| Identification | Back Directory | [Name]
HONGHUI-MED 480010000000 | [CAS]
118129-60-5 | [Synonyms]
M8390
HONGHUI-MED 480010000000
1,7-Dibromo-3,4,9,10-Tetracarboxylic Acid Dianhydride
1,7-DibroMo-3,4,9,10-perylenetetracarboxylic dianhydride
1,7-Dibromo-3,4,9,10-perylenetetracarboxylic Dianhydride >
1,7-dibromo-3,4:9,10-perylenetetracarboxylic acid dianhydride
Perylo[3,4-cd:9,10-c,d]dipyran-1,3,8,10-tetrone, 5,12-dibromo-
1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride
5,12-Dibromoanthra[2,1,9-def:6,5,10-d'e'f']-diisochromene-1,3,8,10-tetraone
5,12-DIBROMOISOCHROMENO[4',5',6':6,5,10]ANTHRA[2,1,9-DEF]ISOCHROMENE-1,3,8,10-TETRONE | [Molecular Formula]
C24H6Br2O6 | [MDL Number]
MFCD11870875 | [MOL File]
118129-60-5.mol | [Molecular Weight]
550.113 |
| Chemical Properties | Back Directory | [Melting point ]
360°C(lit.) | [Boiling point ]
840.2±65.0 °C(Predicted) | [density ]
2.159±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
powder | [color ]
Orange to Brown to Dark red | [λmax]
524nm(DMSO)(lit.) | [InChI]
InChI=1S/C24H6Br2O6/c25-13-5-12-16-10(22(28)32-24(12)30)4-2-8-18-14(26)6-11-15-9(21(27)31-23(11)29)3-1-7(19(15)18)17(13)20(8)16/h1-6H | [InChIKey]
WPBVUAVIGWNDGT-UHFFFAOYSA-N | [SMILES]
C1(=O)OC(=O)C2=CC(Br)=C3C4=C2C1=CC=C4C1=C2C4=C(C=C1Br)C(=O)OC(=O)C4=CC=C32 |
| Hazard Information | Back Directory | [Uses]
Synthetic building block of high-mobility air-stable n-type semiconductors (electron-transport small organic molecules and polymers). | [Synthesis]
Example 1: 292.5 g (0.75 mol) of 3,4,9,10-tetracarboxylic dianhydride of >98% purity was stirred with 4420 g of 100% by weight sulfuric acid for 12 hours at room temperature. Subsequently 7 g of iodine was added and the mixture was heated to 85°C. 262.5 g (1.64 mol) of bromine was added slowly and dropwise over 8 hours. Upon completion of the reaction, the mixture was cooled to room temperature and purged with nitrogen to remove excess bromine. Next, the sulfuric acid concentration was diluted to 86 wt% by adding a total of 670 g of water in batches over a period of 1 hour. During this process, the reaction mixture was again heated to 85°C. After cooling, the precipitated product was filtered through a G4 glass filter and washed with 3 kg of 86 wt% sulfuric acid. The product was stirred in 5 liters of water and then filtered again, washed to neutrality and dried under reduced pressure at 120°C. 370 g of 1,7-dibromo-3,4,9,10-perylenetetracarboxylic acid dianhydride in the form of a bright red fine crystalline powder was finally obtained, with a melting point >360 °C, a purity of >98% and a yield of 90%. Analytical data: Elemental analysis (calculated value/measured value, wt%): C: 52.4/52.1; H: 1.1/1.1; O: 17.45/17.4; Br: 29.1/29.4. IR (KBr): ν=1782+1770 (strong, C=O), 1735+1723 (strong, C=O) cm^-1; UV/VIS ( H2SO4): λmax (ε) = 408 (10309), 520 (29410), 554 (43141) nm. | [References]
[1] Angewandte Chemie - International Edition, 1998, vol. 37, # 10, p. 1434 - 1437
[2] Journal of Materials Chemistry, 2010, vol. 20, # 12, p. 2362 - 2368
[3] Asian Journal of Chemistry, 2010, vol. 22, # 9, p. 7135 - 7144
[4] Patent: US6063181, 2000, A
[5] Patent: US6143905, 2000, A |
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