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Naphthacene

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Name

Naphthacene

EINECS 202-138-9
CAS No. 92-24-0 Density 1.19g/cm3
PSA 0.00000 LogP 5.14620
Solubility 1.507ug/L(25 oC) Melting Point >300 °C(lit.)

Formula C18H12 Boiling Point 436.7°C at 760 mmHg
Molecular Weight 228.293 Flash Point 209.1°C
Transport Information N/A Appearance orange powder
Safety Mutation data reported. Explosion hazard; shock will explode it. Can react on contact with oxidizing materials. When heated to decomposition it emits acrid smoke and irritating fumes. Risk Codes R50/53   
Molecular Structure Molecular Structure of 92-24-0 (Naphthacene) Hazard Symbols
Synonyms

2,3-Benzanthracene;2,3-Benzanthrene; Benz[b]anthracene; Chrysogen; Rubene; Tetracene; Tetracene(hydrocarbon)

Article Data 54

Naphthacene Synthetic route

256439-93-7

2,3-diethynyl-anthracene

92-24-0

Tetracen

Conditions
ConditionsYield
With cyclohexa-1,4-diene In benzene at 160℃; under 12411.9 Torr; cycloaromatization;64%

5,12-dihydrotetracene-5,12-diol

92-24-0

Tetracen

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; water for 1h; Inert atmosphere;71.5%
959-02-4

5,12-dihydro-naphthacene

92-24-0

Tetracen

Conditions
ConditionsYield
palladium on activated charcoal In xylene for 48h; Heating;95%
With chloranil; acetic acid
at 220℃; Erhitzen unter Durchleiten von Luft;
With copper at 400℃;
3073-99-2

5,12-(H)-Naphthacenone

92-24-0

Tetracen

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Ambient temperature;83%
Multi-step reaction with 2 steps
1: aq.-ethanolic NaOH; zinc-powder
2: mineral acid; ethanol
View Scheme
85894-23-1

13-methyl-5,12-dihydronaphthacen-5,12-imine

92-24-0

Tetracen

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In acetonitrile for 2h; Heating;85%
96965-72-9

1,4:7,10-diepoxy-1,2,3,4,7,8,9,10-octahydronaphthacene

92-24-0

Tetracen

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform for 1h; Heating;78%

2,3-dibenzylfumaraldehyde

92-24-0

Tetracen

Conditions
ConditionsYield
With titanium tetrachloride In 1,2-dichloro-ethane at 40℃; for 3h; Reagent/catalyst; Temperature; Reflux;72%

tetracene

92-24-0

Tetracen

Conditions
ConditionsYield
With pyrographite In benzene at 80℃; under 760.051 Torr; for 72h; Sealed tube; Darkness;23.2 mg
1090-13-7

5,12-naphthacenequinone

92-24-0

Tetracen

Conditions
ConditionsYield
With oxidizing agent; diborane 1.) diglyme; Multistep reaction;
Multi-step reaction with 2 steps
1: aq.-ethanolic NaOH; zinc-powder
2: mineral acid; ethanol
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C / Inert atmosphere
2: hydrogenchloride; tin(ll) chloride / tetrahydrofuran; water / 1 h / Inert atmosphere
View Scheme
7.8.9.10-tetrahydro-naphthacenequinone-(5.12)

7.8.9.10-tetrahydro-naphthacenequinone-(5.12)

92-24-0

Tetracen

Conditions
ConditionsYield
With zinc
With copper; zinc

Naphthacene Chemical Properties

Chemistry informtion about  Naphthacene (92-24-0) is:
IUPAC Name: Tetracene
Synonyms: Tetracene ; Naphthacene ; Naphthycene ; 2,3-Benzanthrene ; Chrysogen ; Methacene ; Rubene ; Tetracen
MF: C18H12
MW: 228.29
EINECS: 202-138-9
Melting Point: >300 °C(lit.)
Flash Point: 209.1 °C
Boiling Point: 436.7 °C at 760 mmHg
Density: 1.19 g/cm3 
Enthalpy of Vaporization: 66.65 kJ/mol
Vapour Pressure: 2.02E-07 mmHg at 25°C
Following is the molecular structure of  Naphthacene (92-24-0) is:

Naphthacene Uses

 Naphthacene (92-24-0) is a molecular organic semiconductor, used in organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs). It can be also used as a gain medium in dye lasers as a sensitiser in chemoluminescence.

Naphthacene Toxicity Data With Reference

1.    

mma-sat 5 µmol/L

    ENMUDM    Environmental Mutagenesis. 3 (1981),11.
2.    

dns-rat:lvr 500 µmol/L

    ENMUDM    Environmental Mutagenesis. 3 (1981),11.

Naphthacene Consensus Reports

Reported in EPA TSCA Inventory.

Naphthacene Safety Profile

Mutation data reported. Explosion hazard; shock will explode it. Can react on contact with oxidizing materials. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:
Xn: Harmful
Risk Statements:
R40: Limited evidence of a carcinogenic effect.
Safety Statements:
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37: Wear suitable protective clothing and gloves.
WGK Germany: 3
RTECS: QI7605000

Naphthacene Specification

About  Naphthacene (92-24-0),its appearance is orange powder.It is stable and incompatible with strong oxidizing agents,also,chemical stability occurs when a substance is in a (dynamic) chemical equilibrium with its environment.

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