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4-Bromobenzocyclobutene

4-Bromobenzocyclobutene structure

CAS No:
1073-39-8
Formula:
C8H7Br
Chemical Name:
4-Bromobenzocyclobutene
Categories:
Organic Chemistry > Hydrocarbons and Derivatives

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Description

colorless or light yellow liquid

4-Bromobenzocyclobutene Basic Attributes

Molecular Weight：

183.05

Exact Mass：

181.973099

HScode：

2903890090

Characteristics

PSA：

XLogP3：

2.2

Density：

1.470 g/mL at 25 °C

Melting Point：

94-97 °C(lit.)

Boiling Point：

118-119 °C(Press: 20 Torr)

Flash Point：

100℃

Refractive Index：

n20/D1.589

Safety Information

wgk germany：

hazard class code：

R36/37/38:Irritating to eyes, respiratory system and skin .

safety instructions：

S26-S36

Marks：

4-Bromobenzocyclobutene Use and Manufacturing

The synthesis of a tetracene brominated in the 2-position is shown by way of example in the following illustration: In a first step, α-chloro-o-xylene 1 was subjected to pyrolysis at approximately 800° C. and 0.5 mbar. Benzocyclobutene 2 was obtained in a 45percent yield. The selective bromination thereof was carried out by treating benzocyclobutene, dissolved in acetic acid, with a mixture of bromine and iodine at room temperature, resulting in 4-bromobenzocyclobutene 3. Dissolving in toluene and heating with a slight molar excess of 1, 4-dihydro-1, 4-epoxynaphthalene 4 at 220° C. for 20 hours resulted in an 80percent yield of a pure endo/exo mixture of the Diels-Alder addition product 5, a colorless crystalline material. This material was heated at reflux in acetic anhydride in the presence of concentrated hydrochloric acid, thus forming 9-bromo-6, 11-dihydrotetracene 6. The Yamamoto coupling then resulted in 2-(5, 12-dihydrotetracene-2-yl)-5, 12-dihydrotetracene 7. The coupling reaction was carried out in an approximately 80percent yield in a mixture of dimethylformamide and toluene at 80° C., using bis(cyclooctadienyl) nickel(0) in stoichiometric quantities. After recrystallization from o-dichlorobenzene, compound 7 was dehydrogenated by treatment with 2, 3-dichloro-5, 6-dicyano-p-benzoquinone (DDQ) in boiling o-xylene. After purification by repeated vacuum sublimation, orange-red crystals of 2-(tetracene-2-yl) tetracene 8 were obtained in a yield of 75percent. All intermediate products were characterized by

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