ChemicalBook--->CAS DataBase List--->156682-52-9

156682-52-9

156682-52-9 Structure

156682-52-9 Structure
IdentificationBack Directory
[Name]

1,4-DIBROMO-2,3-DIFLUOROBENZENE
[CAS]

156682-52-9
[Synonyms]

EA225
4-DIBROMO-2
2,3-Difluoro-1,4-dibromobenzene
Benzene,1,4-dibroMo-2,3-difluoro-
1,4-Dibromo-2,3-difluorobenzene 97%
1,4-Dibromo-2,3-difluorobenzene 95+%
[EINECS(EC#)]

811-056-8
[Molecular Formula]

C6H2Br2F2
[MDL Number]

MFCD09835192
[MOL File]

156682-52-9.mol
[Molecular Weight]

271.9
Chemical PropertiesBack Directory
[Boiling point ]

212℃
[density ]

2.087
[refractive index ]

1.5620-1.5660
[Fp ]

82℃
[storage temp. ]

0-10°C
[form ]

clear liquid
[color ]

Colorless to Red to Green
[InChI]

InChI=1S/C6H2Br2F2/c7-3-1-2-4(8)6(10)5(3)9/h1-2H
[InChIKey]

RGXGEFSBDPGCEU-UHFFFAOYSA-N
[SMILES]

C1(Br)=CC=C(Br)C(F)=C1F
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H227-H315-H319
[Precautionary statements ]

P210-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P403+P235-P501
[HS Code ]

2903998090
Hazard InformationBack Directory
[Uses]

1,4-Dibromo-2,3-difluorobenzene is a halogenated benzene used in the preparation of various biologically active compounds such as non-nucleoside reverse transcriptase inhibitors. 1,4-Dibromo-2,3-diflu orobenzene is also used in the synthesis of conjugated polymers for organic photovoltaics.
[Synthesis]

(2,3-difluoro-1,4-phenylene)bis(triMethylsilane)

867366-94-7

1,4-DIBROMO-2,3-DIFLUOROBENZENE

156682-52-9

1,4-Dibromo-2,3-difluorobenzene (5) was synthesized as follows: bromine (9.9 mL) was added to a 100 mL two-necked round-bottomed flask, which was connected to a condenser tube and a drying tube under ice bath conditions. Subsequently, 2,3-difluoro-1,4-bis(trimethylmethylsilyl)benzene (4.5 g, 19.34 mmol) was added, and the mixture was stirred at 58 °C for 1 hour. Next, another portion of bromine (0.5 mL) was added to the mixture and stirring was continued at the same temperature for 12 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and the reaction was quenched by addition of sodium bicarbonate solution. The mixture was extracted with ethyl acetate and the organic phase was washed with brine and dried with magnesium sulfate. Subsequently, the solution was concentrated under vacuum using a rotary evaporator and the crude product was purified by column chromatography. The yield of the final product was 70%.

[References]

[1] Polymer, 2017, vol. 109, p. 115 - 125
[2] Journal of the American Chemical Society, 2015, vol. 137, # 32, p. 10420 - 10429
[3] Polymer, 2014, vol. 55, # 7, p. 1707 - 1715
[4] Patent: US2008/249151, 2008, A1. Location in patent: Page/Page column 16; 22-23
[5] Patent: US2006/25462, 2006, A1. Location in patent: Page/Page column 11; 20
Spectrum DetailBack Directory
[Spectrum Detail]

1,4-DIBROMO-2,3-DIFLUOROBENZENE(156682-52-9)1HNMR
1,4-DIBROMO-2,3-DIFLUOROBENZENE(156682-52-9)FT-IR
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