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Benzocyclobutene

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Name

Benzocyclobutene

EINECS N/A
CAS No. 694-87-1 Density 1.033 g/cm3
PSA 0.00000 LogP 1.78520
Solubility N/A Melting Point N/A
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 N/A
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;

Article Data 70

Benzocyclobutene Synthetic route

552-45-4

1-chloromethyl-2-methylbenzene

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;
552-45-4

1-chloromethyl-2-methylbenzene

A

292638-84-7

styrene

B

694-87-1

benzocyclobutene

Conditions
ConditionsYield
at 647℃; under 0.08 Torr;A 3%
B 77%
at 647℃;A 2 % Chromat.
B 80 % Chromat.
78091-33-5

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

A

292638-84-7

styrene

B

119-64-2

tetralin

C

694-87-1

benzocyclobutene

D

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%
78091-33-5

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

A

119-64-2

tetralin

B

7564-63-8

2-ethylstyrene

C

694-87-1

benzocyclobutene

D

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
612-12-4

o-Xylylene dichloride

A

95-47-6

o-xylene

B

694-87-1

benzocyclobutene

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

2-methylbenzyl bromide

A

95-47-6

o-xylene

B

694-87-1

benzocyclobutene

C

952-80-7

1,2-bis(2-methylphenyl)ethane

D

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
1633-22-3

[2.2]Paracyclophan

A

292638-84-7

styrene

B

106-42-3

para-xylene

C

694-87-1

benzocyclobutene

D

108-88-3

toluene

E

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;
1633-22-3

[2.2]Paracyclophan

A

292638-84-7

styrene

B

106-42-3

para-xylene

C

694-87-1

benzocyclobutene

D

71-43-2

benzene

Conditions
ConditionsYield
at 930℃; Further byproducts given;A 55%
B 31%
C 4%
D 4%
78808-36-3

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

A

35951-68-9

1,3-dihydro-2-benzoselenophene

B

694-87-1

benzocyclobutene

C

120-12-7

anthracene

D

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%
68913-13-3

1,1-Dichlorobenzocyclobutene

694-87-1

benzocyclobutene

Conditions
ConditionsYield
With ammonia; lithium; isopropyl alcohol In diethyl ether at -60 - -40℃; for 6h;46%

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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