydro-6,13-epithiomethanopentacen-16-one

: 135-48-8
pentacene

Conditions

Conditions	Yield
at 220℃; UV-irradiation;	100%

: 6,13-dihydro-6,13-ethanopentacene-15,16-dione

: 135-48-8
pentacene

Conditions

Conditions	Yield
In chloroform at 20℃; Irradiation;	96%
In toluene at 20℃; Irradiation;	74%
In toluene UV-irradiation;
Neat (no solvent); Irradiation using laser light;
for 0.0833333h; Neat (no solvent); Irradiation using xenon lamp;

: 6,13-dihydro-6,13-dihydroxypentacene

: 135-48-8
pentacene

Conditions

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In water; N,N-dimethyl-formamide at 0℃; for 0.0291667h; Darkness;	93%
With hydrogenchloride In tetrahydrofuran at -50℃; for 0.25h; Inert atmosphere; Reflux;

: 20244-36-4
5,14-dihydro-pentacene

: 135-48-8
pentacene

Conditions

Conditions	Yield
palladium on activated charcoal In xylene for 72h; Heating;	92%

: 2,2'-(1,3-phenylenebis(methylene))dibenzaldehyde

: 135-48-8
pentacene

Conditions

Conditions	Yield
With trifluoroacetic acid at 20℃; for 5h;	83%

: 3029-32-1
6,13-pentacenequinone

: 135-48-8
pentacene

Conditions

Conditions	Yield
Stage #1: 6,13-pentacenequinone With sodium tetrahydroborate; water In tetrahydrofuran at 0 - 60℃; for 2h; Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In N,N-dimethyl-formamide at 0℃; for 0.0208333h; Darkness;	79%
Multistep reaction.;	54%
With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Inert atmosphere; Cooling with ice;	54%
With oxidizing agent; diborane 1.) diglyme; Multistep reaction;
Multi-step reaction with 2 steps 1: 70 percent / KBH4 / methanol / several d 2: 67 percent / KI, sodium hyposulfite / acetic acid / 3 h / Heating View Scheme

: 76727-08-7
dihydroxy-6,13 dihydro-6,13 pentacene cis

: 135-48-8
pentacene

Conditions

Conditions	Yield
With sodium thiosulfate; potassium iodide In acetic acid for 3h; Heating;	67%

: 104942-18-9
6,13-dihydro-14-hydroxy-6,13-ethenopentacene

: 135-48-8
pentacene

Conditions

Conditions	Yield
With 1,2,4,5-tetrazine-3,6-dicarboxylic acid dimethyl ester In dipentyl ether for 0.025h; Reflux;	48%

: 1671-87-0
3,6-di(2'-pyridyl)-1,2,4,5-tetrazine

: 104942-18-9
6,13-dihydro-14-hydroxy-6,13-ethenopentacene

A: 135-48-8
pentacene

B: 1370025-49-2
6,13-dihydro-6,13-[4',5']-3',6'-(di-2"-pyridyl)pyridazinopentacene

C: 36901-11-8
3,6-di(pyridin-2'-yl)-s-tetrazine

D: 1671-86-9
3,6-di(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine

Conditions

Conditions	Yield
In dipentyl ether for 2h; Diels-Alder-retro-Diels-Alder; Reflux;	A 28% B n/a C n/a D n/a

...Expand

: 286-85-1
1H-cyclopropa[b]naphthalene

A: 13579-08-3
6,13-dihydropentacene

B: 21969-45-9
1,2-bis(2-naphthyl)ethane

C: 135-48-8
pentacene

D: 112223-66-2
6,7-dihydropentaphene

E: 91-57-6
2-Methylnaphthalene

Conditions

Conditions	Yield
With potassium sand; cadmium(II) chloride In tetrahydrofuran at -40 - 0℃; Product distribution; Mechanism; multistep reaction; further temperatures, further metal surface;	A 2% B 2% C 2% D 4% E 24%

...Expand

: 904913-36-6
6,13-dihydro-6,13-methanopentacene-15-one

: 135-48-8
pentacene

Conditions

Conditions	Yield
In tetrahydrofuran Photolysis;	16.2%
at 150 - 160℃; for 1h;
at -268.16℃; for 0.25h; UV-irradiation;

: 1037314-15-0
5,14-dihydro-5,14-methanopentacen-15-one

: 135-48-8
pentacene

Conditions

Conditions	Yield
In tetrahydrofuran Temperature; Wavelength; Photolysis;	16.2%
In tetrahydrofuran UV-irradiation;

: 13579-08-3
6,13-dihydropentacene

: 135-48-8
pentacene

Conditions

Conditions	Yield
With nitrobenzene; 9,10-phenanthrenequinone
With chloranil; xylene
With copper at 380℃; under 12 - 20 Torr;

: Δ4a(14a),7a(11a)-octadecahydro-pentacene

: 135-48-8
pentacene

Conditions

Conditions	Yield
With palladium on activated charcoal at 245℃;

: 56-23-5
tetrachloromethane

: 13579-08-3
6,13-dihydropentacene

: 118-75-2
chloranil

: 135-48-8
pentacene

...Expand

: 859943-68-3
15r.16c.18.19-tetrachloro-17.20-dioxo-6.13.15.16.17.20-hexahydro-6.13-o-benzeno-pentacene

: 98-95-3
nitrobenzene

A: 135-48-8
pentacene

B: 118-75-2
chloranil

...Expand

: 13579-08-3
6,13-dihydropentacene

: 98-95-3
nitrobenzene

: 84-11-7
9,10-phenanthrenequinone

: 135-48-8
pentacene

...Expand

: 100790-90-7, 100895-73-6
5,14:7,12-diepoxy-5,7,12,14-tetrahydro-5,7,12,14-tetrakis(trimethylsilyl)pentacene

: 135-48-8
pentacene

Conditions

Conditions	Yield
With lithium aluminium tetrahydride; trifluoroacetic acid 1.) benzene, 3 h, 2.) THF, RT, 2 h; Multistep reaction;

: 286-85-1
1H-cyclopropa[b]naphthalene

A: 13579-08-3
6,13-dihydropentacene

B: 21969-45-9
1,2-bis(2-naphthyl)ethane

C: 135-48-8
pentacene

D: 112223-66-2
6,7-dihydropentaphene

Conditions

Conditions	Yield
With potassium mirror; cadmium(II) chloride 1.) THF, 0 deg C, 30 min; r.t., 45 min, 2.) THF, reflux, overnight; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
With potassium mirror; cadmium(II) chloride 1.) THF, 0 deg C, 30 min; r.t., 45 min, 2.) THF, reflux, overnight; Multistep reaction. Further byproducts given. Yields of byproduct given;
With potassium sand; cadmium(II) chloride 1.) THF, -40 deg C, 50 min, 2.) THF, r.t., overnight; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 57878-28-1
1,5-dibenzoyl-2,4-dimethyl-benzene

A: 13579-08-3
6,13-dihydropentacene

B: 135-48-8
pentacene

C: 613-12-7
2-methylanthracene

D hydrocarbon C22H16: hydrocarbon C22H16

Conditions

Conditions	Yield
Pyrolysis;

...Expand

: 860563-90-2
5-benzyl-2,4-dimethyl-benzophenone

copper-powder: copper-powder

A: 135-48-8
pentacene

B: 222-93-5
pentaphene

Conditions

Conditions	Yield
Erhitzen des Reaktionsprodukts mit Chloranil in Xylol;

...Expand

: C24H17NO2S

: 135-48-8
pentacene

Conditions

Conditions	Yield
retro Diels-Alder reaction; Heating;

: 504423-06-7
7,14-dihydropentacene-5,12-dione

: 504423-07-8
pentacene-5,7(12H,14H)-dione

: 111-96-6
diethylene glycol dimethyl ether

: 135-48-8
pentacene

Conditions

Conditions	Yield
With hydrogenchloride; sodium borohydrid; acetic acid In methanol; water

...Expand

: 23912-79-0
pentacene-5,7,12,14-tetraone

: 2269-22-9
aluminum tri-sec-butoxide

: 135-48-8
pentacene

Conditions

Conditions	Yield
In cyclohexanol

: 942262-46-6
6,13-dihydro-6,13-methano-15-tert-butoxypentacene

: 135-48-8
pentacene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 83 percent / sulfuric acid; H2O / tetrahydrofuran / 48 h / 20 °C 2: 60 percent / triethylamine; sulfur trioxide/pyridine / CH2Cl2; dimethylsulfoxide / 12.5 h / 20 °C 3: 1 h / 150 - 160 °C View Scheme

: 942262-51-3
6,13-dihydro-6,13-methano-15-hydroxypentacene

: 135-48-8
pentacene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / triethylamine; sulfur trioxide/pyridine / CH2Cl2; dimethylsulfoxide / 12.5 h / 20 °C 2: 1 h / 150 - 160 °C View Scheme

: 6,13-dihydro-6,13-ethenopentacene

: 135-48-8
pentacene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / N-methylmorpholine-N-oxide*2H2O; OsO4 / 2-methyl-propan-2-ol; acetone / 32 h / 20 °C 2: 43 percent / trifluoroacetic anhydride; DMSO / CH2Cl2 / -60 - 20 °C 3: toluene / UV-irradiation View Scheme

: 6,13-dihydro-15,17-dihydroxy-6,13-ethanopentacene

: 135-48-8
pentacene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 43 percent / trifluoroacetic anhydride; DMSO / CH2Cl2 / -60 - 20 °C 2: toluene / UV-irradiation View Scheme

: 118-92-3
anthranilic acid

1-chloro-4-methyl-thioxanthone: 1-chloro-4-methyl-thioxanthone

: 135-48-8
pentacene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: isoamyl nitrite / tetrahydrofuran / 2 h / Heating 1.2: 71 percent / DDQ / CHCl3 / 2 h / 20 °C 2.1: 98 percent / N-methylmorpholine-N-oxide*2H2O; OsO4 / 2-methyl-propan-2-ol; acetone / 32 h / 20 °C 3.1: 43 percent / trifluoroacetic anhydride; DMSO / CH2Cl2 / -60 - 20 °C 4.1: toluene / UV-irradiation View Scheme

: 135-48-8
pentacene

: N-(2'-methyl-4-nitrophenyl)maleimide

: C33H22N2O4

Conditions

Conditions	Yield
In toluene at 100℃; Diels-Alder Cycloaddition; Sealed tube;	100%

: 135-48-8
pentacene

: 122-57-6
1-Phenylbut-1-en-3-one

: C32H24O

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	99%

: 135-48-8
pentacene

: 94-41-7
benzalacetophenone

: C37H26O

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	99%

: 135-48-8
pentacene

: 587055-89-8
N-[(1S,2R)-1-methyl-2-phenyl-2-hydroxyethyl]maleimide

: N-[(1S,2R)-1-methyl-2-phenyl-2-hydroxyethyl]-4,11[2',3']naphtho-3a,4,11,11a-tetrahydro-1H-naphtho[2,3-f]isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
In xylene at 130℃; for 48h; Diels-Alder addition;	98%

: 135-48-8
pentacene

: 105507-76-4
C11H9FO3

: C33H23FO3

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	96%

: 135-48-8
pentacene

: 42393-11-3, 97897-42-2
Methyl-p-chlorbenzylidenpyruvat

: C33H23ClO3

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	95%

: 135-48-8
pentacene

: 42393-13-5
Methyl-3,4-dichlorbenzylidenpyruvat

: C33H22Cl2O3

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	94%

: 104093-34-7
4-(4-bromophenyl)-2-oxo-3-butenoic acid methyl ester

: 135-48-8
pentacene

: C33H23BrO3

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	93%

: 135-48-8
pentacene

: 7258-98-2
epidioxy-6,13 dihydro-6,13 pentacene

Conditions

Conditions	Yield
With potassium dichromate; hematoporphyrin chlorohydrate In ethanol; chloroform; water for 4h; Irradiation;	92%

: 135-48-8
pentacene

: 1210054-89-9
C11H9FO3

: C33H23FO3

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	92%

: 135-48-8
pentacene

: 107969-78-8, 6395-86-4
methyl 4-phenyl-2-oxo-3-butenoate

: C33H24O3

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	91%

: 16767-75-2
N-sulphinylacetamide

: 135-48-8
pentacene

: C24H17NO2S

Conditions

Conditions	Yield
With methyltrioxorhenium(VII) In chloroform Heating;	90%

: 135-48-8
pentacene

: 100518-76-1
methyl (phenylmethylidene)pyruvate

: C34H26O3

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	89%

: 135-48-8
pentacene

: 1201664-47-2
C15H12O3

: C37H26O3

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	89%

: 872-36-6
vinylene carbonate

: 135-48-8
pentacene

: C25H16O3

Conditions

Conditions	Yield
In xylene at 180℃; for 72h; Diels-Alder reaction;	88%
In xylene at 170℃; Diels-Alder reaction;	80%

: 135-48-8
pentacene

: 128374-11-8
5,15-bis(4′-methoxyphenyl)porphyrin

: C56H40N4O2

Conditions

Conditions	Yield
In various solvent(s) at 200℃; Addition;	87%

: 135-48-8
pentacene

: 1-(4-Methoxy-2-methyl-phenyl)-pyrrole-2,5-dione

: C34H25NO3

Conditions

Conditions	Yield
In toluene at 100℃; for 5h; Diels-Alder Cycloaddition; Sealed tube; Inert atmosphere;	84%

: 960382-66-5
C11H9FO3

: 135-48-8
pentacene

: C33H23FO3

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	84%

: 123-73-9
trans-Crotonaldehyde

: 135-48-8
pentacene

: C26H20O

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	84%

: 135-48-8
pentacene

: 25440-14-6
tetrakis(pentafluorophenyl)porphyrin

: C66H24F20N4

Conditions

Conditions	Yield
In various solvent(s) at 200℃; Diels-Alder reaction; microwave irradiation;	83%
In various solvent(s) at 200℃; Addition;	60%

: 135-48-8
pentacene

: 670-54-2
ethenetetracarbonitrile

: C28H14N4

Conditions

Conditions	Yield
In toluene at 100℃; for 3h; Diels-Alder reaction; Inert atmosphere;	82%

: 1080-52-0
N-(2,4-dimethyl-phenyl)-maleimide

: 135-48-8
pentacene

: C34H25NO2

Conditions

Conditions	Yield
In toluene at 100℃; for 5h; Diels-Alder Cycloaddition; Sealed tube; Inert atmosphere;	81%

: 135-48-8
pentacene

: C13H8F3NO4

: C35H22F3NO4

Conditions

Conditions	Yield
In toluene for 12h; Diels-Alder Cycloaddition; Reflux;	80%

: 135-48-8
pentacene

: 68968-90-1
4-Biphenyliden-2-keto-propionsaeuremethylester

: C39H28O3

Conditions

Conditions	Yield
With bromo-triphenyl-methane; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 50℃; for 24h; Diels-Alder Cycloaddition; diastereoselective reaction;	79%

Pentacene Chemical Properties

Molecular Structure of Pentacene (CAS NO.135-48-8):

IUPAC Name: pentacene
Empirical Formula: C₂₂H₁₄
Molecular Weight: 278.3466
EINECS: 205-193-7
Flash Point: 264.5 °C
Storage temp: 0-6°C
Density: 1.232 g/cm³
Melting Point: >300 °C(lit.)
Water Solubility: insoluble
Index of Refraction: 1.811
Enthalpy of Vaporization: 76.86 kJ/mol
Boiling Point: 524.7 °C at 760 mmHg
Vapour Pressure: 1.41E-10 mmHg at 25°C
Appearance: solid Visual appearance of the given substance.
Stability: Stable, but air and light sensitive. Incompatible with strongoxidizing agents
Synonyms: Lin-dibenzanthracene ; Pentacene ; Lin-naphthoanthracene ; Benzo[b]naphthacene ; 2,3,6,7-Dibenzanthracene ; 2,3,6,7-Dibenzoanthracene ; Pentacene, sublimed ; Pentacene, for fluorescence
Product Categories: Miscellaneous;electronic; Electronic Chemicals; Functional Materials; Highly Purified Reagents; Organic Semiconducting Materials; Other Categories; Refined Products by Sublimation; Photoluminescent Materials > Light-Emitting Dopants and Fluorescent DyesOrganic Conductors and Photovoltaics

Pentacene Uses

Pentacene (CAS NO.135-48-8) have been examined as potential dichroic dyes. The pentacenoquinone displayed below is fluorescent and when mixed with liquid crystal E7 mixture a dichroic ratio of 8 is reached. The longer the acene the better it is able to align itself in a nematic liquid crystal phase. Combined with buckminsterfullerene, pentacene is used in the development of organic photovoltaic devices. Pentacene is a promising candidate for the use in organic thin film transistors and OFETs. It is one of the most thoroughly investigated conjugated organic molecules with a high application potential due to a hole mobility in OFETs of up to 5.5 cm2V-1s-1, which is comparable to that of amorphous silicon.

Pentacene Toxicity Data With Reference

dnd-mam:lym 20 mg

BIPMAA Biopolymers. 4 (1966),409.

Pentacene Consensus Reports

Reported in EPA TSCA Inventory.

Pentacene Safety Profile

Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of Pentacene (CAS NO.135-48-8):
Safety Statements: 24/25
24/25: Avoid contact with skin and eyes
WGK Germany: 3
F:8-10-23
F8: Photosensitive
F10: Keep under argon.
F23: Sensitive to air.

Product Name

Pentacene

Synthetic route

Pentacene Chemical Properties

Pentacene Uses

Pentacene Toxicity Data With Reference

Pentacene Consensus Reports

Pentacene Safety Profile

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