1,4-DIBROMO-2,5-DIIODOBENZENE Struktur

1,4-DIBROMO-2,5-DIIODOBENZENE

Bezeichnung:1,4-DIBROMO-2,5-DIIODOBENZENE

CAS-Nr63262-06-6

Englisch Name:1,4-DIBROMO-2,5-DIIODOBENZENE

CBNumberCB7460245

SummenformelC6H2Br2I2

Molgewicht487.7

MOL-Datei63262-06-6.mol

1,4-DIBROMO-2,5-DIIODOBENZENE physikalisch-chemischer Eigenschaften

Schmelzpunkt	163-165℃
Siedepunkt	377.2±42.0 °C(Predicted)
Dichte	2.938
storage temp.	2-8°C(protect from light)
Löslichkeit	soluble in Toluene
Aggregatzustand	powder to crystal
Farbe	White to Almost white
Sensitive	Light Sensitive
InChI	InChI=1S/C6H2Br2I2/c7-3-1-5(9)4(8)2-6(3)10/h1-2H
InChIKey	IVKPEQAIHJWGGT-UHFFFAOYSA-N
SMILES	C1(Br)=CC(I)=C(Br)C=C1I

Sicherheit

Kennzeichnung gefährlicher	Xi
HS Code	2903998090

Gefahreninformationscode (GHS)

1,4-DIBROMO-2,5-DIIODOBENZENE Chemische Eigenschaften,Einsatz,Produktion Methoden

Verwenden
1,4-Dibromo-2,5-diiodobenzene is a useful synthetic intermediate in the synthesis of Benzo[1,2-b:4,5-b'']dithiophene (B200100); a reagent in the synthesis of high-crystalline medium-band-gap polymers used for organic photovoltaic cells. Benzo[1,2-b:4,5-b'']dithiophene is also a precursor in the preparation of benzodithiophene derivatives which are useful as hole injection material, hole transport material, or fluorescent material in organic electroluminescence devices.
Synthese

106-37-6

63262-06-6

General procedure for the synthesis of 1,4-dibromo-2,5-diiodobenzene from 1,4-dibromobenzene: In a three-necked flask equipped with a 1-liter mechanical stirrer, 16.7 g (73.0 mmol) of periodic acid and 525 ml of sulfuric acid were added. After the periodate was completely dissolved, 36.4 g (219 mmol) of potassium iodide was added in batches. The reaction mixture was cooled to -30°C, followed by the slow addition of 34.5 g (146 mmol) of 1,4-dibromobenzene over 5 min. The resulting mixture was stirred continuously at -25°C for 36 hours. Upon completion of the reaction, the mixture was poured into 2 Kg of ice and the solid product was collected by filtration. The solid was dissolved in chloroform and the organic phase was washed sequentially with 5% aqueous sodium hydroxide and deionized water, then dried with anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was recrystallized by chloroform to give 36.0 g of white crystals (50% yield).1H NMR (CDCl3, 21 °C): δ = 8.02 (s, 2H). The 1H NMR spectrum was consistent with the data reported in the literature for 1,4-dibromo-2,5-diiodobenzene, confirming the successful synthesis of the target product.
Einzelnachweise
[1] Organic Letters, 2009, vol. 11, # 20, p. 4656 - 4659
[2] Journal of Organic Chemistry, 2003, vol. 68, # 23, p. 8750 - 8766
[3] Journal of the American Chemical Society, 2011, vol. 133, # 10, p. 3284 - 3287
[4] Patent: CN106543216, 2017, A. Location in patent: Paragraph 0023; 0024; 0036; 0043
[5] Patent: CN108117563, 2018, A. Location in patent: Paragraph 0028; 0029; 0030

1,4-DIBROMO-2,5-DIIODOBENZENE Upstream-Materialien And Downstream Produkte

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