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156028-26-1

156028-26-1 Structure

156028-26-1 Structure
IdentificationMore
[Name]

1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride
[CAS]

156028-26-1
[Synonyms]

1,6,7,12-TETRACHLOROPERYLENE TETRACARBOXYLIC ACID DIANHYDRIDE
TETRACHLOROPERYLENE TETRACARBOXYLIC ACID DIANHYDRIDE
1,6,7,12-Tetrachloro-3,4,9,10-perylene-tetracarboxylic acid dianhydride
6,7,12,13-Tetrachloro-3,4,9,10-perylene tetracarboxylic acid dianhydride
1,6,7,12-Terachloro-3,4,9,10-teraanhydrideperylene
TETRACHLOROPERYLENE TETRACARBOXYLIC ACID DIANHYDRIDE: TECH.
1,6,7,12-TETRACHLORO-3,4,9-PERYLENE TETRACARBOXYLIC ACID
[EINECS(EC#)]

937-421-2
[Molecular Formula]

C24H4Cl4O6
[MDL Number]

MFCD08056065
[Molecular Weight]

530.1
[MOL File]

156028-26-1.mol
Chemical PropertiesBack Directory
[Boiling point ]

757.1±55.0 °C(Predicted)
[density ]

1.962±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,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)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501c
Hazard InformationBack Directory
[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-Perylenetetracarboxylic dianhydride

128-69-8

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

156028-26-1

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
Spectrum DetailBack Directory
[Spectrum Detail]

1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride(156028-26-1)1HNMR
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