1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride Chemical Properties

Boiling point:

757.1±55.0 °C(Predicted)

Density 

1.962±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly, Heated)

form 

Solid

color 

Red

Stability:

Moisture Sensitive

InChI

InChI=1S/C24H4Cl4O6/c25-9-1-5-13-6(22(30)33-21(5)29)2-11(27)17-18-12(28)4-8-14-7(23(31)34-24(8)32)3-10(26)16(20(14)18)15(9)19(13)17/h1-4H

InChIKey

YGRXZLAMYLGXMF-UHFFFAOYSA-N

SMILES

C1(=O)OC(=O)C2=CC(Cl)=C3C4=C2C1=CC(Cl)=C4C1=C2C4=C(C=C1Cl)C(=O)OC(=O)C4=CC(Cl)=C32

CAS DataBase Reference

156028-26-1(CAS DataBase Reference)

1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride Usage And Synthesis

Uses

1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride is a perylene derivative used in the preparation of fluorofluorescent perylene bisimides for use in perfluorinated liquids. The fluorescence of 1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride has made it a viable target for use as fluorescent liquid crystals.

Synthesis

3,4,9,10-tetracarboxylic dianhydride (3.30 g, 8.41 mmol) was used as a raw material, mixed with chlorosulfonic acid (20 mL, 300 mmol) and iodine (0.56 g, 2.20 mmol), and the reaction was stirred for 30 hours at 65 °C. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently added slowly dropwise to an ice-water mixture. The precipitated red solid product was collected by filtration in a yield of 4.14 g in 92% yield. The product was analyzed by 1H NMR (d-DMSO, ppm) showing: 8.75 (s, 4H, aryl proton). 13C NMR (d-DMSO, ppm) analysis showed: 119.75, 125.29, 129.5, 134.88, 136.22, 158.16, 168.53. mass spectral (EI) analysis showed: m/z 532.

References

[1] Journal of the American Chemical Society, 2008, vol. 130, # 26, p. 8271 - 8279
[2] Synlett, 2018, vol. 29, # 19, p. 2509 - 2514
[3] Journal of the American Chemical Society, 2015, vol. 137, # 15, p. 5210 - 5224
[4] ACS Combinatorial Science, 2016, vol. 18, # 12, p. 723 - 739
[5] Polymer, 2014, vol. 55, # 23, p. 6058 - 6068

1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride(156028-26-1)Related Product Information

• Isopropyl chloroformate
• 3-Chloroperoxybenzoic acid
• 4-(Chloromethyl)benzoic acid
• 3,3',4,4'-Biphenyltetracarboxylic dianhydride
• 2-Sulfobenzoic anhydride
• Benzoic anhydride
• Benzyl chloroformate
• Methyl chloroformate
• Ethyl chloroformate
• 1-CHLOROANTHRACENE
• Perylene
• 3,4,9,10-Perylenetetracarboxylic dianhydride
• 2-ANTHRACENECARBOXYLIC ACID
• 2,7-dichloronaphthalene
• ANTHRACENE-2,6-DICARBOXYLIC ACID
• 2-HYDROXYMETHYLPHENANTHRENE
• 3,9-perylenedicarboxylic acid
• 1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride