Conditions | Yield |
---|---|
at 780℃; under 0.2 Torr; for 4h; flash vacuum pyrolysis; | 85% |
at 800℃; Inert atmosphere; Schlenk technique; Pyrolysis; | 82% |
at 800℃; under 0.375038 Torr; Pyrolysis; | 45% |
at 780℃; under 0.3 Torr; Cyclization; | |
at 780℃; under 0.3 Torr; |
Conditions | Yield |
---|---|
at 647℃; under 0.08 Torr; | A 3% B 77% |
at 647℃; | A 2 % Chromat. B 80 % Chromat. |
(Z)-3,4-diethylhexa-1,5-diyn-3-ene
A
styrene
B
tetralin
C
benzocyclobutene
D
cis-5-decene-3,7-diyne
Conditions | Yield |
---|---|
at 500℃; Further byproducts given; | A 1.3% B 1.6% C 7.8% D 76.8% |
(Z)-3,4-diethylhexa-1,5-diyn-3-ene
A
tetralin
B
2-ethylstyrene
C
benzocyclobutene
D
cis-5-decene-3,7-diyne
Conditions | Yield |
---|---|
at 500℃; Further byproducts given; | A 1.6% B 7.8% C 7.8% D 76.8% |
at 500℃; Further byproducts given; | A 1.6% B 8.8% C 7.8% D n/a |
Conditions | Yield |
---|---|
With magnesium at 600℃; | A 15% B 73% |
2-methylbenzyl bromide
A
o-xylene
B
benzocyclobutene
C
1,2-bis(2-methylphenyl)ethane
D
(E)-2,2'-dimethylstilbene
Conditions | Yield |
---|---|
With magnesium at 600℃; under 0.15 Torr; | A n/a B n/a C 70% D n/a |
[2.2]Paracyclophan
A
styrene
B
para-xylene
C
benzocyclobutene
D
toluene
E
benzene
Conditions | Yield |
---|---|
at 970℃; Product distribution; | A 55% B 31% C 4% D 3% E 4% |
at 930℃; under 0.1 Torr; Product distribution; Mechanism; detected by 13C nmr; |
[2.2]Paracyclophan
A
styrene
B
para-xylene
C
benzocyclobutene
D
benzene
Conditions | Yield |
---|---|
at 930℃; Further byproducts given; | A 55% B 31% C 4% D 4% |
1,2-bis[(phenylseleno)methyl]benzene
A
1,3-dihydro-2-benzoselenophene
B
benzocyclobutene
C
anthracene
D
diphenyl diselenide
Conditions | Yield |
---|---|
at 600℃; under 20 Torr; for 0.0333333h; Further byproducts given; | A 38% B 7% C 16% D 47% |
at 600℃; under 20 Torr; Further byproducts given; | A 38% B 7% C 18% D 47% |
1,1-Dichlorobenzocyclobutene
benzocyclobutene
Conditions | Yield |
---|---|
With ammonia; lithium; isopropyl alcohol In diethyl ether at -60 - -40℃; for 6h; | 46% |
1,2-bis[(phenylseleno)methyl]benzene
A
1,3-dihydro-2-benzoselenophene
B
benzocyclobutene
C
diphenyl diselenide
Conditions | Yield |
---|---|
at 600℃; under 8 Torr; for 0.0333333h; | A 13% B 40% C 42% |
at 600℃; under 8 Torr; | A 13% B 40% C 40% |
Conditions | Yield |
---|---|
at 770℃; | A 41 % Chromat. B 30% |
bis-<2-(methylthio)benzyl> oxalate
A
2,3-dihydrobenzo(b)thiophene
B
1,3-Dihydrobenzothiophen
C
benzocyclobutene
D
anthracene
E
methyl o-tolyl sulfide
F
C8H9S
Conditions | Yield |
---|---|
at 800℃; under 0.001 Torr; for 1.66667h; Product distribution; | A 8% B 11% C 29% D 6% E 3% F n/a |
bis-<2-(methylthio)benzyl> oxalate
A
2,3-dihydrobenzo(b)thiophene
B
1,3-Dihydrobenzothiophen
C
benzocyclobutene
D
methyl o-tolyl sulfide
Conditions | Yield |
---|---|
at 800℃; under 0.001 Torr; for 1.66667h; Further byproducts given; | A 8% B 11% C 29% D n/a |
2-methylphenyl acetate
A
styrene
B
2-Ethyltoluene
C
benzocyclobutene
Conditions | Yield |
---|---|
at 691℃; | A 1 % Chromat. B 25 % Chromat. C 28% |
at 691℃; | A 1 % Chromat. B 25 % Chromat. C 28 % Chromat. |
4,5-Dihydrocycloocta-1,2,3-selenadiazol
A
2,3-Dihydrobenzoselenophene
B
benzocyclobutene
Conditions | Yield |
---|---|
copper at 180℃; under 20 Torr; | A 16% B 24% |
Conditions | Yield |
---|---|
at 400℃; | A 21% B 20% |
at 375℃; flash vacuum thermolysis; Yield given. Title compound not separated from byproducts; |
Lithium Salt of Benzocyclobutenone Tosylhydrazone
A
benzocyclobutenone
B
o-xylene
C
2-Methylbenzonitrile
D
benzocyclobutene
E
cis-1-(1-benzocyclobutenylidene)benzocyclobutene
F
trans-1-(1-Benzocyclobutenylidene)benzocyclobutene
Conditions | Yield |
---|---|
at 350 - 370℃; under 0.05 - 0.1 Torr; for 2h; Product distribution; | A 5% B 1% C 5% D 1% E n/a F n/a |
1,3-dihydrobenzo[c]thiophene-2,2-dioxide
A
o-xylene
B
benzocyclobutene
C
5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene
Conditions | Yield |
---|---|
at 280℃; |
Conditions | Yield |
---|---|
at 460 - 770℃; unter Stickstoff.Pyrolysis; | |
With chromium-promoted Raney-nickel at 460 - 770℃; Pyrolysis; | |
at 362℃; |
1-chloro-1,2-dihydrobenzocyclobutene
benzocyclobutene
Conditions | Yield |
---|---|
With palladium on activated charcoal Hydrogenation; |
Conditions | Yield |
---|---|
With palladium on activated charcoal; sodium ethanolate Hydrogenation; | |
With lithium aluminium tetrahydride |
7,8-Dibromobicyclo<4.2.0>octa-1,3,5-trien
benzocyclobutene
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride |
Conditions | Yield |
---|---|
at 685℃; |
Conditions | Yield |
---|---|
at 570℃; |
Conditions | Yield |
---|---|
With tetramethyl-2,2,3,3 butane at 733.9℃; under 1520 - 2280 Torr; Kinetics; Rate constant; homogenous gas-phase decyclization; other hydrocarbons as reaction partners, other temperature; |
tetralin
A
styrene
B
1-methyl-2-(2-propenyl)-benzene
C
1,2-Dihydronaphthalene
D
benzocyclobutene
E
phenylacetylene
F
1-indene
Conditions | Yield |
---|---|
In gas under 0.3 Torr; Product distribution; Mechanism; Irradiation; laser-induced decomposition, multiphoton excitation, energy/pulse 0.4 J, 13020 pulses; |
tetralin
A
styrene
B
1-methyl-2-(2-propenyl)-benzene
C
naphthalene
D
1,2-Dihydronaphthalene
E
benzocyclobutene
F
1-indene
Conditions | Yield |
---|---|
In gas at 750℃; Product distribution; Mechanism; flow pyrolysis, further temperatures, pressure, SiF4 sensitization; | |
silicon tetrafluoride Product distribution; Mechanism; Irradiation; various laser excitation energy, various deuterium-labelled tetralins; |
tetralin
A
styrene
B
1-methyl-2-(2-propenyl)-benzene
C
1,2-Dihydronaphthalene
D
1-methyl-2-vinyl-benzene
E
benzocyclobutene
F
1-indene
Conditions | Yield |
---|---|
With methane at 1093.9℃; under 1520 - 2280 Torr; Product distribution; Mechanism; Kinetics; homogenous gas-phase decyclization; other hydrocarbons as reaction partners; var. concs. of tetralin; other temperatures; | A 8.53 % Chromat. B 4.43 % Chromat. C 2.80 % Chromat. D 1.82 % Chromat. E 15.3 % Chromat. F 2.38 % Chromat. |
tetralin
A
styrene
B
naphthalene
C
1,2-Dihydronaphthalene
D
benzocyclobutene
E
1-indene
Conditions | Yield |
---|---|
at 888℃; under 0.1 Torr; Product distribution; other temp.; |
benzocyclobutene
(9S,10S)-(-)-Dimethyl 9,10-Dihydro-9,10-ethenoanthracene-1,5-dicarboxylate
(5S,12S)-(-)-dimethyl 5,5a,6,11,11a,12-hexahydro-5,12<1',2'>benzenonaphthacene-1,15-dicarboxylate
Conditions | Yield |
---|---|
In toluene at 250℃; for 16h; sealed tube; | 100% |
chloro-trimethyl-silane
benzocyclobutene
2,5-Bis(trimethylsilyl)bicyclo<4.2.0>octa-1(6),3-diene
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran at 0 - 20℃; for 144h; | 98% |
With lithium In tetrahydrofuran at 0℃; for 4h; | 92% |
With Li (2percent Na) In tetrahydrofuran at 0 - 10℃; for 0.5h; | 91% |
With lithium |
tricarbonyl(naphthalene)chromium(0)
benzocyclobutene
cyclobutabenzenetricarbonylchromium(0)
Conditions | Yield |
---|---|
With THF In diethyl ether Cr-complex, benzocyclobutene and THF were heated in ether in a Carius tube under inert atmosphere at 70°C for 16 h; crystd. from octane; | 96% |
benzocyclobutene
N-acetyl-1,3-oxazol-2-one
(3aS,9aR)-3-Acetyl-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-d]oxazol-2-one
Conditions | Yield |
---|---|
In toluene at 230℃; for 48h; | 90% |
benzocyclobutene
6,7-dibromo-1,4-epoxy-1,4-dihydronaphthalene
2,3-dibromo-5,5a,6,11,11a,12-hexahydronaphthacene 5,12-endoxide
Conditions | Yield |
---|---|
In toluene at 190℃; for 24h; | 89% |
benzocyclobutene
1,4-dihydro-1,4-epoxyanthracene
5,5a,6,13,13a,14-hexahydropentacene 6,13-endoxide
Conditions | Yield |
---|---|
In toluene at 190℃; for 24h; | 87% |
benzocyclobutene
(1α,4α,5β,8β)-1,4,5,8-tetrahydro-1,4:5,8-diepoxyanthracene
C30H26O2
Conditions | Yield |
---|---|
In toluene at 185 - 195℃; for 24h; | 87% |
benzocyclobutene
(η6-benzocyclobutene)(η5-cyclopentadienyl)iron(II) hexafluorophosphate
Conditions | Yield |
---|---|
In further solvent(s) (N2); addn. of iron complex to a soln. of ligand in 1,2-dichloropropane,stirring for 3 h at 120°C; addn. of CH2Cl2 and n-hexane, filtration over Celite, washing with toluene, eluting with CH2Cl2, evapn.; elem. anal.; | 87% |
1,4-dihydronaphthalene-1,4-epoxide
benzocyclobutene
5,5a,6,11,11a,12-hexahydronaphthacene 5,12-endoxide
Conditions | Yield |
---|---|
In toluene at 190℃; for 24h; | 86% |
benzocyclobutene
(1α,4α,5α,8α)-1,4,5,8-tetrahydro-1,4:5,8-diepoxyanthracene
C30H26O2
Conditions | Yield |
---|---|
In toluene at 185 - 195℃; for 24h; | 84% |
Conditions | Yield |
---|---|
Stage #1: 4-methylbenzotrifluoride; benzocyclobutene With boron tribromide In dichloromethane at 25℃; for 3h; Inert atmosphere; Stage #2: With methanol In dichloromethane at 25℃; for 2h; Inert atmosphere; | 84% |
tris(ammonia)chromium tricarbonyl
benzocyclobutene
cyclobutabenzenetricarbonylchromium(0)
Conditions | Yield |
---|---|
In 1,4-dioxane 3 h reflux; | 80% |
In 1,4-dioxane boiling temperature; purified by sublimation (80 °C/0.001mbar); identity is verified by spectroscopic methods, MS, HRMS and elem. anal.; | 51% |
In 1,4-dioxane (Ar); addn. of Cr(CO)3(NH3)3 and dioxane to cyclobutabenzene; refluxed for 3.5 h; cooling to 25°C; removal of solvent in vac.; extn. with boiling pentane; filtration; stored at 30°C for 24 h and than at -78°C for 24 h; crystn.; dried in vac. at room temp.; recrystn.; stored at -30°C under Ar; elem. anal.; | 51% |
Conditions | Yield |
---|---|
With bromine In water at 20℃; for 4.5h; Reagent/catalyst; Cooling with ice; Darkness; | 76.9% |
With bromine; sodium dodecyl-sulfate In water at 0℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique; Darkness; | 67% |
With bromine; iodine; acetic acid In water at 0 - 20℃; | 51.1% |
1,3-diacetyl-2,3-dihydro-1H-imidazol-2-one
benzocyclobutene
(3aR,9aS)-1,3-Diacetyl-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-d]imidazol-2-one
Conditions | Yield |
---|---|
In toluene at 230℃; for 48h; | 74% |
benzocyclobutene
chromium(0) hexacarbonyl
cyclobutabenzenetricarbonylchromium(0)
Conditions | Yield |
---|---|
In not given according to method by C. A. L. Mahaffy and P. L. Pauson, Inorg. Synth., XIX (1979) 154; | 73% |
boiling;; | 40% |
boiling;; | 40% |
vinylene carbonate
benzocyclobutene
cis-1,4-dihydronaphthalene carbonate
Conditions | Yield |
---|---|
In toluene at 230℃; for 48h; | 70% |
In toluene at 230℃; for 48h; | 70% |
Dichloromethyl methyl ether
benzocyclobutene
bicyclo<4.2.0>octa-1,3,5-triene-3-carboxaldehyde
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at 0℃; for 1h; | 70% |
With titanium tetrachloride Formylation; | 34% |
With titanium tetrachloride In dichloromethane at 0℃; | 34% |
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene at 200℃; for 15.5h; | 70% |
benzocyclobutene
7,8-Dibromobicyclo<4.2.0>octa-1,3,5-trien
Conditions | Yield |
---|---|
With N-Bromosuccinimide In 1,2-dichloro-ethane at 120℃; for 48h; Inert atmosphere; | 70% |
benzene tricarbonylmolybdenum(0)
benzocyclobutene
tricarbonyl(η6-1,2-dihydrocyclobutabenzene)molybdenum
Conditions | Yield |
---|---|
In tetrahydrofuran (N2); Schlenk technique; Mo complex was added to soln. of arene (3 equiv.) in THF (3 equiv.); stirred at room temp. for 1 h; volatiles were removed (vac.); arene and THF were added; stirred at room temp. for 1 h; evapd.; dissolved in warm methylcyclohexane; filtered through Celite; solvent removed (vac.); | 69% |
benzocyclobutene
fullerene-C60
A
C75H10FNO3
Conditions | Yield |
---|---|
In various solvent(s) for 8h; Product distribution; Heating; futher o-quinodimethanes; | A 65% B n/a |
benzocyclobutene
(+/-)4-bromo-11-oxatricyclo[6.2.1.02,7]-undeca-2,4,6,9-tetraene
C18H15BrO
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene at 220℃; for 6h; sealed tube; | 64% |
benzocyclobutene
2-chloropropionyl chloride
1-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)-3-chloropropan-1-one
Conditions | Yield |
---|---|
With aluminum (III) chloride In nitromethane at 0 - 20℃; Friedel-Crafts acylation; Inert atmosphere; | 63% |
With aluminium trichloride; nitromethane |
maleic anhydride
benzocyclobutene
1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic acid anhydride
Conditions | Yield |
---|---|
In 1,3,5-trimethyl-benzene at 210℃; for 48h; autoclave; | 63% |
The Bicyclo[4.2.0]octa-1,3,5-triene, with the CAS registry number 694-87-1, is also called Benzocyclobutene. And the molecular formula of the chemical is C8H8. What's more, while dealing with this flammable chemical, you should be cautious: Keep away from sources of ignition and no smoking.
The characteristics of Bicyclo[4.2.0]octa-1,3,5-triene are as followings: (1)ACD/LogP: 2.78; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.78; (4)ACD/LogD (pH 7.4): 2.78; (5)ACD/BCF (pH 5.5): 75.73; (6)ACD/BCF (pH 7.4): 75.73; (7)ACD/KOC (pH 5.5): 770.53; (8)ACD/KOC (pH 7.4): 770.53; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 33.81 cm3; (15)Molar Volume: 100.7 cm3; (16)Polarizability: 13.4×10-24cm3; (17)Surface Tension: 39.9 dyne/cm; (18)Density: 1.033 g/cm3; (19)Flash Point: 40.1 °C; (20)Enthalpy of Vaporization: 38.43 kJ/mol; (21)Boiling Point: 164.3 °C at 760 mmHg; (22)Vapour Pressure: 2.6 mmHg at 25°C.
Uses of Bicyclo[4.2.0]octa-1,3,5-triene: It can react with chloro-trimethyl-silane to produce 2,5-Bis(trimethylsilyl)bicyclo[4.2.0]octa-1(6),3-diene. This reaction will need reagent Li, and the menstruum tetrahydrofuran. The reaction time is 4 hours with temperature of 0°C, and the yield is about 92%.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: c1cccc2c1CC2
(2)InChI: InChI=1/C8H8/c1-2-4-8-6-5-7(8)3-1/h1-4H,5-6H2
(3)InChIKey: UMIVXZPTRXBADB-UHFFFAOYAR
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