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Butler, Tristan ; Bunton, Caleb ; Ryou, Heonjune , et al. DOI:

Abstract: This effort assesses the correlation between chem. structures and performance-essential thermal, mech., and long-term stability properties of cross-linked thermosets. Resins of different mol. weights were prepared from the Bisphenol A based PEEK-like oligomeric phthalonitrile (BisA). Differential scanning calorimetry, which was used to investigate curing thermodn., indicated that BisA resins demonstrated pos. correlation between increasing oligomer mol. weight and both resulting m.ps. and cure initiation conditions. Characterization of thermal properties using thermogravimetric anal. (TGA) indicated a similar mol. weight trend, with char yields ranging between 57% and 73%. Rheol. studies of BisA of different mol. weights indicated significant viscosity increases in phthalonitriles that crosslinked from oligomers with higher mol. weights Moreover, the n = 1 chain length resin exhibited a gel point at 100°C lower than the n = 25 oligomer. Anal. of hardness of these cured polymers indicated that the resin crosslinked using the n = 1 oligomer was most brittle, while the thermoset derived from the n = 4 BisA demonstrated highest hardness. Aging of cured phthalonitriles indicated that the n = 10 remained most stable in long-duration high-temperature environments. This study suggests the use of preparing BisA thermosets from oligomers with different mol. weights as an effective strategy for improving toughness, albeit at the tradeoff of lower thermal stabilities.

Keywords: mechanical properties ; resins ; thermal properties ; thermosets

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Product Details of [ 31643-49-9 ]

CAS No. :31643-49-9 MDL No. :MFCD00040301
Formula : C8H3N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NTZMSBAAHBICLE-UHFFFAOYSA-N
M.W : 173.13 Pubchem ID :97443
Synonyms :

Calculated chemistry of [ 31643-49-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.69
TPSA : 93.4 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.75
Log Po/w (XLOGP3) : 1.34
Log Po/w (WLOGP) : 1.34
Log Po/w (MLOGP) : -0.32
Log Po/w (SILICOS-IT) : -0.37
Consensus Log Po/w : 0.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.6 mg/ml ; 0.00927 mol/l
Class : Soluble
Log S (Ali) : -2.9
Solubility : 0.216 mg/ml ; 0.00125 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.95
Solubility : 1.96 mg/ml ; 0.0113 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.99

Safety of [ 31643-49-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 31643-49-9 ]

* 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 [ 31643-49-9 ]
  • Downstream synthetic route of [ 31643-49-9 ]

[ 31643-49-9 ] Synthesis Path-Upstream   1~18

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Reference: [1] RSC Advances, 2015, vol. 5, # 96, p. 79207 - 79215
[2] Patent: CN104910113, 2017, B,
  • 2
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YieldReaction ConditionsOperation in experiment
89% With thionyl chloride In N,N-dimethyl-formamide at 5℃; for 18 h; Inert atmosphere The thionyl chloride (286mol) was slowly added to 50mL of N,N-dimethylformamide at a temperature lower than 5°C, was stirred in an argon atmosphere. 15g of 4-nitrophthalamide was added and the reaction was maintained for 18h. The crude product was precipitated from a mixture of water–ice [1]. Yield 89percent; 1H NMR (300MHz, DMSO-d6; δ: ppm): 8.44 (d, J=8.7, 1H, H−Ar); 8.68 (dd, J=2.1Hz, J=8.4Hz, 1H, H−Ar); 9.04 (d, J=2.1, 1H, H−Ar). 13C NMR (75MHz, DMSO-d6, δ): 114.55; 114.86; 116.60; 120.22; 128.53; 128.81; 135.27; 149.70. FTIR: 3090 (C−H aromatic); 2245 (CN); 1534 (asymmetric N−O band); 1351 (symmetric N−O band); 852 (C−N).
79.9% With trifluoroacetic anhydride In 1,4-dioxane; water Example 3
Preparation of 4-nitrophthalonitrile
25g of 4-nitrophthalic amide prepared according to Example 1 was added to 210 ml dry dioxane (supplied by Aldrich) and the mixture was cooled to 0°C. 42 ml of trifluoroacetic anhydride was slowly added to the mixture over a period of three hours.
The mixture was then allowed to warm to room temperature whilst being stirred and a clear solution was formed.
The mixture was diluted with 700 ml of water and extracted four times with 200 ml aliquots of ethyl acetate.
The extracts were combined and washed successively with water, dilute hydrochloric acid (10percent v/v), water and 5percent w/vaqueous sodium chloride solution.
The solvent was evaporated on a rotary evaporator and the resultant solid product was recrystallized from 50/70 (v/v) acetone/hexane mixture to yield 14 g of 4-nitrophthalonitrile crystals.
Further evaporation of the mother liquor and recrystallisation increased the total yield to 79.9percent.
Theoretical analysis of C8H3N3O2: C,55.49percent, H,1.73percent; N,24.27percent; found: C,55.32percent; H,1.63percent; N,24.18percent.
This preparation method is described by T.W.
Hall et al in Nouveau J.de Chimie, 1982 6 653.
50% With trichlorophosphate In pyridine 4-nitrophthalonitrile (II)
4-nitrophthalamide (220g; 1.05 moles) is suspended in pyridine (840ml).
Into this vigrously stirred suspension, phosphorus oxychloride (220 ml; 2.40 moles) is added at such a rate that the reaction maintains a temperature range of 65°-70° C during the 30 minute addition time.
The same temperature is maintained an additional hour by external heating.
The resulting mixture is neutralized with 12 N hydrochloric acid (150 ml).
The purple solid is collected by filtration and dried.
The residue is extracted with ethyl acetate (3 * 700 ml) and the purple extract is decolorized with activated charcoal, washed first with 0.4 N sodium hydroxide saturated with sodium chloride (3 * 70 ml) and then with water (4 * 70 ml).
Drying and evaporation of the extract leaves 91g of II as pale yellow crystals; yield, 50percent, mp142°-144° C; lit. (7) mp 138°-139° C; lit. (4) 142° C.
Reference: [1] Acta Chemica Scandinavica, 1999, vol. 53, # 9, p. 714 - 720
[2] Materials Research Bulletin, 2016, vol. 75, p. 144 - 154
[3] Heterocycles, 1984, vol. 22, # 9, p. 2047 - 2052
[4] Patent: EP413415, 1991, A1,
[5] Russian Chemical Bulletin, 2003, vol. 52, # 1, p. 150 - 153
[6] Synthetic Communications, 1989, vol. 19, # 18, p. 3231 - 3240
[7] Patent: US4056560, 1977, A,
[8] Journal of Organic Chemistry, 1990, vol. 55, # 7, p. 2155 - 2159
[9] Journal of the Chemical Society, Chemical Communications, 1992, # 12, p. 873 - 875
[10] Spectrochimica Acta - Part A Molecular Spectroscopy, 1998, vol. 54 A, # 1, p. 77 - 83
[11] Mendeleev Communications, 2002, vol. 12, # 3, p. 96 - 97
[12] Chemical Physics Letters, 2006, vol. 423, # 4-6, p. 306 - 311
[13] Journal of Porphyrins and Phthalocyanines, 2015, vol. 19, # 4, p. 573 - 581
  • 3
  • [ 91-15-6 ]
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  • [ 51762-67-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 13, p. 2326 - 2335
  • 4
  • [ 136918-14-4 ]
  • [ 31643-49-9 ]
Reference: [1] Journal of Porphyrins and Phthalocyanines, 2015, vol. 19, # 4, p. 573 - 581
[2] Materials Research Bulletin, 2016, vol. 75, p. 144 - 154
  • 5
  • [ 89-40-7 ]
  • [ 31643-49-9 ]
Reference: [1] Journal of Porphyrins and Phthalocyanines, 2015, vol. 19, # 4, p. 573 - 581
[2] Materials Research Bulletin, 2016, vol. 75, p. 144 - 154
  • 6
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Reference: [1] Chemical Physics Letters, 2006, vol. 423, # 4-6, p. 306 - 311
  • 7
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Reference: [1] Chemical Physics Letters, 2006, vol. 423, # 4-6, p. 306 - 311
  • 8
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Reference: [1] Journal of Physics and Chemistry of Solids, 2006, vol. 67, # 11, p. 2282 - 2288
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Reference: [1] Journal of the Chemical Society, 1941, p. 637,639
  • 10
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  • [ 610-27-5 ]
YieldReaction ConditionsOperation in experiment
95% at 60 - 65℃; for 2.45 h; Green chemistry General procedure: Aromatic or aliphatic nitriles (2 mmol) were dissolved in 5 ml of [bmim]HSO4 and the reaction mixture was heated at 60-65 °C for 1-3 h. The progress of reaction was monitored by TLC. After completion of reaction, as checked by TLC, the reaction mixture was poured into water containing crushed ice. The product was precipitated out, filtered and dried. The yield of the final product was high (>90percent) in all cases. All final products obtained were found sufficiently pure so it didn’t need further purification.The filtrate was concentrated under vacuum, washed with diethylether twice and concentrated under high vacuum. After proper drying under reduced pressure, approximately 95percent ionic liquid was recovered from the reaction and compared with the original ionic liquid to check its authenticity. The efficiency of recovered ionic liquid in conversion of nitriles to acids was found unchanged in comparison to the original one and we reused it up to 5-6 cycles without any significant loss of its activity.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 28, p. 3802 - 3804
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  • [ 65610-14-2 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 3, p. 449 - 454
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YieldReaction ConditionsOperation in experiment
85%
Stage #1: With potassium carbonate; sodium nitrite In dimethyl sulfoxide at 160℃; for 5 h;
1) A three-necked flask was charged with 103.9 g (600 mmo 1) of 4-nitro phthalonitrile, 800 mL of dimethyl sulfoxideAfter the powder was dissolved, 91.0 g (660 mmol) of potassium carbonate and 46.0 g (660 mmol) of sodium nitrite were added and heated at reflux to 160 ° C for 5 hours. After cooling to room temperature, the mixture was poured into a large amount of water, A yellow solid was precipitated and evacuated at 110 ° C and dried in vacuo to give 73.3 g of 4-hydroxy phthalonitrile in 85percent yield.
Reference: [1] RSC Advances, 2015, vol. 5, # 96, p. 79207 - 79215
[2] Patent: CN104910113, 2017, B, . Location in patent: Paragraph 0041-0042; 0045-0046
[3] Synthetic Communications, 1989, vol. 19, # 18, p. 3231 - 3240
[4] Russian Journal of General Chemistry, 2011, vol. 81, # 4, p. 768 - 772
  • 13
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Reference: [1] Canadian Journal of Chemistry, 1985, vol. 63, p. 623 - 631
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  • [ 93673-02-0 ]
Reference: [1] Canadian Journal of Chemistry, 1985, vol. 63, p. 623 - 631
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  • [ 30757-50-7 ]
  • [ 23277-29-4 ]
Reference: [1] Synthetic Communications, 1989, vol. 19, # 18, p. 3231 - 3240
  • 16
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  • [ 108-95-2 ]
  • [ 38791-62-7 ]
YieldReaction ConditionsOperation in experiment
86.4% With sodium hydride In tetrahydrofuran for 8 h; Inert atmosphere; Reflux To NaH (0.15 g) and phenol, (0.353 g,0.0375 mol) in THF (15 mL) was added and 4-nitrophthalonitrile(0.50 g, 0.0028 mol), in THF (15 mL) and refluxed for 8 h. The resulting 1,2-diisocyano-4-phenoxybenzene (8) was filtrated and the solid washed with ethyl acetate and both the filtrate and the washing were mixed and evaporated under reduced pressure (Scheme-II). The resulting white precipitate was purified by flash column chromatography using solvent system, ethyl acetate:hexane (1:4). Yield = 0.737 g, percent Yield =86.4, Rf = 0.36 (ethyl acetate:hexane, 1:4). 1H NMR (300 MHz, CDCl3) δ 0.90 (s, 2H), 3.46 (m, 5H,CH) 7.07 (m, 3H, ArH), 13C NMR (300 MHz, CDCl3) δ 71.01,117.45, 119.69, 119.92, 126.95, 127.34, 134.43, 135.20.
32% With potassium carbonate In dimethyl sulfoxide at 20℃; for 48 h; Inert atmosphere General procedure: The C4-substituted phthalonitrile analogs (4a-i) investigated in this study were synthesized according to the literature description [32]. In an atmosphere of argon, a mixture of 4-nitrophthalonitrile (17.5 mmol), the appropriate alcohol (21 mmol) and potassium carbonate (35 mmol) in 15 mL dimethyl sulfoxide (DMSO) was stirred at room temperature for a period of 48 h. The reaction was poured into 100 mL ice cold water and the precipitate was isolated by filtration and washed with 100 mL water. The crude material was dissolved in ethanol, filtered through cotton wool and left to recrystallize at room temperature. Purification of the target phthalonitriles required at least two successive rounds of recrystallization from ethanol.
11.6 g With potassium carbonate In dimethyl sulfoxide at 20℃; for 48 h; Inert atmosphere Under inert gas (N?), 4~Mtro~o~phth.ak>nitrile (9.2 g), phenol (5.0 g), .2CO3 (7.3 g) and DMSO (40 mL) were added into a flask, and were stirred and reacted at room temperature for 48 hrs., then heated to 60 °C and reacted for 2 hrs. After cooled down, the reaction mixture was filtered and the resulted yellow solid was dried to obtain 11.6 g of Compound 1.
11.6 g With potassium carbonate In dimethyl sulfoxide at 20 - 60℃; for 50 h; Inert atmosphere Under inert gas (N2), 4-nitro-o-phthalonitrile (9.2 g), phenol (5.0 g), K2CO3 (7.3 g) and DMSO (40 mL) were added into a flask, and were stirred and reacted at room temperature for 48 hrs., then heated to 60° C. and reacted for 2 his. After cooled down, the reaction mixture was filtered and the resulted yellow solid was dried to obtain 11.6 g of Compound 1.
11.6 g With potassium carbonate In dimethyl sulfoxide at 20 - 60℃; for 50 h; Inert atmosphere 9.2 g of 4-nitrophthalonitrile, 5.0 g of phenol, 7.3 g of potassium carbonate and 40 ml of DMSO were added under the protection of an inert gas such as nitrogen, and the mixture was stirred at room temperature for 48 hours,The mixture was then heated to 60 ° C for 2 hours and then heated. After cooling, the mixture was precipitated and filtered to give a yellow solid which was dried to give 11.6 g of compound 1.

Reference: [1] Asian Journal of Chemistry, 2017, vol. 29, # 3, p. 489 - 495
[2] Russian Journal of Organic Chemistry, 2006, vol. 42, # 4, p. 603 - 606
[3] Journal of Photochemistry and Photobiology A: Chemistry, 2010, vol. 209, # 2-3, p. 232 - 237
[4] Bioorganic Chemistry, 2012, vol. 40, # 1, p. 114 - 124
[5] Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 6.2, p. 964 - 967[6] Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 6, p. 1232 - 1235
[7] Tetrahedron, 2007, vol. 63, # 6, p. 1385 - 1394
[8] Patent: US5149800, 1992, A,
[9] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 16, p. 4829 - 4840
[10] Journal of Molecular Catalysis A: Chemical, 2012, vol. 358, p. 49 - 57
[11] Patent: WO2013/13609, 2013, A1, . Location in patent: Page/Page column 16
[12] Dyes and Pigments, 2014, vol. 109, p. 214 - 222
[13] Patent: US2015/31721, 2015, A1, . Location in patent: Paragraph 0144
[14] Chemistry - A European Journal, 2017, vol. 23, # 44, p. 10616 - 10625
[15] Patent: TWI582078, 2017, B, . Location in patent: Paragraph 0145; 0147; 0148
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Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1980, vol. 50, p. 1874 - 1878[2] Zhurnal Obshchei Khimii, 1980, vol. 50, # 10, p. 2313 - 2318
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Reference: [1] Macromolecules, 2006, vol. 39, # 22, p. 7534 - 7548
[2] Molecular Crystals and Liquid Crystals, 2004, vol. 418, p. 11/[739]-19/[747]
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