1-Bromobenzocyclobutene Chemical Properties

Boiling point:

90 °C/10.5 mmHg (lit.)

Density 

1.45 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.59(lit.)

Flash point:

205 °F

storage temp. 

Sealed in dry,Room Temperature

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C8H7Br/c9-8-5-6-3-1-2-4-7(6)8/h1-4,8H,5H2

InChIKey

JQOFZAWKFBCSHK-UHFFFAOYSA-N

SMILES

C12C(C(Br)C1)=CC=CC=2

Safety Information

WGK Germany 

3

HS Code 

2903898090

MSDS

• Language:English Provider:SigmaAldrich

1-Bromobenzocyclobutene Usage And Synthesis

Chemical Properties

Colorless to pale yellow liquid

Uses

1-Bromobenzocyclobutene may be used in the synthesis of following compounds:

• five-membered zirconacycles
• benzocyclobutenol and benzocyclobutenone
• 2,3-dimethoxyprotoberberinium bromide, via reaction with 3,4-dihydro-6,7-dimethoxyisoquinoline

General Description

1-Bromobenzocyclobutene is a useful synthon. It has important applications in organometallic methodology. Reaction between cycloheptatriene, bromoform, potassium carbonate and 18-crown-6 at 140°C yields 1-bromobenzocyclobutene.

Synthesis

In a 250 mL round bottom flask equipped with a drying tube and condenser, cycloheptatriene (30.7 g, 300 mmol), tribromomethane (25.3 g, 100 mmol), anhydrous K2CO3 (15.0 g, 109 mmol), and 18-crown-6 (0.75 g) were added. The mixture was heated with stirring at 145°C for 9-10 hours. After completion of the reaction, the solution was allowed to cool to room temperature and diluted with an equal volume of acetone. Silica gel (15.0 g) was added to the reaction mixture and the insoluble solid residue was separated by vacuum filtration and the filter cake was washed with acetone until the washings were colorless. The filtrate was concentrated and the residual cycloheptatriene was removed by distillation. The viscous brown residue was dissolved in hot petroleum ether and the filtrate was concentrated after removing the precipitate by filtration. Vacuum distillation through a Vigreaux column gave slightly impure 1-bromobenzocyclobutene. Further purification by redistillation gave pure 1-bromobenzocyclobutene (2.95 g, 5.94% yield) as a light yellow liquid.1H NMR (300 MHz, CDCl3) δ 7.28 (m, 1H, ArH), 7.16 (d, 1H, J = 7.0 Hz, ArH), 7.07 (d, 1H, J = 6.4 Hz, ArH), 7.07 (d, 1H, J = 6.4 Hz, ArH) 5.39 (m, 1H, CH), 3.85 (dd, 1H, J = 4.4 Hz, J = 14.7 Hz, CH2), 3.45 (d, 1H, J = 14.7 Hz, CH2).

References

[1] Patent: WO2008/24435, 2008, A2. Location in patent: Page/Page column 104

1-Bromobenzocyclobutene(21120-91-2)Related Product Information

• 4'-Bromopropiophenone
• 2-Bromobenzonitrile
• 3-Bromoanisole
• Benzocyclobutene
• 1,2-Dibromobenzene
• 4-Bromofluorobenzene
• 1,3-Dibromobenzene
• 1-Hydroxymethylbenzocyclobutene
• Benzocyclobutene-4-boronic acid
• Benzocyclobutyl-1-carboxylic acid
• 4-Aminobenzocyclobutene
• 4-Hydroxymethylbenzocyclobutene
• 4-Carboxaldehydebenzocyclobutene
• 4-Bromobenzocyclobutene
• ALPHA-BROMOSTYRENE
• 4-Fluorobenzyl bromide
• beta-Bromostyrene
• 1-Bromobenzocyclobutene