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Product Details of [ 1312703-28-8 ]

CAS No. :1312703-28-8 MDL No. :MFCD30489603
Formula : C20H15NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :IONBHNFWEFNUEE-UHFFFAOYSA-N
M.W : 333.34 Pubchem ID :89027256
Synonyms :

Safety of [ 1312703-28-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1312703-28-8 ]

* 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.

  • Downstream synthetic route of [ 1312703-28-8 ]

[ 1312703-28-8 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 1312703-30-2 ]
  • [ 1312703-28-8 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: dimethyl 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylate With potassium hydroxide In ethanol; water at 60℃; Reflux; Stage #2: With hydrogenchloride In water
95% With water; potassium hydroxide In tetrahydrofuran 1 Dissolve 2'-amino-[1,1':4',1”-terphenyl]-4,4”-dimethyl in 35 ml of tetrahydrofuran and stir, add potassium hydroxide aqueous solution (2mol/L) , Stir at 55°C for 12 hours.After that, the solvent was distilled under reduced pressure, dissolved in water, then acidified by adding trifluoroacetic acid to pH less than 2, filtered, washed with water, and dried in a vacuum drying oven to obtain the final product 2'-amino-[1,1':4',1 "-Terphenyl]-4,4"-dicarboxylic acid, the yield is 95%.
90% Stage #1: dimethyl 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylate With potassium hydroxide In tetrahydrofuran; methanol at 40℃; for 20.5h; Stage #2: With trifluoroacetic acid In tetrahydrofuran at 20℃; for 1.5h;
90% Stage #1: dimethyl 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylate With potassium hydroxide In tetrahydrofuran; methanol at 40℃; for 16h; Stage #2: With trifluoroacetic acid In tetrahydrofuran at 20℃; for 1.5h;
90% Stage #1: dimethyl 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylate With potassium hydroxide In methanol at 40℃; for 16h; Inert atmosphere; Schlenk technique; Stage #2: With trifluoroacetic acid In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere; Schlenk technique;
81.4% With potassium hydroxide In tetrahydrofuran; water at 50℃; for 12h;
80% Stage #1: dimethyl 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylate With potassium hydroxide In tetrahydrofuran; methanol at 40℃; for 18h; Stage #2: With trifluoroacetic acid In tetrahydrofuran; methanol at 20℃; for 2h;
80% Stage #1: dimethyl 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylate With potassium hydroxide In tetrahydrofuran; methanol at 40℃; for 18h; Stage #2: With trifluoroacetic acid In tetrahydrofuran at 20℃; for 2h; 9.1 9.1. Synthesis and characterization of UiO-66, UiO-67, and amino UiO- 68 Hf NMOFs The amino-triphenyldicarboxyl methyl ester from above (1 .68 g, 4.65 mmol) was suspended in 200 mL of THF and heated to 40°C. To the suspension 100 mL of 5.5 M KOH methanol solution was added and the resulting mixture was stirred at 40 °C for 18 hours. A white solid was collected by centrifugation, and then treated with 12 mL of trifluoroacetic acid in 100 mL of THF at room temperature for 2 h. The yellow solid product (amino-TPDC) was isolated by vacuum filtration and washed with THF, methanol and ether. Yield: 80%. H NMR (DMSO-d6): δ =12.97 (br, 2H), 8.03 (m, 4H), 7.74 (d, 2H), 7.61 (d, 2H), 7.16 (d, 2H), 7.02 (dd, 1 H), 5.12 (br, 2H). 3C NMR (DMSO-d6): δ =167.66, 167.63 (COOH), 146.24 (C ), 145.00 (Cr), 144.25 (d), 139.96 (C4 ), 131 .31 (C63 FontWeight="Bold" FontSize="10" , C3), 129.98, 129.54 (C4 FontWeight="Bold" FontSize="10" , C4), 129.19 (C2 FontWeight="Bold" FontSize="10" ), 126.97 (C2), 125.04 (C2>), 1 15.96 (C5<), 1 14.26 (C3.).
80% Stage #1: dimethyl 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylate With potassium hydroxide In tetrahydrofuran; methanol at 40℃; for 18h; Stage #2: With trifluoroacetic acid at 20℃; for 2h;
72.8% With potassium hydroxide In tetrahydrofuran at 50℃; for 12h;
Stage #1: dimethyl 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylate With methanol; potassium hydroxide Stage #2: With water; trifluoroacetic acid
With water; potassium hydroxide In tetrahydrofuran; methanol at 40℃; for 12h; 1 example 1 Into a 100 mL single-necked flask was placed Intermediate A (1.66 mmol, 0.60 g), THF (20 mL) and MeOH (20 mL)After complete dissolution of the body, an aqueous solution of 10 mL of KOH (3.0 g, 53.6 mmol) was added, stirred at 40 ° C at constant temperature for 12 h,After removal of THF and MeOH under reduced pressure, 100 mL of distilled water was added and the pH was adjusted to <2 with dilute hydrochloric acid. Yellow-green solid precipitation, filtration, useWashed three times with water, and air-dried at room temperature to obtain 0.45 g of a yellow-green solid powder of Compound I in a yield of 81.45%.
Stage #1: dimethyl 2’-amino-1,1’:4,1’’-terphenyl-4,4’’-dicarboxylate With potassium hydroxide In tetrahydrofuran; methanol Stage #2: With trifluoroacetic acid In tetrahydrofuran
With potassium hydroxide In tetrahydrofuran; methanol at 20℃; for 12h; Inert atmosphere; 8 Example 8 MOFs with Salicylaldimine-Based Bridging Ligands An MOF comprising a salicylaldimine-based bridging ligand (H2SALI-TPD) was prepared. The synthesis of ligand was accomplished as shown in Scheme 15. Hydrothermal reactions between H2SALI-TPD and ZrCl4 led to crystalline SALI-MOF. PXRD studies indicated that SALI-MOF remained crystalline upon treatment with FeCl3 to form SALI-MOF-Fe as comparative to the crystalline MOF, i.e., UiO-68-NH2, that is composed of Zr6(μ3-O)4(μ3-OH)4 SBUs and amino-terphenyldicarboxylated bridging ligands. Nitrogen surface area measurements indicated that SALI-MOF is highly porous with a BET surface area of 3330 m2/g. Upon treatment with NaBEt3H in THF, we found that the SALI-MOF-Fe is highly active in alkene hydrogenation reactions, with a TON of >30,000. See Table 8. (0219) Exemplary Procedure for SALI-MOF-Fe Catalyzed Hydrogenation of Olefins: (0220) In a glovebox, SALI-MOF-Fe in THF (3.0 mg, 0.1 mol % Fe) was quickly weighed onto a filter paper, charged into a small vial and 1 mL THF was added. Then, 15 μL NaEt3BH (1.0 M in THF) was added to the vial and the mixture was stirred slowly for 1 h in the glovebox. During stirring, the solid became greenish black. The solid was centrifuged out of suspension and washed with THF 2-3 times. Then, the solid in 1 ml THF was transferred to a vial and olefin (1.56 mmol) was added. The vial was placed into a Parr pressure reactor in a nitrogen-filled glovebox. The reactor was then pressurized to 40 bar. After stirring at room temperature for 15-24 h, the solid was centrifuged out of suspension and extracted 2-3 times with THF. The combined organic extracts were concentrated in vacuo and purified either by silica gel preparative TLC or fractional distillation to yield the pure product. (0221) [table-us-00008-en] TABLE 8 SALI-MOF-Fe catalyzed hydrogenation reactions. Entry Olefin Product Time (h) Yield (%) 1 2 15 18 100 100b 24 30 c 3 4 18 18 100 95b 5 18 12 6 18 100 7 18 100 8 24 100 9 10 18 24 100 45 c
With potassium hydroxide In tetrahydrofuran; methanol at 70℃; Inert atmosphere; Schlenk technique;
With potassium hydroxide In tetrahydrofuran; methanol at 70℃; for 12h; Inert atmosphere;

Reference: [1]Li, Tao; Kozlowski, Mark T.; Doud, Evan A.; Blakely, Maike N.; Rosi, Nathaniel L. [Journal of the American Chemical Society, 2013, vol. 135, # 32, p. 11688 - 11691]
[2]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN111054443, 2021, B Location in patent: Paragraph 0050; 0053-0054
[3]Location in patent: experimental part Schaate, Andreas; Roy, Pascal; Godt, Adelheid; Lippke, Jann; Waltz, Florian; Wiebcke, Michael; Behrens, Peter [Chemistry - A European Journal, 2011, vol. 17, # 24, p. 6643 - 6651]
[4]Carboni, Michal; Lin, Zekai; Abney, Carter W.; Zhang, Teng; Lin, Wenbin [Chemistry - A European Journal, 2014, vol. 20, # 46, p. 14965 - 14970]
[5]Manna, Kuntal; Zhang, Teng; Carboni, Michaël; Abney, Carter W.; Lin, Wenbin [Journal of the American Chemical Society, 2014, vol. 136, # 38, p. 13182 - 13185]
[6]Li, Yan-An; Yang, Song; Liu, Qi-Kui; Chen, Gong-Jun; Ma, Jian-Ping; Dong, Yu-Bin [Chemical Communications, 2016, vol. 52, # 39, p. 6517 - 6520]
[7]He, Chunbai; Lu, Kuangda; Liu, Demin; Lin, Wenbin [Journal of the American Chemical Society, 2014, vol. 136, # 14, p. 5181 - 5184]
[8]Current Patent Assignee: UNIVERSITY OF CHICAGO - WO2016/61256, 2016, A1 Location in patent: Page/Page column 91
[9]Wei, Yuan-Ping; Liu, Yi; Guo, Fan; Dao, Xiao-Yao; Sun, Wei-Yin [Dalton Transactions, 2019, vol. 48, # 23, p. 8221 - 8226]
[10]Cao, Chen-Chen; Chen, Cheng-Xia; Wei, Zhang-Wen; Qiu, Qian-Feng; Zhu, Neng-Xiu; Xiong, Yang-Yang; Jiang, Ji-Jun; Wang, Dawei; Su, Cheng-Yong [Journal of the American Chemical Society, 2019, vol. 141, # 6, p. 2589 - 2593]
[11]Current Patent Assignee: UNIVERSITY OF NORTH CAROLINA SYSTEM; UNIVERSITY OF CHICAGO - WO2015/69926, 2015, A1 Location in patent: Page/Page column 67
[12]Current Patent Assignee: SHANDONG UNIVERSITY - CN105669779, 2016, A Location in patent: Paragraph 0037; 0039
[13]Mieno; Kabe; Allendorf; Adachi [Chemical Communications, 2018, vol. 54, # 6, p. 631 - 634]
[14]Current Patent Assignee: UNIVERSITY OF CHICAGO - US10647733, 2020, B2 Location in patent: Page/Page column 41-42
[15]Akhtar, Naved; Antil, Neha; Balendra; Begum, Wahida; Kumar, Ajay; Manna, Kuntal; Newar, Rajashree; Shukla, Sakshi [Inorganic Chemistry, 2020, vol. 59, # 15, p. 10473 - 10481]
[16]Newar, Rajashree; Akhtar, Naved; Antil, Neha; Kumar, Ajay; Shukla, Sakshi; Begum, Wahida; Manna, Kuntal [Angewandte Chemie - International Edition, 2021, vol. 60, # 19, p. 10964 - 10970][Angew. Chem., 2021, vol. 133, # 19, p. 11059 - 11065,7]
  • 2
  • [ 1312703-28-8 ]
  • [ 20039-33-2 ]
  • C25H25N2O8P [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 50℃; for 24h;
  • 3
  • [ 1312703-28-8 ]
  • [ 10026-11-6 ]
  • [ 65-85-0 ]
  • Zr6O4(OH)4(2′-amino-[1,1′:4′,1″-terphenyl]-4,4″-dicarboxylate)6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 70℃; for 72h;
  • 4
  • [ 1312703-28-8 ]
  • 3C14H8N2O4(2-)*4Zn(2+)*2C5H4N5(1-)*O(2-) [ No CAS ]
  • 4Zn(2+)*2C5H4N5(1-)*O(2-)*3C20H13NO4(2-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 75℃; for 48h;
  • 5
  • [ 108-30-5 ]
  • [ 1312703-28-8 ]
  • C24H19NO7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% In dimethyl sulfoxide at 20℃; for 24h;
  • 6
  • [ 108-31-6 ]
  • [ 1312703-28-8 ]
  • C24H17NO7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% In dimethyl sulfoxide at 20℃; for 24h;
  • 7
  • [ 3638-73-1 ]
  • [ 1312703-28-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: cesium fluoride; palladium diacetate; triphenylphosphine / tetrahydrofuran / 48 h / 60 °C 2.1: potassium hydroxide / tetrahydrofuran; methanol / 16 h / 40 °C 2.2: 1.5 h / 20 °C
Multi-step reaction with 2 steps 1.1: cesium fluoride; palladium diacetate; triphenylphosphine / tetrahydrofuran / 48 h / 60 °C / Inert atmosphere; Schlenk technique 2.1: potassium hydroxide / methanol / 16 h / 40 °C / Inert atmosphere; Schlenk technique 2.2: 1.5 h / 20 °C / Inert atmosphere; Schlenk technique
Multi-step reaction with 2 steps 1: palladium diacetate; cesium fluoride; triphenylphosphine / tetrahydrofuran / 12 h / Reflux; Inert atmosphere 2: potassium hydroxide / tetrahydrofuran; methanol / 12 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: palladium diacetate; sodium carbonate / N,N-dimethyl-formamide; water / 16 h / 105 °C / Schlenk technique; Inert atmosphere 2: potassium hydroxide / methanol; tetrahydrofuran / 70 °C / Inert atmosphere; Schlenk technique

  • 8
  • [ 99768-12-4 ]
  • [ 1312703-28-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: cesium fluoride; palladium diacetate; triphenylphosphine / tetrahydrofuran / 48 h / 60 °C 2.1: potassium hydroxide / tetrahydrofuran; methanol / 16 h / 40 °C 2.2: 1.5 h / 20 °C
Multi-step reaction with 2 steps 1.1: cesium fluoride; palladium diacetate; triphenylphosphine / tetrahydrofuran / 48 h / 60 °C / Inert atmosphere; Schlenk technique 2.1: potassium hydroxide / methanol / 16 h / 40 °C / Inert atmosphere; Schlenk technique 2.2: 1.5 h / 20 °C / Inert atmosphere; Schlenk technique
Multi-step reaction with 2 steps 1: palladium diacetate; cesium fluoride; triphenylphosphine / tetrahydrofuran / 12 h / Reflux; Inert atmosphere 2: potassium hydroxide / tetrahydrofuran; methanol / 12 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: palladium diacetate; sodium carbonate / N,N-dimethyl-formamide; water / 16 h / 105 °C / Schlenk technique; Inert atmosphere 2: potassium hydroxide / methanol; tetrahydrofuran / 70 °C / Inert atmosphere; Schlenk technique

  • 9
  • [ 1312703-28-8 ]
  • [ 90-02-8 ]
  • H2SALI-TPD [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% In methanol; water; dimethyl sulfoxide for 24h; Inert atmosphere; Schlenk technique;
In methanol; dimethyl sulfoxide for 12h; Inert atmosphere; 8 Example 8 MOFs with Salicylaldimine-Based Bridging Ligands An MOF comprising a salicylaldimine-based bridging ligand (H2SALI-TPD) was prepared. The synthesis of ligand was accomplished as shown in Scheme 15. Hydrothermal reactions between H2SALI-TPD and ZrCl4 led to crystalline SALI-MOF. PXRD studies indicated that SALI-MOF remained crystalline upon treatment with FeCl3 to form SALI-MOF-Fe as comparative to the crystalline MOF, i.e., UiO-68-NH2, that is composed of Zr6(μ3-O)4(μ3-OH)4 SBUs and amino-terphenyldicarboxylated bridging ligands. Nitrogen surface area measurements indicated that SALI-MOF is highly porous with a BET surface area of 3330 m2/g. Upon treatment with NaBEt3H in THF, we found that the SALI-MOF-Fe is highly active in alkene hydrogenation reactions, with a TON of >30,000. See Table 8. (0219) Exemplary Procedure for SALI-MOF-Fe Catalyzed Hydrogenation of Olefins: (0220) In a glovebox, SALI-MOF-Fe in THF (3.0 mg, 0.1 mol % Fe) was quickly weighed onto a filter paper, charged into a small vial and 1 mL THF was added. Then, 15 μL NaEt3BH (1.0 M in THF) was added to the vial and the mixture was stirred slowly for 1 h in the glovebox. During stirring, the solid became greenish black. The solid was centrifuged out of suspension and washed with THF 2-3 times. Then, the solid in 1 ml THF was transferred to a vial and olefin (1.56 mmol) was added. The vial was placed into a Parr pressure reactor in a nitrogen-filled glovebox. The reactor was then pressurized to 40 bar. After stirring at room temperature for 15-24 h, the solid was centrifuged out of suspension and extracted 2-3 times with THF. The combined organic extracts were concentrated in vacuo and purified either by silica gel preparative TLC or fractional distillation to yield the pure product. (0221) [table-us-00008-en] TABLE 8 SALI-MOF-Fe catalyzed hydrogenation reactions. Entry Olefin Product Time (h) Yield (%) 1 2 15 18 100 100b 24 30 c 3 4 18 18 100 95b 5 18 12 6 18 100 7 18 100 8 24 100 9 10 18 24 100 45 c
  • 10
  • [ 1312703-28-8 ]
  • [ 10026-11-6 ]
  • Zr6O4(OH)4(2′-amino-[1,1′:4′,1″-terphenyl]-4,4″-dicarboxylate)6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 120℃; for 16h; Autoclave; High pressure;
  • 11
  • [ 3638-73-1 ]
  • [ 99768-12-4 ]
  • [ 1312703-28-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); cesium fluoride / tetrahydrofuran / 48 h / Inert atmosphere; Reflux 2: potassium hydroxide / tetrahydrofuran; water / 12 h / 50 °C
Multi-step reaction with 2 steps 1.1: cesium fluoride; palladium diacetate; triphenylphosphine / tetrahydrofuran / 48 h / 50 °C / Inert atmosphere 2.1: potassium hydroxide / tetrahydrofuran; methanol / 18 h / 40 °C 2.2: 2 h / 20 °C
Multi-step reaction with 2 steps 1: palladium diacetate; sodium carbonate / N,N-dimethyl-formamide; water / 6 h / 105 °C / Inert atmosphere; Schlenk technique 2: potassium hydroxide / tetrahydrofuran / 12 h / 50 °C
Multi-step reaction with 2 steps 1: palladium diacetate; sodium carbonate / N,N-dimethyl-formamide; water / 16 h / 105 °C / Inert atmosphere; Schlenk technique 2: potassium hydroxide / methanol; tetrahydrofuran / 12 h / 70 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: cesium fluoride; palladium diacetate; triphenylphosphine / tetrahydrofuran / 48 h / 60 °C / Inert atmosphere 2: potassium hydroxide; water / tetrahydrofuran

  • 12
  • [ 64-17-5 ]
  • [ 1312703-28-8 ]
  • [ 33513-42-7 ]
  • lead(II) chloride [ No CAS ]
  • 1.5Pb(2+)*C20H13NO4(2-)*Cl(1-)*H2O*2C2H6O*C3H7NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With perchloric acid High pressure; Heating;
  • 13
  • [ 1312703-28-8 ]
  • C20H13NO4(2-)*Mg(2+)*2H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With magnesium(II) nitrate; water In methanol; N,N-dimethyl-formamide at 95℃; for 40h; 4 The invention also provides a preparation method of the magnesium metal organic complex, which comprises the following steps:Adding 2'-amino-1,1':4',1"-terphenyl-4,4"-dicarboxylic acid and magnesium acetate to the solvent,After stirring uniformly, it was placed in a stainless steel reaction vessel of a polytetrafluoroethylene liner and reacted at 100 ° C for 35 hours.After the reaction is completed, the magnesium is cooled, filtered, washed and dried to obtain the magnesium.Metal organic complex.
  • 14
  • [ 1312703-28-8 ]
  • [ 13499-05-3 ]
  • Hf-DBA [ No CAS ]
YieldReaction ConditionsOperation in experiment
44.1% With trifluoroacetic acid In N,N-dimethyl-formamide at 60℃; for 72h;
  • 15
  • [ 1121-60-4 ]
  • [ 1312703-28-8 ]
  • C26H18N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% In methanol; dimethyl sulfoxide at 20℃; for 16h; Schlenk technique; Inert atmosphere;
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