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Chemical Structure| 128-69-8
Chemical Structure| 128-69-8
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Product Details of [ 128-69-8 ]

CAS No. :128-69-8 MDL No. :MFCD00006916
Formula : C24H8O6 Boiling Point : -
Linear Structure Formula :C20H8(CO)4O2 InChI Key :CLYVDMAATCIVBF-UHFFFAOYSA-N
M.W : 392.32 Pubchem ID :67191
Synonyms :
Chemical Name :Anthra[2,1,9-def:6,5,10-d'e'f']diisochromene-1,3,8,10-tetraone

Calculated chemistry of [ 128-69-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 30
Num. arom. heavy atoms : 20
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 107.14
TPSA : 86.74 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 4.49
Log Po/w (WLOGP) : 4.36
Log Po/w (MLOGP) : 4.56
Log Po/w (SILICOS-IT) : 5.43
Consensus Log Po/w : 4.13

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.59
Solubility : 0.000998 mg/ml ; 0.00000254 mol/l
Class : Moderately soluble
Log S (Ali) : -6.03
Solubility : 0.000364 mg/ml ; 0.000000929 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.32
Solubility : 0.00000186 mg/ml ; 0.0000000047 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 4.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.56

Safety of [ 128-69-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 128-69-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 128-69-8 ]
  • Downstream synthetic route of [ 128-69-8 ]

[ 128-69-8 ] Synthesis Path-Upstream   1~33

  • 1
  • [ 81-33-4 ]
  • [ 128-69-8 ]
Reference: [1] Patent: CN106752059, 2017, A, . Location in patent: Paragraph 0026; 0034; 0035; 0036; 0042; 0046
[2] Patent: CN106749304, 2017, A, . Location in patent: Paragraph 0015-0032
  • 2
  • [ 110590-84-6 ]
  • [ 130296-37-6 ]
  • [ 128-69-8 ]
Reference: [1] Liebigs Annalen, 1995, # 3, p. 481 - 486
[2] Journal of the American Chemical Society, 2003, vol. 125, # 41, p. 12649 - 12654
  • 3
  • [ 139260-31-4 ]
  • [ 128-69-8 ]
  • [ 162109-59-3 ]
Reference: [1] Liebigs Annalen, 1995, # 3, p. 481 - 486
  • 4
  • [ 130296-48-9 ]
  • [ 130296-39-8 ]
  • [ 128-69-8 ]
Reference: [1] Liebigs Annalen, 1995, # 3, p. 481 - 486
  • 5
  • [ 81-32-3 ]
  • [ 128-69-8 ]
Reference: [1] Monatshefte fuer Chemie, 1928, vol. 50, p. 92
[2] Monatshefte fuer Chemie, 1928, vol. 50, p. 92
[3] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 9, p. 2705 - 2708
  • 6
  • [ 110590-81-3 ]
  • [ 128-69-8 ]
  • [ 522647-62-7 ]
Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 12, p. 3330 - 3345
  • 7
  • [ 7783-06-4 ]
  • [ 128-69-8 ]
Reference: [1] Dalton Transactions, 2014, vol. 43, # 30, p. 11542 - 11547
  • 8
  • [ 5521-31-3 ]
  • [ 70654-96-5 ]
  • [ 128-69-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 4, p. 1269 - 1270
  • 9
  • [ 52000-75-6 ]
  • [ 70654-99-8 ]
  • [ 128-69-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 4, p. 1269 - 1270
  • 10
  • [ 59385-83-0 ]
  • [ 70654-97-6 ]
  • [ 128-69-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 4, p. 1269 - 1270
  • 11
  • [ 59442-38-5 ]
  • [ 70654-98-7 ]
  • [ 128-69-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 4, p. 1269 - 1270
  • 12
  • [ 82718-41-0 ]
  • [ 82718-41-0 ]
  • [ 128-69-8 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 887 - 894[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 5, p. 1024 - 1033
  • 13
  • [ 38687-17-1 ]
  • [ 128-69-8 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 887 - 894[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 5, p. 1024 - 1033
  • 14
  • [ 78-83-1 ]
  • [ 128-69-8 ]
  • [ 2744-50-5 ]
Reference: [1] Patent: CN103773080, 2016, B, . Location in patent: Paragraph 0015; 0016; 0021-0025
  • 15
  • [ 128-69-8 ]
  • [ 118129-60-5 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: at 20℃; for 2 h;
Stage #2: at 80 - 100℃; for 4 - 6 h;
EXAMPLE 1; 1,7-dibromoperylene-3,4,9,10-tetracarboxyl dianhydride (2)(2) The 3,4,9, 10-perylenetetracarboxyl dianhydride (1) is dissolved in96percent H2SO4 and left under stirring for 2 hours at room temperature. Then, iodine (30-40 mmoles per mole of anhydride) is added and the composition is heated to 8O0C. When the purple vapours of iodine are given off, the bromide is added drop by drop (molar ratio with the anhydride 2-2.5:1) and the temperature is increased to about 100°C. After 4-6 hours, the reaction is extinguished by adding ice until cooling. The resulting precipitate is then filtered on Buchner filter and washed first in a 5percent solution of sodium metabisulfite to eliminate the residual bromine and then several times in water. The precipitate <n="21"/>is then dried first in an oven and then on a thimble for drying from solid form. A red solid is thus obtained, having a sufficient degree of purity to be used as such in the subsequent preparations.One of the preparations is reported below: 5 g 3,4,9, 10-perylenetetracarboxyl dianhydride (1)1.65 cc Br2 113 mg I2 100 cc 96percent H2SO46 g of 1 ,7-dibromoperylene-3,4,9,10-tetracarboxyl dianhydride (2) was obtained. The yield was 87percent.Note. Besides the 1 ,7 dibromurated isomer, the reaction also yields a small percentage of 1 ,6 disubstituted product, as can be seen from a careful examination of the 1H NMR spectra (see further on, for the complete characterisation). There is no way of separating the two isomers, neither here nor in the next steps. In the characterisations of the products obtained in the next synthesis steps, reference will exclusively be made - when not indicated otherwise - to the 1 ,7 isomer.Empirical formula: C24H6Br2Oe Molecular weight: 550 Solubility: in concentrated H2SO4 Elemental analysis:Theoretical data Experimental datapercent C = 52.36 percent C = 51.61percent H = 1.09 percent H = 1.081H NMR spectrum, 300 MHz: solvent D2SO4 The spectrum is composed of three signals present in the aromatic area: δ 10.71(d 2H J=8 Hz), 10.04(s 2H), 9.82(d 2H J=8 Hz). Some lower signals are also often present, with chemical shifts very close to the ones described above: in all likelihood, these signals are to be attributed to the small percentage of 1 ,6 isomer that is formed together with the main product.
Reference: [1] Patent: WO2008/126123, 2008, A2, . Location in patent: Page/Page column 15; 19-20
[2] Tetrahedron Letters, 2004, vol. 45, # 49, p. 9015 - 9020
[3] Journal of Organic Chemistry, 2006, vol. 71, # 5, p. 2107 - 2114
[4] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 4, p. 1848 - 1858
[5] Tetrahedron, 2007, vol. 63, # 33, p. 7858 - 7865
[6] Journal of the American Chemical Society, 2009, vol. 131, # 2, p. 833 - 843
[7] Journal of Materials Chemistry, 2009, vol. 19, # 37, p. 6688 - 6698
[8] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1794 - 1799
[9] Journal of Physical Chemistry A, 2011, vol. 115, # 9, p. 1579 - 1592
[10] New Journal of Chemistry, 2010, vol. 34, # 11, p. 2537 - 2545
[11] European Journal of Organic Chemistry, 2011, # 24, p. 4564 - 4570
[12] European Journal of Organic Chemistry, 2011, # 30, p. 5955 - 5958
[13] Chemistry of Materials, 2011, vol. 23, # 3, p. 778 - 788
[14] Journal of Physical Organic Chemistry, 2011, vol. 24, # 8, p. 621 - 629
[15] Journal of Materials Chemistry, 2012, vol. 22, # 15, p. 7387 - 7394
[16] Bioconjugate Chemistry, 2011, vol. 22, # 7, p. 1309 - 1319
[17] Patent: WO2014/57511, 2014, A1, . Location in patent: Page/Page column 31
[18] Dyes and Pigments, 2013, vol. 99, # 2, p. 456 - 464
[19] RSC Advances, 2014, vol. 4, # 62, p. 32866 - 32875
[20] Journal of the Chinese Chemical Society, 2015, vol. 62, # 3, p. 280 - 286
[21] Journal of the American Chemical Society, 2016, vol. 138, # 6, p. 1792 - 1795
[22] Journal of Fluorescence, 2017, vol. 27, # 2, p. 491 - 500
[23] Chemistry - An Asian Journal, 2017, vol. 12, # 8, p. 890 - 899
[24] Journal of Photochemistry and Photobiology A: Chemistry, 2018, vol. 360, p. 270 - 277
  • 16
  • [ 128-69-8 ]
  • [ 118129-60-5 ]
YieldReaction ConditionsOperation in experiment
90% With sulfuric acid; bromine; iodine In water Example 1
A mixture of 292.5 g (0.75 mol) of perylene-3,4,9,10-tetracarboxylic dianhydride (purity>98percent) and 4420 g of 100percent by weight sulfuric acid was stirred for 12 hours at room temperature, 7 g of iodine were then added, and it was heated to 85° C. Subsequently, 262.5 g (1.64 mol) of bromine were added dropwise over 8 hours.
The reaction mixture was cooled to room temperature, the excess bromine was displaced by nitrogen and then the concentration of sulfuric acid was reduced to 86percent by weight by adding a total of 670 g of water, a little at a time, over 1 hour.
During this addition the reaction mixture heats up to 85° C. again:
it was cooled and the precipitated product was filtered off over a G4 glass frit, washed with 3 kg of 86percent by weight sulfuric acid and then stirred up in 5 l of water; the mixture was filtered again and the product was washed to neutrality and dried under reduced pressure at 120° C.
370 g of II were obtained in the form of a bright red finely crystalline powder with a melting point>360° C. and a purity of >98percent, corresponding to a yield of 90percent.
Analytical data:
Elemental analysis (percent by weight calc./found): 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 (s, C=O), 1735+1723 (s, C=O) cm-1; UV/VIS (H2 SO4): λmax (ε)=408 (10309), 520 (29410), 554 (43141) nm.
90% With sulfuric acid; bromine; iodine In water Example 1
A mixture of 292.5 g (0.75 mol) of perylene-3,4,9,10-tetracarboxylic dianhydride (purity >98percent) and 4420 g of 100percent by weight sulfuric acid was stirred for 12 hours at room temperature, 7 g of iodine were added, and the mixture was then heated to 85° C. 262.5 g (1.64 mol) of bromine were then added dropwise over 8 hours.
The reaction mixture was cooled to room temperature, the excess bromine was displaced by nitrogen, and the concentration of sulfuric acid in the reaction mixture was reduced to 86percent by weight by adding, a little at a time, a total of 670 g of water over 1 hour.
The reaction mixture, which heats up to 85° C. during this procedure, was cooled to room temperature and the precipitated product was filtered off over a G4 glass frit, washed with 3 kg of 85percent by weight sulfuric acid, then stirred up in 5 l of water, filtered off again, washed to neutrality and dried under reduced pressure at 120° C.
370 g of II were obtained in the form of a bright red, finely crystalline powder with a melting point >360° C. and a purity of >98percent, corresponding to a yield of 90percent.
81%
Stage #1: at 55℃; for 24 h;
Stage #2: at 55℃; for 5 h;
Stage #3: at 85℃; for 25 h;
In the first step a synthesis of 1 ,7-dibromoperylene-3,4:9,10-tetracarboxydianhydride represented by the general structural formula 30 was carried out: <n="35"/>1 (30)For this purpose 3,4:9,10-perylenetetracarboxylic dianhydride (28.52 g, 72.7 mmol) was added to 420 ml concentrated sulfuric acid and stirred at 55° C for 24 hours. Iodine (0.685 g, 2.70 mmol) was added to the reaction mixture and stirred for additional 5 hours, at 55° C. Bromine (8.3 ml, 162 mmol) was added dropwise to the reaction flask over 1 hour and stirred for 24 hours at 85° C. The excess bromine was then displaced with the nitrogen gas N2. Water (66 ml) was added dropwise to the cooled mixture and the precipitate was filtered off. The crude product was washed with 220 ml 86 percent H2SO4 followed by water and this procedure was repeated two times to produce the crude product (32.32 g, 81 percent). This product was used further without any purification. M.S.: 549.0 (calcd. 550.11 ).
81%
Stage #1: at 55℃; for 24 h;
Stage #2: at 55℃; for 5 h;
Stage #3: at 85℃; for 24 h; Inert atmosphere
For this purpose 3,4:9,10-perylenetetracarboxylic dianhydride (28.52 g, 72.7 mmol) was added to 420 ml concentrated sulfuric acid and stirred at 55° C for 24 hours. Iodine (0.685 g, 2.70 mmol) was added to the reaction mixture and stirred for additional 5 hours, at 55° C. Bromine (8.3 ml, 162 mmol) was added drop wise to the reaction flask over 1 hour and stirred for 24 hours at 85° C. The excess bromine was then displaced with the nitrogen gas N2. Water (66 ml) was added dropwise to the cooled mixture and the precipitate was filtered off. The crude product was washed with 220 ml 86 percent H2SO4 followed by water and this procedure was repeated two times to produce the crude product (32.32 g, 81 percent). This product was used further without any purification. M. S. : 549.0 (calcd. 550.11).
80%
Stage #1: at 55℃; for 30 h;
Stage #2: at 85℃; for 32.5 h;
Into a 1000 mL four-necked flask equipped with an exhaust gas absorber, 450 mL of concentrated sulfuric acid and perylene anhydride (29 g, 74.0 mmol) were added,Heated to 55 ° C,Heat stirring 30h,JoinI2(0.7 g),The temperature was raised to 85 ° C,Bromine (8.2 mL,162.8 mmol) of sulfuric acid was added over 2.5 hours. Canada completed, insulation reaction 30h. After cooling to room temperature, water (100 mL) was added dropwise and the solid was precipitatedOut, sand core funnel filter. Filter cake with 80percent H2SO4 (250mL) washing, and then washed to the filtrate was neutral, dry, freshRed solid of the compound of formula IVa (32.4 g) in 80percent yield
64% at 85℃; Commercially available Perylene-3,4.9,10-tetracarboxylιc dianhydπde (100.0 g, 0.255 mol) was brominated with mixture of bromine (29 rmL) and Iodine (2.38 g) in 100percent sulfuric acid (845 mL) at.~ 85° C The yield of 1 ,7-dibromoperylene-3,4-9,10-tetracarboxylic dianhydride was 90 g (64percent)Analysis: calculated' C24H6Br2O6, C 52.40, H 1.10, Br 29 05, O 17.45 percent; found: C 52 29, H, 1.07, Br 28, 79 percent. Absorption spectrum (9.82x105 M solution in 93percent sulfuric acid)- 405 (9572), 516 (27892), 553 (37769).N.N'-Dicyclohexyl-i y-dibromopeiylene-SAψ.IO-tetracarboxydiimide was synthesized by reaction of 1 ,7-dιbromoperylene-3,4.9,10-tetracarboxylιc dianhydride (30.0 g) with cyclohexylamine (18.6 mL) in N-methylpyrrolidone (390 mL) at -85 ° C. The yield of N,N'-dιcyclohexyl-1 ,7- dibromoperylene-3,4:9,10-tetracarboxydiimide was 30 g (77percent).N.N'-Dicyclohexyl-I J-di^ct-i-ynyOperylene-S^ ψ.IO-tetracarboxydiimide by Sonogashira reaction: N.N'-dicyclohexyl-I J-dibromperylene-S^ ψ.IO-tetracarboxydiimide (24.7 g) and octyne-1 (15 2 g) in the presence of bis(triphenylphosphine)palladium(ll) chloride (2.42 g), triphenylphospine (0 9 g),and copper(l) iodide (0.66 g). The yield of N.N'-dicyclohexyl-i y-dKoct-i-ynyOperylene-SAψ.IO- tetracarboxydiimide was 15.7 g (60 percent).N,N'-Dicyclohexyl-5,11-dιhexylcoronene-2,3:8,9-tetracarboxydiimιde was synthesized by heating of N,N'-dicyclohexyl-1 ,7-dι(oct-1-ynyl)perylene-3,4.9,10-tetracarboxydιιmide (7.7 g) in toluene (400 mL) in the presence of 1 ,8-Diazabicyclo[5 4.0]undec-7-ene (0 6 ml) at 100-110° C for 20 hours.5,1 i-dihexylcoronene^S'δ.ψ-tetracarboxylic dianhydride was prepared by hydrolysis of N1N'- dicyclohexyl-5,11-dihexylcoronene-2,3:8,9-tetracarboxydiimide (6 4 g, 8 3 mmol) with Potassium <n="14"/>~ ~ hydroxide (7.0 g, 85percent) in the mixture of tert-butanol (400 mL) and water (0.4 mL) at 85-900C. The yield of 5,1 i-dihexylcoronene^.S.δ.ψ-tetracarboxyhc dianhydπde was 4.2 g (83percent).N,N'-(1-undecyl)dodecyl-5,11-dιhexylcoronene-2,3:8,9-tetracarboxydiimιde by the reaction of 5,11-di(hexyl)coronene-2,3:8,9-tetracarboxylic dianhydride with 12-tricosanamine5,11-di(hexyl)coronene-2,3l8,9-tetracarboxylic dianhydride (3 44 g), 12-tricosanamine (7.38 g), benzoic acid (45 mg) and 3-chlorophenol (15 mL) was evacuated and saturated with argon two times at room temperature and 2 times at 1000C The reaction mixture was agitated at ~140°C for 1 hour and 160-165°C for 20 hours in a flow of argon. After that the reaction mixture was agitated at ~100°C and was vacuumed at 10 mm Hg for half an hour. Then apparatus was filled with argon once again and heating was continued for the next 24 hours.A drop of reaction mixture was mixed with acetic acid (5 mL), centrifuged, solid was dissolved in chloroform (0 5 mL) which was washed with water and dried over sodium sulfate. Thin layer chromatography probe showed good formation of product with Rf 0 9 (eluent: Chloroform-Hexane- Ethylacetate-Methanol (100 50:0 3:0 1 by V)).The reaction mixture was added in small portions to acetic acid (500 mL) with simultaneous shaking. The orange-red suspension was kept for 3 hours with periodic shaking, then filtered off. The filter cake was washed with water (0.5 L), and then was shaken with water (0.5 L) and chloroform (250 mL) in a separator funnel. The organic layer was separated, washed with water (2x350 mL) and dried over sodium sulfate overnight. The evaporation resulted in 7.0 g of crude product.Column chromatography was carried out using exactly tuned eluent mixture1 chloroform (700 mL), petroleum ether (2 L), ethylacetate (0 6 mL) and methanol (0 2).Column chromatography was carried out using column1 I = 20, d = 7 cm Elution of orange fraction and evaporation resulted in orange soft solid material, which was dissolved in chloroform (25 mL) and added slowly to methanol (400 mL) with agitation. The soft precipitate was dried on air overnight, then in vacuum (15 mm Hg) at mild heating (35°) for 5 hours. The yield of preparation of N1N'- (1-undecyl)dodecyl-5,11-dιhexylcoronene-2,3:8,9-tetracarboxydiimιde was 5.0 g (70percent).
64% at 85℃; Commercially available Perylene-3,4.9,10-tetracarboxylιc dian hydride (100.0 g, 0.255 mol) was brominated with mixture of bromine (29 ml.) and Iodine (2.38 g) in 100percent sulfuric acid (845 ml.) at.~ 85° C. The yield of 1 ,7-dibromoperylene-3,4:9,10-tetracarboxylic dianhydride was 90 g (64percent). Analysis: calculated' C24H6Br2O6, C 52.40, H 1.10, Br 29 05, O 17.45 percent; found: C 52 29, H, 1 07, Br 28, 79 percent Absorption spectrum (9 82x105 M solution in 93percent sulfuric acid): 405 (9572), 516 (27892), 553 (37769).N.N'-Dicyclohexyl-I J-dibromoperylene-S^.ψ.IO-tetracarboxydiimide was synthesized by reaction of 1 ,7-dιbromoperylene-3,4.9,10-tetracarboxylιc dianhydride (30.0 g) with cyclohexylamine (18.6 mL) in N-methylpyrrolidone (390 mL) at -85 ° C. The yield of N,N'-dιcyclohexyl-1 ,7- dibromoperylene-3,4:9,10-tetracarboxydiimιde was 30 g (77percent). N.N'-Dicyclohexyl-I J-dKoct-i-ynyOperylene-S^ ψ.IO-tetracarboxydiimide by Sonogashira reaction: N.N'-dicyclohexyl-I J-dibromperylene-S^ ψ.IO-tetracarboxydiimide (24.7 g) and octyne-1 (15 2 g) in the presence of bis(triphenylphosphine)palladium(ll) chloride (2.42 g), triphenylphospine (0 9 g),and copper(l) iodide (0.66 g). The yield of N.N'-dicyclohexyl-I J-d^oct-i-ynyOperylene-Sλψ.IO- tetracarboxydiimide was 15.7 g (60 percent). N,N'-Dicyclohexyl-5,11-dιhexylcoronene-2,3:8,9-tetracarboxydiimιde was synthesized by heating of N,N'-dicyclohexyl-1 ,7-dι(oct-1-ynyl)perylene-3,4.9,10-tetracarboxydιιmide (7.7 g) in toluene (400 mL) in the presence of 1 ,8-Dιazabιcyclo[5.4.0]undec-7-ene (0.6 ml) at 100-110° C for 20 hours. 5,1 i-dihexylcoronene^.S'δ.ψ-tetracarboxylic dianhydride was prepared by hydrolysis of N1N'- dicyclohexyl-5,11-dihexylcoronene-2,3:8,9-tetracarboxydiimide (6 4 g, 8 3 mmol) with Potassium hydroxide (7 0 g, 85percent) in the mixture of tert-butanol (400 mL) and water (0.4 mL) at 85-90°C The yield of 5,1 i-dihexylcoronene^S'δ.ψ-tetracarboxylic dianhydride was 4 2 g (83percent). <n="20"/>N,N'-(1-undecyl)dodecyl-5,11-dιhexylcoronene-2,3:8,9-tetracarboxydiimιde by the reaction of 5,11-di(hexyl)coronene-2,3:8,9-tetracarboxylic dianhydride with 12-tπcosanamine. 5,11- di(hexyl)coronene-2,3.8,9-tetracarboxylιc dianhydride (3.44 g), 12-tπcosanamine (7.38 g), benzoic acid (45 mg) and 3-chlorophenol (15 mL) was evacuated and saturated with argon two times at room temperature and 2 times at 1000C The reaction mixture was agitated at ~140°C for 1 hour and 160- 165°C for 20 hours in a flow of argon After that the reaction mixture was agitated at ~100°C and was vacuumed at 10 mm Hg for half an hour. Then apparatus was filled with argon once again and heating was continued for the next 24 hours The yield of preparation of N,N'-(1-undecyl)dodecyl-5,11- dihexylcoronene-2,3.8,9-tetracarboxydιιmide was 5.0 g (70percent).
60%
Stage #1: at 20℃; for 2 h;
Stage #2: at 80℃; for 18 h;
Perylene-3 ,4,9,10-tetracarboxylic dianhydride (Perylene-3 ,4,9,10-tetracarboxylic dianhydride) 16g (0.0407mol), iodine (iodine) 0.39g (0.00152mol), 98percent sulfuric acid (sulfuric acid) 225ml at room temperature And stirred (stirring) at room temperature for 2 hours. Raising the temperature to 80° and slowly added bromine (bromine) 4.6ml (0.09mol) over 2 hours. After reaction for 16 hours while maintaining the temperature, it cooled to room temperature to remove the remaining bromine with nitrogen gas. The ice bath under reduced pressure, the resulting precipitate was slowly poured into distilled water 2000ml under (Ice-bath) and filtered. Distillation until pH = 7 Then washed with water several times and dried in a vacuum oven waterway. Material to be produced in the present synthesis process is a mixed state of bromine is substituted one or two substances and substituted material, so that little or no solubility was purified in the next step. The final product yield to 9.624g exhibited a 60percent
42%
Stage #1: at 20℃; for 2 h;
Stage #2: at 80℃; for 20 h;
first,32 g of perylenetetracarboxylic anhydride and 1 g of iodine (I2) were placed in 450 ml of sulfuric acid and stirred at room temperature for 2 hours.to the next,The temperature of the reaction mixture was raised to 80°C and, using a dropping funnel,9.5 ml of bromine (Br2) was added dropwise over 3 hours and then reacted under reflux conditions for 17 hours.After completion of the reaction, nitrogen gas was blown to remove remaining bromine gas,The reaction mixture was cooled to room temperature,Slowly poured into 3 L of ice water to form a precipitate. after, The precipitate was filtered and washed several times with distilled water,The filtered material was oven dried, Compound 1-4a in which the bromine atom was substituted at the bay-position (1, 7-position of the perylene) was obtained in a yield of 42.8percent.
6 g
Stage #1: With iodine In sulfuric acid at 50℃; for 12 h;
Stage #2: With bromine In sulfuric acid at 80℃; for 48 h;
A mixture of 5.0 g (13 mmol) of perylene-3,4:9,10-tetraboxylicacid bisanhydride (1) and sulfuric acid (100 mL) was stirred at 50 C for 12 h, and subsequently I2 (0.56 g) was added. The reaction mixture was heated to 80 C, and bromine 2.2 g (15 mmol) was added dropwise over a time period of 2 h. After bromine addition, the reaction mixture was heated for an additional 48 h, the excess bromine was removed by saturated aqueous solution of K2CO3, and water (100 mL) was added carefully. The precipitate was separated by filtration, washed with water (100 mL), and dried in a vacuum to give a red powder 6.0 g. Without further purification it was used to the next reaction.

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YieldReaction ConditionsOperation in experiment
92% at 65℃; for 30 h; A mixture of 3,4,9,10-perylenetetracarboxylic dianhydride(3.30 g, 8.41 mmol), chlorosulfonic acid (20 mL, 300 mmol) andiodine (0.56 g, 2.20 mmol) was stirred at 65 C for 30 h. Aftercooling to room temperature, the solution was added dropwise toan ice-water mixture. The precipitate was collected by filtration togive a red solid (4.14 g, 92percent). 1H NMR (d-DMSO, ppm): 8.75 (s, 4H,aromatic protons). 13C NMR (d-DMSO, ppm): 119.75, 125.29, 129.5,134.88, 136.22, 158.16, 168.53. Mass (EI): m/z 532.
74.4% at 20 - 70℃; for 6.33333 h; Inert atmosphere 10253] (Compound (Id) Manufacturing Process)10254] Chlorosulfuric acid (500 g, 4.29 mol) was inserted into a 1000 ml three neck flask under an argon gas flow. 3,4,9,10-perylene tetracarboxylic acid dianhydride (50 g,0.127 mol) was added to the chlorosulfuric acid for 20 minutes at the room temperature and then iodine (8.5 g, 0.024 mol) was added. 10255] Then, the temperature of the reaction liquid was increased up to 70° C., and reaction was performed with stirring for 6 hours.10256] After the reaction was completed, the reaction liquidwas cooled such that the temperature became the room temperature, and quenching was performed with cool water(2000 ml). The reaction liquid was discolored from dark brown to scarlet and crystals were precipitated. These crystals were taken out, and subjected to slurry washing with water (1000 ml) three times. Then, slurry washing was performed three times with acetonitrile (500 ml), and taken crystals were dried. Thus, a compound (abbreviated to a “compound (1)- bid”) which was represented by the following formula (1)- bid, as the compound (Id) was obtained (collected amount:50.1 g, and yield: 74.4percent).10257] It was confirmed that the compound (1)-bid was obtained, by MS measurement, ion chromatography, and IR measurement. For example, a spectrum of a pro-ion peak mlz=530 was confirmed in the MS measurement. It was confirmed that a chlorine content was 25.1percent (ideal value: 26.8percent) by using an oxygen combustion method in the ion chromatography.
74.4%
Stage #1: at 20℃; for 0.333333 h; Inert atmosphere
Stage #2: at 70℃; for 6 h;
First, a reaction represented by the reaction formula (1-11) was performed as a reaction process 1.500 g of chlorosulthric acid (4.29 mol) was added to 1000 mE of a three-necked flask through argon gas, and 50 g (0.127mol) of 3,4,9,10-perylenetetracarboxylic acid dianhydridewas added thereto at room temperature for 20 minutes. Next, 8.5 g (0.024 mol) of iodine was added thereto. The tempera- tare of the obtained reaction liquid was increased to 70° C., and the reaction liquid was reacted by stirring for 6 hours.After the reaction was terminated, the temperature of the reaction liquid was cooled to the room temperature, 2000 mE of ice water was added thereto, and then the reaction liquid was quenched. The color of the reaction liquid was changed from dark brown into vermilion and crystals were deposited. The crystals were collected by filtration to be slurry-washed using 1000 mE of water for three times. Subsequently, slurry washing was thrther performed using 500 mE of acetonitrile for three times. The collected crystals by filtration were dried. The wet weight of an obtained product was 102 g, the dry 25 weight thereof was 50.1 g, and the yield thereof was 74.4percent.
62.2% at 70℃; for 5 h; In a 100 ml three-necked flask equipped with a reflux condenser and two glass stoppers 3,4:9,10-perylene tetracarboxylic dianhydride (1 g, 2.55 mmol) and iodine (170 mg, 0.67 mmol) were dissolved in chlorosulfonic acid (10 ml). The mixture was heated to 70 °C for 5 h. Afterwards the reaction mixture was poured into an ice-water mixture and the insoluble product was collected by filtration. The crude product was purified by soxhlet extraction using dichloromethane as solvent. The solvent was evaporated by the rotary evaporator to yield a red solid. Yield 2.3 g (62.2percent) IR (ν(cm-1)): ν=1080 [C-Cl aromatic], 1475-1600 [aromatic stretch], 1700 [CO anhydride], 3000 [C-H aromatic], Elemental analysis for chlorine: calculated: 26.75percent measured: 23.4-23.93percent.

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