Naphthacene supplier | CasNO.92-24-0

Name
Naphthacene
EINECS 202-138-9
CAS No. 92-24-0
Article Data54
CAS DataBase
Density 1.19g/cm³
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
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
Hazard Symbols
Synonyms 2,3-Benzanthracene;2,3-Benzanthrene; Benz[b]anthracene; Chrysogen; Rubene; Tetracene; Tetracene(hydrocarbon)
PSA 0.00000
LogP 5.14620

Synthetic route

: 256439-93-7
2,3-diethynyl-anthracene

: 92-24-0
Tetracen

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 2,3-dibenzylfumaraldehyde

: 92-24-0
Tetracen

Conditions

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

: tetracene

: 92-24-0
Tetracen

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With zinc
With copper; zinc

: 13214-70-5
2,3-dibromonaphthalene

A: 92-24-0
Tetracen

B dihydrotetracene: dihydrotetracene

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 81 percent / PdCl2dppf / diethyl ether / Heating 2: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 3: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 4: PdCl2dppf / diethyl ether / Heating 5: NaH; MeOH / tetrahydrofuran / 2 h 6: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 6 steps 1: 81 percent / PdCl2dppf / diethyl ether / Heating 2: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 3: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 4: 86 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 5: NaH; MeOH / tetrahydrofuran / 2 h 6: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 6 steps 1: 81 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 2: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 3: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 4: PdCl2dppf / diethyl ether / Heating 5: NaH; MeOH / tetrahydrofuran / 2 h 6: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 6 steps 1: 81 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 2: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 3: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 4: 86 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 5: NaH; MeOH / tetrahydrofuran / 2 h 6: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme

: 73392-23-1
1,2-bis(trimethylsilylethynyl)benzene

A: 92-24-0
Tetracen

B dihydrotetracene: dihydrotetracene

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 100 percent / NBS; AgNO3 / acetone / 10 h / 25 °C 2: 70 percent / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 18100.7 Torr 3: 81 percent / PdCl2dppf / diethyl ether / Heating 4: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 5: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 6: PdCl2dppf / diethyl ether / Heating 7: NaH; MeOH / tetrahydrofuran / 2 h 8: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 8 steps 1: 100 percent / NBS; AgNO3 / acetone / 10 h / 25 °C 2: 70 percent / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 18100.7 Torr 3: 81 percent / PdCl2dppf / diethyl ether / Heating 4: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 5: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 6: 86 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 7: NaH; MeOH / tetrahydrofuran / 2 h 8: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 8 steps 1: 100 percent / NBS; AgNO3 / acetone / 10 h / 25 °C 2: 70 percent / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 18100.7 Torr 3: 81 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 4: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 5: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 6: PdCl2dppf / diethyl ether / Heating 7: NaH; MeOH / tetrahydrofuran / 2 h 8: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 8 steps 1: 100 percent / NBS; AgNO3 / acetone / 10 h / 25 °C 2: 70 percent / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 18100.7 Torr 3: 81 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 4: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 5: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 6: 86 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 7: NaH; MeOH / tetrahydrofuran / 2 h 8: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme

: 256439-90-4
1,2-bis(bromoethynyl)benzene

A: 92-24-0
Tetracen

B dihydrotetracene: dihydrotetracene

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 70 percent / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 18100.7 Torr 2: 81 percent / PdCl2dppf / diethyl ether / Heating 3: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 4: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 5: PdCl2dppf / diethyl ether / Heating 6: NaH; MeOH / tetrahydrofuran / 2 h 7: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 7 steps 1: 70 percent / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 18100.7 Torr 2: 81 percent / PdCl2dppf / diethyl ether / Heating 3: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 4: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 5: 86 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 6: NaH; MeOH / tetrahydrofuran / 2 h 7: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 7 steps 1: 70 percent / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 18100.7 Torr 2: 81 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 3: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 4: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 5: PdCl2dppf / diethyl ether / Heating 6: NaH; MeOH / tetrahydrofuran / 2 h 7: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 7 steps 1: 70 percent / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 18100.7 Torr 2: 81 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 3: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 4: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 5: 86 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 6: NaH; MeOH / tetrahydrofuran / 2 h 7: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme

: 96965-79-6
2,7-dibromo-3,6-dihydroxy naphthalene

: 92-24-0
Tetracen

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 77 percent / 10percent aq. NaOH / acetone / 0 °C 2: 40 percent / phenyllithium / tetrahydrofuran; cyclohexane; diethyl ether / Ambient temperature 3: 80 percent / MeOH, Mg / 10percent Pd/C / Ambient temperature 4: 78 percent / trifluoroacetic acid (TFA) / CHCl3 / 1 h / Heating View Scheme

: 96965-71-8
1,4:7,10-diepoxy-1,4,7,10-tetrahydronaphthacene

: 92-24-0
Tetracen

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / MeOH, Mg / 10percent Pd/C / Ambient temperature 2: 78 percent / trifluoroacetic acid (TFA) / CHCl3 / 1 h / Heating View Scheme

: 96965-64-9
3,6-dibromo-2,7-bis<(p-tolylsulfonyl)oxy>naphthalene

: 92-24-0
Tetracen

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 40 percent / phenyllithium / tetrahydrofuran; cyclohexane; diethyl ether / Ambient temperature 2: 80 percent / MeOH, Mg / 10percent Pd/C / Ambient temperature 3: 78 percent / trifluoroacetic acid (TFA) / CHCl3 / 1 h / Heating View Scheme

: 117820-97-0
2,3-dibromoanthracene

A: 92-24-0
Tetracen

B dihydrotetracene: dihydrotetracene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: PdCl2dppf / diethyl ether / Heating 2: NaH; MeOH / tetrahydrofuran / 2 h 3: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 3 steps 1: 86 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 2: NaH; MeOH / tetrahydrofuran / 2 h 3: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme

: 2,3-bis(bromoethynyl)naphthalene

A: 92-24-0
Tetracen

B dihydrotetracene: dihydrotetracene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 2: PdCl2dppf / diethyl ether / Heating 3: NaH; MeOH / tetrahydrofuran / 2 h 4: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 4 steps 1: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 2: 86 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 3: NaH; MeOH / tetrahydrofuran / 2 h 4: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme

: 256439-91-5
2,3-bis[(trimethylsilyl)ethynyl]naphthalene

A: 92-24-0
Tetracen

B dihydrotetracene: dihydrotetracene

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 2: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 3: PdCl2dppf / diethyl ether / Heating 4: NaH; MeOH / tetrahydrofuran / 2 h 5: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme
Multi-step reaction with 5 steps 1: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 2: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 3: 86 percent / PdCl2dppf; BuLi; ZnCl2 / tetrahydrofuran; diethyl ether / 12 h / Heating 4: NaH; MeOH / tetrahydrofuran / 2 h 5: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme

: 256439-92-6
2,3-bis(trimethylsilylethynyl)anthracene

A: 92-24-0
Tetracen

B dihydrotetracene: dihydrotetracene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaH; MeOH / tetrahydrofuran / 2 h 2: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme

: 856208-24-7
5,12-dihydro-naphthacen-5-ol

: 92-24-0
Tetracen

Conditions

Conditions	Yield
With ethanol; mineral acid

: 581-40-8
2,3-dimethylnaphthalene

: 92-24-0
Tetracen

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3; carbon disulfide 2: 415 °C View Scheme

polystyrene: polystyrene

A: 239-01-0
11H-benzo[a]carbazole

B: 207-08-9
Benzo[k]fluoranthene

C: 92-24-0
Tetracen

D: 27208-37-3
cyclopenta[c,d]pyrene

Conditions

Conditions	Yield
With air at 900℃; Condensation; combustion; pyrolysis; PAH formation; Formation of xenobiotics; Further byproducts given. Title compound not separated from byproducts;	A 0.21 mg B 0.04 mg C 0.45 mg D 0.03 mg

...Expand

: 13214-70-5
2,3-dibromonaphthalene

: 92-24-0
Tetracen

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 52 percent / PhLi / tetrahydrofuran; cyclohexane / 1 h / 25 °C 2: 85 percent / m-CPBA / acetonitrile / 2 h / Heating View Scheme

: 80789-65-7
10-bromo-1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-1,4;5,8-dimethanotriphenylene

: 92-24-0
Tetracen

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 74 percent / Fe powder, Br2 / various solvent(s) / 2 h / Heating 2: 63 percent 3: 52 percent / PhLi / tetrahydrofuran; cyclohexane / 1 h / 25 °C 4: 85 percent / m-CPBA / acetonitrile / 2 h / Heating View Scheme

: 67102-98-1
10,11-dibromo-1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-1,4;5,8-dimethanotriphenylene

: 92-24-0
Tetracen

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 63 percent 2: 52 percent / PhLi / tetrahydrofuran; cyclohexane / 1 h / 25 °C 3: 85 percent / m-CPBA / acetonitrile / 2 h / Heating View Scheme

: 2,3-dibenzylfumaraldehyde

A: 92-24-0
Tetracen

B: C18H16

Conditions

Conditions	Yield
Stage #1: 2,3-dibenzylfumaraldehyde With indium(III) triflate In 1,2-dichloro-ethane at 65℃; for 1.5h; Microwave irradiation; Stage #2: In 1,2-dichloro-ethane at 115℃; for 0.5h; Microwave irradiation; regiospecific reaction;

: 13209-15-9
1,2-bis(dibromomethyl)benzene

A: 92-24-0
Tetracen

B zinc dust: zinc dust

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaI / dimethylformamide 2: 1.) diborane, 2.) oxidizing agent / 1.) diglyme View Scheme

: 130-15-4
[1,4]naphthoquinone

A: 92-24-0
Tetracen

B zinc dust: zinc dust

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaI / dimethylformamide 2: 1.) diborane, 2.) oxidizing agent / 1.) diglyme View Scheme

: 71038-78-3
5,11-dichlorotetracene

A: 1090-13-7
5,12-naphthacenequinone

B: 92-24-0
Tetracen

Conditions

Conditions	Yield
With potassium hydroxide at 150 - 160℃;

: 92-24-0
Tetracen

: 959-02-4
5,12-dihydro-naphthacene

Conditions

Conditions	Yield
With hydrogen iodide; acetic acid for 120h; Heating;	99%
With tris(pentafluorophenyl)borate; hydrogen; (pentafluorophenyl)diphenylphosphine In 1,2-dichloro-ethane at 80℃; under 61506.2 Torr; for 10h;	90%
With Dicalcium Nitride Electride In tetrahydrofuran; isopropyl alcohol at 65℃; for 24h; Birch Reduction; Inert atmosphere;	82%

: samarocene

: 92-24-0
Tetracen

: C58H72Sm2

Conditions

Conditions	Yield
In toluene under N2 or Ar; 2,3-benzanthracene was added to the samarocene in toluene, stirred for 5 min; solvent was removed by rotary evapn.; elem. anal.;	98%

: 872-36-6
vinylene carbonate

: 92-24-0
Tetracen

: 71440-73-8, 79982-79-9, 80009-62-7
5,12-dihydro-5,12-ethanonaphthacene-cis-13,14-diyl carbonate

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 180℃; for 72h; Diels-Alder Cycloaddition; Autoclave;	95%
for 8h; Heating;	11%

: 92-24-0
Tetracen

: 40577-78-4
5,11-dibromonaphthacene

Conditions

Conditions	Yield
With N-Bromosuccinimide In chloroform; N,N-dimethyl-formamide at 60℃; for 5h;	92%
With N-Bromosuccinimide In chloroform; N,N-dimethyl-formamide at 60℃; for 5h;	92%
With N-Bromosuccinimide In chloroform at 60℃;	48%

: 92-24-0
Tetracen

: C54H47B2ClN4

: C72H59B2ClN4

Conditions

Conditions	Yield
In benzene-d6 at 60℃; for 12h; Inert atmosphere; regioselective reaction;	92%

: 92-24-0
Tetracen

: 23790-75-2
5-bromotetracene

Conditions

Conditions	Yield
With N-Bromosuccinimide In chloroform; N,N-dimethyl-formamide	90%
With N-Bromosuccinimide In chloroform at 60℃; for 3h;	90%
With N-Bromosuccinimide In dichloromethane; N,N-dimethyl-formamide at 50℃; Inert atmosphere; Darkness;	88%

: 92-24-0
Tetracen

: 193-44-2
tetrathiatetracene

Conditions

Conditions	Yield
With sulfur In N,N-dimethyl-formamide at 155℃; for 5h; Inert atmosphere;	86%
With sulfur; 1,2,3-trichlorobenzene
With disulfur dichloride; 1,2,3-trichlorobenzene
Multi-step reaction with 2 steps 1: chlorobenzene; S2cl2 2: trichlorobenzene; sulfur View Scheme

: 92-24-0
Tetracen

: 670-54-2
ethenetetracarbonitrile

: 23790-72-9
13,13,14,14-tetracyano-5,12-dihydro-5,12-ethano-naphthacene

Conditions

Conditions	Yield
In toluene at 120℃; for 20h; Diels-Alder Cycloaddition; Inert atmosphere; Darkness; Sealed tube;	84%

: 92-24-0
Tetracen

: C12H20N3S(1+)*F6Sb(1-)

: 173471-00-6
5-cyanotetracene

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;	84%
With boron trifluoride diethyl etherate at 80℃; for 16h;	84%

: 156-60-5
trans-1,2-dichloroethylene

: 92-24-0
Tetracen

: 87567-71-3
trans-7,8-dichloro-2,3-(2',3'-naphtho)-5,6-benzobicyclo<2.2.2>octa-2,5-diene

Conditions

Conditions	Yield
at 153℃; for 40h;	79%

: 92-24-0
Tetracen

: 1090-13-7
5,12-naphthacenequinone

Conditions

Conditions	Yield
With iodosylbenzene sulfate; cobalt(II) 5,10,15,20-tetraphenylporphyrin In dichloromethane at 25℃; for 2h; Inert atmosphere;	77%
With oxygen In benzene for 17h; Irradiation;	36%
With air; xylene UV-Licht oder Gluehlampenlicht;

: 92-24-0
Tetracen

: [Pd3(μ3-anisole)(μ3-C8H8)(CH3CN)3][BF4]2

: [Pd3(μ3-tetracene)(μ3-cyclooctatetraene)(CH3CN)][BF4]2

Conditions

Conditions	Yield
In nitromethane at 80℃; for 1h; Inert atmosphere;	76%

: 1580-18-3
1,2,3,4,5,6,7,8-octafluoroanthracene-9,10-dione

: 92-24-0
Tetracen

: C14F8O2*C18H12

Conditions

Conditions	Yield
In toluene at 105℃; for 0.5h;	71%

: 92-24-0
Tetracen

: 16218-39-6
1,2,3,4,7,8,9,10-octahydrotetracene

Conditions

Conditions	Yield
With tetrahydrofuran; chromium chloride; methylmagnesium bromide; hydrogen; 1,2-bis(2,6-diisopropylphenylimino)ethane at 0 - 20℃; under 37503.8 Torr; for 24h; Autoclave; regioselective reaction;	69%

: 92-24-0
Tetracen

: 400090-79-1
5-[2,4,6-tris-(bis-trimethylsilanyl-methyl)-phenyl]-dibenzo[b,e]siline

: C58H80Si7

Conditions

Conditions	Yield
In benzene-d6 at 80℃; for 24h; Inert atmosphere;	68%

: 92-24-0
Tetracen

: 3709-20-4
dimethyl 2-phenyl-1,1-cyclopropanedicarboxylate

: 1095968-29-8
dimethyl 21-phenylpentacyclo[10.6.3.0(2,11).0(4,9).0(13,18)]henicosa-2,4,6,8,10,13,15,17-octaene-19,19-dicarboxylate

Conditions

Conditions	Yield
With tin(IV) chloride In dichloromethane at -40 - 20℃; for 23.5h; Inert atmosphere;	65%

: 930-88-1
N-methylmaleimide

: 92-24-0
Tetracen

: 67041-56-9, 67111-65-3
N-Methyl-5,12-ethano-5,12-dihydronaphthacen-13,14-dicarboximid

Conditions

Conditions	Yield
In toluene at 120℃; for 24h; Diels-Alder Cycloaddition; Inert atmosphere; Darkness; Sealed tube;	62%

: [(η5-Me5C5)Co]2-μ-(η4:η4-toluene)

: 92-24-0
Tetracen

: 656821-03-3
[(bis(η5-pentamethylcyclopentadienyl)cobalt):μ:(η4:1,4 η4:7,10-tetracene)]

Conditions

Conditions	Yield
In benzene under inert gas; soln. of Co-complex and tetracene in benzene stirred for 3 h; evapd., residue dissolved in Et2O, cooled to 0°C; elem. anal.;	61%

: 108-31-6
maleic anhydride

: 92-24-0
Tetracen

: 5,12-dihydro-5,12-ethano-naphthacene-13,14-dicarboxylic acid anhydride

Conditions

Conditions	Yield
In toluene at 120℃; for 8h; Diels-Alder Cycloaddition; Inert atmosphere; Darkness; Sealed tube;	60%
With xylene
In various solvent(s) at 91.5℃; Rate constant;
In various solvent(s) at 91.5℃; Mechanism; Rate constant; analogous reaction of other polycyclic aromatic hydrocarbons; structure/reactivity correlations, application of theoretical models;

: 92-24-0
Tetracen

: 764-42-1
1,2-Dicyanoethylene

: 13,14-dicyano-5,12-dihydro-5,12-ethano-naphthacene

Conditions

Conditions	Yield
In toluene at 150℃; for 42h; Diels-Alder Cycloaddition; Inert atmosphere; Darkness; Sealed tube;	55%

: 92-24-0
Tetracen

: 56922-55-5, 77210-02-7
C36H24

Conditions

Conditions	Yield
In benzene for 20h; Irradiation;	54%
In benzene for 20h; Product distribution; Irradiation;

: 79-37-8
oxalyl dichloride

: 92-24-0
Tetracen

: 1334510-66-5
acetetracenylene-1,2-dione

Conditions

Conditions	Yield
With aluminum (III) chloride In 1,2-dichloro-benzene at 20℃; for 12h; Friedel Crafts acylation; Inert atmosphere;	54%
With aluminum (III) chloride In 1,2-dichloro-benzene at 0 - 25℃; for 18h; Inert atmosphere;	52%

: 92-24-0
Tetracen

: C10H20N6(2+)*2BF4(1-)

: C28H32N6(2+)*2BF4(1-)

Conditions

Conditions	Yield
In acetonitrile for 36h; Diels-Alder Cycloaddition; Schlenk technique; Inert atmosphere;	53%

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.

Product Name

Naphthacene

Synthetic route

Naphthacene Chemical Properties

Naphthacene Uses

Naphthacene Toxicity Data With Reference

Naphthacene Consensus Reports

Naphthacene Safety Profile

Naphthacene Specification

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