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Name	Pentacene	EINECS	205-193-7
CAS No.	135-48-8	Density	1.232 g/cm³
PSA	0.00000	LogP	6.29940
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	N/A	Appearance	solid
Safety	24/25	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	2,3:6,7-Dibenzanthracene;Benzo[b]naphthacene;Dibenz[b,i]anthracene;NSC 90784;lin-Dibenzanthracene;lin-Naphthoanthracene;	Article Data	40

Pentacene 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

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.

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