4,4'-Dibromo-2,2'-diiodobiphenyl Chemical Properties

Melting point:

91℃

Boiling point:

477.6±45.0 °C(Predicted)

Density 

2.438

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Yellow

InChI

InChI=1S/C12H6Br2I2/c13-7-1-3-9(11(15)5-7)10-4-2-8(14)6-12(10)16/h1-6H

InChIKey

JPXBIAWPJOGFCF-UHFFFAOYSA-N

SMILES

C1(C2=CC=C(Br)C=C2I)=CC=C(Br)C=C1I

Safety Information

HS Code 

2903.99.8001

4,4'-Dibromo-2,2'-diiodobiphenyl Usage And Synthesis

Uses

4,4''-Dibromo-2,2’-diiodobiphenyl (CAS# 852138-89-7) is a useful building block, and is seen in the preparation of hybrid organic/inorganic heterofluorene polymers and in low band-gap polymers for use in photovoltaics.

Synthesis

Synthesis of 4,4'-Dibromo-2,2'-diiodobiphenyl A solution of diamine (16.0 g, 46.8 mmol) and concentrated HCl (56.0 mL) in water (64.0 mL) was cooled to 0 C. Next, 8.0g (116 mmol) of NaNO2 in 40 mL of water was added dropwise to the diamine solution over a period of 30 min, keeping the temperature at 0 C. After the addition of NaNO2 was complete, the resulting mixture was stirred for an additional 30 min. and an aqueous solution of KI (77.7 g in 150 mL of water) at-5 C was added dropwise over 30 min. The reaction mixture was then stirred (by mechanical stirrer) for 1h at r.t and 3 h at 60 C, giving a dark brown solution. The solution was then cooled to 25 C and the brown precipitate was collected by filtration. The crude brown solid was then purified by column chromatography (silica gel, hexane). The title compound as a white solid (7.4 g, 28 % yield). 1H NMR (CDCl3): | (ppm) 7.04 (2H, d), 7.57 (2H, d), 8.11 (2H, s).

References

[1] Journal of Materials Chemistry, 2011, vol. 21, # 32, p. 11800 - 11814
[2] Journal of Materials Chemistry A, 2016, vol. 4, # 22, p. 8750 - 8754
[3] Chemistry - An Asian Journal, 2015, vol. 10, # 10, p. 2134 - 2138
[4] Journal of the American Chemical Society, 2005, vol. 127, # 21, p. 7662 - 7663
[5] Organic Electronics: physics, materials, applications, 2018, vol. 59, p. 77 - 83

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