1,1,2,2-Tetrakis(4-bromophenyl)ethene Chemical Properties

Melting point:

251-252 °C(Solv: acetone (67-64-1))

Boiling point:

575.1±45.0 °C(Predicted)

Density 

1.750±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C26H16Br4/c27-21-9-1-17(2-10-21)25(18-3-11-22(28)12-4-18)26(19-5-13-23(29)14-6-19)20-7-15-24(30)16-8-20/h1-16H

InChIKey

BIRLDGKMJJEZRI-UHFFFAOYSA-N

SMILES

C(/C1=CC=C(Br)C=C1)(\C1=CC=C(Br)C=C1)=C(\C1=CC=C(Br)C=C1)/C1=CC=C(Br)C=C1

Safety Information

HS Code 

2903.99.8001

1,1,2,2-Tetrakis(4-bromophenyl)ethene Usage And Synthesis

Application

Tetra-(4-bromophenyl)ethylene is an olefinic organic compound that can be used as an intermediate in organic synthesis.

General Description

AIE (aggregation-induced emission)-active building block.

Synthesis

[0085] 1) Synthesis of 1,1,2,2-tetrakis(4-bromophenyl)ethylene (A). 75 mmol (25 g) of 1,1,2,2-tetraphenylethylene was placed on a watch glass in a desiccator. Add 585 mmol (30 mL) of liquid bromine to the bottom of the desiccator. The desiccator was closed with a lid with small holes to allow the HBr gas generated by the reaction to escape.After 7 days, the resulting yellow solid was collected and recrystallized with dichloromethane/methanol (2:1, v/v) to give a white crystalline product. Yield: 37 g, 76% yield.1H NMR (CDCl3, 300 MHz, 298 K): δ 6.84 (d, 8H, HarH), 7.26 (d, 8H, HbrH). Impurity peak: δ 7.26 (m, CDCl3), δ 1.6 (m, H2O).

References

[1] Journal of the American Chemical Society, 2015, vol. 137, # 32, p. 10064 - 10067
[2] New Journal of Chemistry, 2016, vol. 40, # 11, p. 9415 - 9423
[3] Journal of the American Chemical Society, 2017, vol. 139, # 50, p. 18142 - 18145
[4] Chemistry - A European Journal, 2017, vol. 23, # 35, p. 8390 - 8394
[5] Chemistry - A European Journal, 2017, vol. 23, # 51, p. 12565 - 12574

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