Product Name

  • Name

    Bicyclo[4.2.0]octa-1,3,5-triene

  • EINECS
  • CAS No. 694-87-1
  • Article Data70
  • CAS DataBase
  • Density 1.033 g/cm3
  • Solubility
  • Melting Point
  • Formula C8H8
  • Boiling Point 164.3 °C at 760 mmHg
  • Molecular Weight 104.152
  • Flash Point 40.1 °C
  • Transport Information UN 3295 3/PG 3
  • Appearance
  • Safety 16
  • Risk Codes 10
  • Molecular Structure Molecular Structure of 694-87-1 (Bicyclo[4.2.0]octa-1,3,5-triene)
  • Hazard Symbols R10:;
  • Synonyms 1,2-Dihydrobenzocyclobutene;1,2-Dihydrocyclobutabenzene;Benzocyclobutane;Benzocyclobutene, 1,2-dihydro-;Bicyclo[4.2.0]octa-2,4,6-triene;Cyclobutabenzene;Bicyclo(4.2.0)octa-1,3,5-triene;
  • PSA 0.00000
  • LogP 1.78520

Synthetic route

1-chloromethyl-2-methylbenzene
552-45-4

1-chloromethyl-2-methylbenzene

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
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;
1-chloromethyl-2-methylbenzene
552-45-4

1-chloromethyl-2-methylbenzene

A

styrene
292638-84-7

styrene

B

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
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
78091-33-5

(Z)-3,4-diethylhexa-1,5-diyn-3-ene

A

styrene
292638-84-7

styrene

B

tetralin
119-64-2

tetralin

C

benzocyclobutene
694-87-1

benzocyclobutene

D

cis-5-decene-3,7-diyne
122911-16-4

cis-5-decene-3,7-diyne

Conditions
ConditionsYield
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
78091-33-5

(Z)-3,4-diethylhexa-1,5-diyn-3-ene

A

tetralin
119-64-2

tetralin

B

2-ethylstyrene
7564-63-8

2-ethylstyrene

C

benzocyclobutene
694-87-1

benzocyclobutene

D

cis-5-decene-3,7-diyne
122911-16-4

cis-5-decene-3,7-diyne

Conditions
ConditionsYield
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
o-Xylylene dichloride
612-12-4

o-Xylylene dichloride

A

o-xylene
95-47-6

o-xylene

B

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
With magnesium at 600℃;A 15%
B 73%
2-methylbenzyl bromide
89-92-9

2-methylbenzyl bromide

A

o-xylene
95-47-6

o-xylene

B

benzocyclobutene
694-87-1

benzocyclobutene

C

1,2-bis(2-methylphenyl)ethane
952-80-7

1,2-bis(2-methylphenyl)ethane

D

(E)-2,2'-dimethylstilbene
36888-18-3

(E)-2,2'-dimethylstilbene

Conditions
ConditionsYield
With magnesium at 600℃; under 0.15 Torr;A n/a
B n/a
C 70%
D n/a
[2.2]Paracyclophan
1633-22-3

[2.2]Paracyclophan

A

styrene
292638-84-7

styrene

B

para-xylene
106-42-3

para-xylene

C

benzocyclobutene
694-87-1

benzocyclobutene

D

toluene
108-88-3

toluene

E

benzene
71-43-2

benzene

Conditions
ConditionsYield
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
1633-22-3

[2.2]Paracyclophan

A

styrene
292638-84-7

styrene

B

para-xylene
106-42-3

para-xylene

C

benzocyclobutene
694-87-1

benzocyclobutene

D

benzene
71-43-2

benzene

Conditions
ConditionsYield
at 930℃; Further byproducts given;A 55%
B 31%
C 4%
D 4%
1,2-bis[(phenylseleno)methyl]benzene
78808-36-3

1,2-bis[(phenylseleno)methyl]benzene

A

1,3-dihydro-2-benzoselenophene
35951-68-9

1,3-dihydro-2-benzoselenophene

B

benzocyclobutene
694-87-1

benzocyclobutene

C

anthracene
120-12-7

anthracene

D

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
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
68913-13-3

1,1-Dichlorobenzocyclobutene

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
With ammonia; lithium; isopropyl alcohol In diethyl ether at -60 - -40℃; for 6h;46%
1,2-bis[(phenylseleno)methyl]benzene
78808-36-3

1,2-bis[(phenylseleno)methyl]benzene

A

1,3-dihydro-2-benzoselenophene
35951-68-9

1,3-dihydro-2-benzoselenophene

B

benzocyclobutene
694-87-1

benzocyclobutene

C

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
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%
1-(fluoromethyl)-2-methylbenzene
62037-88-1

1-(fluoromethyl)-2-methylbenzene

A

styrene
292638-84-7

styrene

B

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
at 770℃;A 41 % Chromat.
B 30%
bis-<2-(methylthio)benzyl> oxalate
345937-14-6

bis-<2-(methylthio)benzyl> oxalate

A

2,3-dihydrobenzo(b)thiophene
4565-32-6

2,3-dihydrobenzo(b)thiophene

B

1,3-Dihydrobenzothiophen
2471-92-3

1,3-Dihydrobenzothiophen

C

benzocyclobutene
694-87-1

benzocyclobutene

D

anthracene
120-12-7

anthracene

E

methyl o-tolyl sulfide
14092-00-3

methyl o-tolyl sulfide

F

C8H9S
86509-88-8

C8H9S

Conditions
ConditionsYield
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
345937-14-6

bis-<2-(methylthio)benzyl> oxalate

A

2,3-dihydrobenzo(b)thiophene
4565-32-6

2,3-dihydrobenzo(b)thiophene

B

1,3-Dihydrobenzothiophen
2471-92-3

1,3-Dihydrobenzothiophen

C

benzocyclobutene
694-87-1

benzocyclobutene

D

methyl o-tolyl sulfide
14092-00-3

methyl o-tolyl sulfide

Conditions
ConditionsYield
at 800℃; under 0.001 Torr; for 1.66667h; Further byproducts given;A 8%
B 11%
C 29%
D n/a
2-methylphenyl acetate
533-18-6

2-methylphenyl acetate

A

styrene
292638-84-7

styrene

B

2-Ethyltoluene
611-14-3

2-Ethyltoluene

C

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
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
79430-65-2

4,5-Dihydrocycloocta-1,2,3-selenadiazol

A

2,3-Dihydrobenzoselenophene
58646-17-6

2,3-Dihydrobenzoselenophene

B

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
copper at 180℃; under 20 Torr;A 16%
B 24%
p-tolyldiazomethane
23304-24-7

p-tolyldiazomethane

A

styrene
292638-84-7

styrene

B

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
at 400℃;A 21%
B 20%
at 375℃; flash vacuum thermolysis; Yield given. Title compound not separated from byproducts;
Lithium Salt of Benzocyclobutenone Tosylhydrazone
72610-89-0

Lithium Salt of Benzocyclobutenone Tosylhydrazone

A

benzocyclobutenone
3469-06-5

benzocyclobutenone

B

o-xylene
95-47-6

o-xylene

C

2-Methylbenzonitrile
529-19-1

2-Methylbenzonitrile

D

benzocyclobutene
694-87-1

benzocyclobutene

E

cis-1-(1-benzocyclobutenylidene)benzocyclobutene
72610-88-9

cis-1-(1-benzocyclobutenylidene)benzocyclobutene

F

trans-1-(1-Benzocyclobutenylidene)benzocyclobutene
72610-87-8

trans-1-(1-Benzocyclobutenylidene)benzocyclobutene

Conditions
ConditionsYield
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
2471-91-2

1,3-dihydrobenzo[c]thiophene-2,2-dioxide

A

o-xylene
95-47-6

o-xylene

B

benzocyclobutene
694-87-1

benzocyclobutene

C

5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene
1460-59-9

5,6,11,12-tetrahydro-dibenzo[a,e]cyclooctene

Conditions
ConditionsYield
at 280℃;
1,3-dihydrobenzo[c]thiophene-2,2-dioxide
2471-91-2

1,3-dihydrobenzo[c]thiophene-2,2-dioxide

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
at 460 - 770℃; unter Stickstoff.Pyrolysis;
With chromium-promoted Raney-nickel at 460 - 770℃; Pyrolysis;
at 362℃;
1-chloro-1,2-dihydrobenzocyclobutene
61599-88-0

1-chloro-1,2-dihydrobenzocyclobutene

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
With palladium on activated charcoal Hydrogenation;
1,2-Dijod-benzocyclobutan
6639-21-0

1,2-Dijod-benzocyclobutan

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
With palladium on activated charcoal; sodium ethanolate Hydrogenation;
With lithium aluminium tetrahydride
7,8-Dibromobicyclo<4.2.0>octa-1,3,5-trien
22250-72-2

7,8-Dibromobicyclo<4.2.0>octa-1,3,5-trien

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
With lithium aluminium tetrahydride
isochromane
493-05-0

isochromane

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
at 685℃;
isochroman-3-one
4385-35-7

isochroman-3-one

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
at 570℃;
tetralin
119-64-2

tetralin

A

ethene
74-85-1

ethene

B

benzocyclobutene
694-87-1

benzocyclobutene

Conditions
ConditionsYield
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
119-64-2

tetralin

A

styrene
292638-84-7

styrene

B

1-methyl-2-(2-propenyl)-benzene
1587-04-8

1-methyl-2-(2-propenyl)-benzene

C

1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

D

benzocyclobutene
694-87-1

benzocyclobutene

E

phenylacetylene
536-74-3

phenylacetylene

F

1-indene
95-13-6

1-indene

Conditions
ConditionsYield
In gas under 0.3 Torr; Product distribution; Mechanism; Irradiation; laser-induced decomposition, multiphoton excitation, energy/pulse 0.4 J, 13020 pulses;
tetralin
119-64-2

tetralin

A

styrene
292638-84-7

styrene

B

1-methyl-2-(2-propenyl)-benzene
1587-04-8

1-methyl-2-(2-propenyl)-benzene

C

naphthalene
91-20-3

naphthalene

D

1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

E

benzocyclobutene
694-87-1

benzocyclobutene

F

1-indene
95-13-6

1-indene

Conditions
ConditionsYield
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
119-64-2

tetralin

A

styrene
292638-84-7

styrene

B

1-methyl-2-(2-propenyl)-benzene
1587-04-8

1-methyl-2-(2-propenyl)-benzene

C

1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

D

1-methyl-2-vinyl-benzene
611-15-4

1-methyl-2-vinyl-benzene

E

benzocyclobutene
694-87-1

benzocyclobutene

F

1-indene
95-13-6

1-indene

Conditions
ConditionsYield
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
119-64-2

tetralin

A

styrene
292638-84-7

styrene

B

naphthalene
91-20-3

naphthalene

C

1,2-Dihydronaphthalene
447-53-0

1,2-Dihydronaphthalene

D

benzocyclobutene
694-87-1

benzocyclobutene

E

1-indene
95-13-6

1-indene

Conditions
ConditionsYield
at 888℃; under 0.1 Torr; Product distribution; other temp.;
benzocyclobutene
694-87-1

benzocyclobutene

(9S,10S)-(-)-Dimethyl 9,10-Dihydro-9,10-ethenoanthracene-1,5-dicarboxylate
40443-30-9

(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
73353-34-1

(5S,12S)-(-)-dimethyl 5,5a,6,11,11a,12-hexahydro-5,12<1',2'>benzenonaphthacene-1,15-dicarboxylate

Conditions
ConditionsYield
In toluene at 250℃; for 16h; sealed tube;100%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

benzocyclobutene
694-87-1

benzocyclobutene

2,5-Bis(trimethylsilyl)bicyclo<4.2.0>octa-1(6),3-diene
145708-70-9

2,5-Bis(trimethylsilyl)bicyclo<4.2.0>octa-1(6),3-diene

Conditions
ConditionsYield
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)
12110-37-1

tricarbonyl(naphthalene)chromium(0)

benzocyclobutene
694-87-1

benzocyclobutene

cyclobutabenzenetricarbonylchromium(0)
99537-78-7

cyclobutabenzenetricarbonylchromium(0)

Conditions
ConditionsYield
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
694-87-1

benzocyclobutene

N-acetyl-1,3-oxazol-2-one
60759-49-1

N-acetyl-1,3-oxazol-2-one

(3aS,9aR)-3-Acetyl-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-d]oxazol-2-one
127541-96-2

(3aS,9aR)-3-Acetyl-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-d]oxazol-2-one

Conditions
ConditionsYield
In toluene at 230℃; for 48h;90%
benzocyclobutene
694-87-1

benzocyclobutene

6,7-dibromo-1,4-epoxy-1,4-dihydronaphthalene
106750-88-3

6,7-dibromo-1,4-epoxy-1,4-dihydronaphthalene

2,3-dibromo-5,5a,6,11,11a,12-hexahydronaphthacene 5,12-endoxide
110372-79-7

2,3-dibromo-5,5a,6,11,11a,12-hexahydronaphthacene 5,12-endoxide

Conditions
ConditionsYield
In toluene at 190℃; for 24h;89%
benzocyclobutene
694-87-1

benzocyclobutene

1,4-dihydro-1,4-epoxyanthracene
22187-13-9

1,4-dihydro-1,4-epoxyanthracene

5,5a,6,13,13a,14-hexahydropentacene 6,13-endoxide
110372-77-5

5,5a,6,13,13a,14-hexahydropentacene 6,13-endoxide

Conditions
ConditionsYield
In toluene at 190℃; for 24h;87%
benzocyclobutene
694-87-1

benzocyclobutene

(1α,4α,5β,8β)-1,4,5,8-tetrahydro-1,4:5,8-diepoxyanthracene
87207-46-3

(1α,4α,5β,8β)-1,4,5,8-tetrahydro-1,4:5,8-diepoxyanthracene

C30H26O2
110454-01-8

C30H26O2

Conditions
ConditionsYield
In toluene at 185 - 195℃; for 24h;87%
η6-(naphtalene)(η5-cyclopentadienyl)-iron(II) hexafluorophosphate

η6-(naphtalene)(η5-cyclopentadienyl)-iron(II) hexafluorophosphate

benzocyclobutene
694-87-1

benzocyclobutene

(η6-benzocyclobutene)(η5-cyclopentadienyl)iron(II) hexafluorophosphate
705973-92-8

(η6-benzocyclobutene)(η5-cyclopentadienyl)iron(II) hexafluorophosphate

Conditions
ConditionsYield
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
573-57-9

1,4-dihydronaphthalene-1,4-epoxide

benzocyclobutene
694-87-1

benzocyclobutene

5,5a,6,11,11a,12-hexahydronaphthacene 5,12-endoxide
110372-78-6

5,5a,6,11,11a,12-hexahydronaphthacene 5,12-endoxide

Conditions
ConditionsYield
In toluene at 190℃; for 24h;86%
benzocyclobutene
694-87-1

benzocyclobutene

(1α,4α,5α,8α)-1,4,5,8-tetrahydro-1,4:5,8-diepoxyanthracene
87248-22-4

(1α,4α,5α,8α)-1,4,5,8-tetrahydro-1,4:5,8-diepoxyanthracene

C30H26O2
110372-76-4

C30H26O2

Conditions
ConditionsYield
In toluene at 185 - 195℃; for 24h;84%
4-methylbenzotrifluoride
6140-17-6

4-methylbenzotrifluoride

benzocyclobutene
694-87-1

benzocyclobutene

bicyclo[4.2.0]octa-1,3,5-trien-3-yl 4-tolyl ketone

bicyclo[4.2.0]octa-1,3,5-trien-3-yl 4-tolyl ketone

Conditions
ConditionsYield
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
41371-94-2, 14974-11-9, 96647-88-0

tris(ammonia)chromium tricarbonyl

benzocyclobutene
694-87-1

benzocyclobutene

cyclobutabenzenetricarbonylchromium(0)
99537-78-7

cyclobutabenzenetricarbonylchromium(0)

Conditions
ConditionsYield
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%
benzocyclobutene
694-87-1

benzocyclobutene

4-bromobenzocyclobutene
1073-39-8

4-bromobenzocyclobutene

Conditions
ConditionsYield
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
20212-13-9

1,3-diacetyl-2,3-dihydro-1H-imidazol-2-one

benzocyclobutene
694-87-1

benzocyclobutene

(3aR,9aS)-1,3-Diacetyl-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-d]imidazol-2-one
127541-97-3

(3aR,9aS)-1,3-Diacetyl-1,3,3a,4,9,9a-hexahydro-naphtho[2,3-d]imidazol-2-one

Conditions
ConditionsYield
In toluene at 230℃; for 48h;74%
benzocyclobutene
694-87-1

benzocyclobutene

chromium(0) hexacarbonyl
199620-14-9, 13007-92-6

chromium(0) hexacarbonyl

cyclobutabenzenetricarbonylchromium(0)
99537-78-7

cyclobutabenzenetricarbonylchromium(0)

Conditions
ConditionsYield
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
872-36-6

vinylene carbonate

benzocyclobutene
694-87-1

benzocyclobutene

cis-1,4-dihydronaphthalene carbonate
127541-95-1

cis-1,4-dihydronaphthalene carbonate

Conditions
ConditionsYield
In toluene at 230℃; for 48h;70%
In toluene at 230℃; for 48h;70%
Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

benzocyclobutene
694-87-1

benzocyclobutene

bicyclo<4.2.0>octa-1,3,5-triene-3-carboxaldehyde
112892-88-3

bicyclo<4.2.0>octa-1,3,5-triene-3-carboxaldehyde

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 0℃; for 1h;70%
With titanium tetrachloride Formylation;34%
With titanium tetrachloride In dichloromethane at 0℃;34%
benzocyclobutene
694-87-1

benzocyclobutene

9-methoxyanthracene
2395-96-2

9-methoxyanthracene

C23H20O
117081-96-6

C23H20O

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 200℃; for 15.5h;70%
benzocyclobutene
694-87-1

benzocyclobutene

7,8-Dibromobicyclo<4.2.0>octa-1,3,5-trien
22250-72-2

7,8-Dibromobicyclo<4.2.0>octa-1,3,5-trien

Conditions
ConditionsYield
With N-Bromosuccinimide In 1,2-dichloro-ethane at 120℃; for 48h; Inert atmosphere;70%
benzene tricarbonylmolybdenum(0)
12287-81-9

benzene tricarbonylmolybdenum(0)

benzocyclobutene
694-87-1

benzocyclobutene

tricarbonyl(η6-1,2-dihydrocyclobutabenzene)molybdenum
164588-51-6

tricarbonyl(η6-1,2-dihydrocyclobutabenzene)molybdenum

Conditions
ConditionsYield
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
694-87-1

benzocyclobutene

(+/-)4-bromo-11-oxatricyclo[6.2.1.02,7]-undeca-2,4,6,9-tetraene
477907-60-1

(+/-)4-bromo-11-oxatricyclo[6.2.1.02,7]-undeca-2,4,6,9-tetraene

C18H15BrO
1350636-55-3

C18H15BrO

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 220℃; for 6h; sealed tube;64%
benzocyclobutene
694-87-1

benzocyclobutene

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

1-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)-3-chloropropan-1-one
116055-00-6

1-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)-3-chloropropan-1-one

Conditions
ConditionsYield
With aluminum (III) chloride In nitromethane at 0 - 20℃; Friedel-Crafts acylation; Inert atmosphere;63%
With aluminium trichloride; nitromethane
maleic anhydride
108-31-6

maleic anhydride

benzocyclobutene
694-87-1

benzocyclobutene

1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic acid anhydride
29811-05-0

1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic acid anhydride

Conditions
ConditionsYield
In 1,3,5-trimethyl-benzene at 210℃; for 48h; autoclave;63%

Benzocyclobutene Specification

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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