Structure of 36997-31-6
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CAS No. : | 36997-31-6 |
Formula : | C9H12N6O3 |
M.W : | 252.23 |
SMILES Code : | NNC(C1=CC(C(NN)=O)=CC(C(NN)=O)=C1)=O |
MDL No. : | MFCD16172194 |
InChI Key : | MNBHRGAIQJFCIO-UHFFFAOYSA-N |
Pubchem ID : | 15320491 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.2% | With hydrazine hydrate; In ethanol; at 80.0℃; for 24.0h; | In a 250mL round-bottomed flask, 100ml of ethanol and 1,3,5-tricarboxylic acid tricresyl ester (1.39g, 5mmol) were added, and then 8ml of hydrazine hydrate was added dropwise, and the reaction was stirred and refluxed at 80C for 24h. After the completion of the reaction, the reaction solution was cooled to room temperature, and a large amount of solid was precipitated and filtered under reduced pressure. The filter cake was washed 3 times with ethanol and dried to obtain pure target compound (3) (1,2,3,5-trihydrazide). Yield 81.2%, |
With hydrazine hydrate; In ethanol; for 8.0h;Reflux; | Synthesis of intermediate product: Weighing Trimethyl benzenetricarboxylate (5.0 g, 0.02 mol), hydrazine hydrate (85%, 3.79 g, 0.065 mol), Add to a 250 mL flask containing 150 mL of ethanol, reflux under magnetic stirring for 8 h, and disperse heat into a beaker containing a large amount of water. Filtration and recrystallization from ethanol, drying to obtain an intermediate product, to be used; Synthesis of Al3+ probe compounds: The intermediate product (5.0 g, 0.02 mol), salicylaldehyde (7.3 g, 0.06 mol) was weighed and added to a 250 mL flask containing 100 mL of DMF.The reaction was stirred magnetically at 90 C for 8 h, and the heat was dispersed into a beaker containing a large amount of water. Filtered and washed three times with ethanol at 0.06 MPa, Drying under vacuum at 60 C gave a white powdery pure Al3+ probe compound. The calculated yield was 96%. | |
With ethanol; hydrazine hydrate; at 20.0℃; for 8.0h; | (1) The trimesic acidTrimethyl ester (5.0g, 0.02mol) and hydrazine hydrate (85%, 3.79g, 0.065mol) were added to a 250mL flask containing 150mL of ethanol, refluxed for 8h under magnetic stirring at room temperature, and dispersed until it was heated to a large amount of water In the beaker, suction filtered and recrystallized with ethanol,After drying, the product trimesic hydrazide is obtained; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In methanol; for 24.0h;Reflux; | General procedure: The ligands H6L1-7 were prepared by similar methods. A representativemethod for I is presented here. A solution of salicylaldehyde(1.46 g, 12 mmol) in MeOH (30 mL) was added to amethanolic suspension of <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>(0.504 g, 2 mmol). The reaction mixture was refluxed on an oilbath. During this period, the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>slowly dissolved and simultaneously a white solid precipitated.After 24 h of reflux, the reaction mixture was cooled at room temperaturefor an hour, the precipitated solid was filtered, washedwith MeOH (2 5 mL) and dried in a desiccator over silica gel.Data for H6L1 (I): Yield 0.954 g (85%). Anal. Calc. for C30H24N6O6(5 6 4): C, 63.83; H, 4.29; N, 14.89. Found: C, 65.31; H, 4.82; N,13.83%. IR data (cm1): 3440 (OAH), 3018 (NAH), 1659 (CO),1563 (CN). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol; for 24.0h;Reflux; | The ligands H6L1-7 were prepared by similar methods. A representativemethod for I is presented here. A solution of salicylaldehyde(1.46 g, 12 mmol) in MeOH (30 mL) was added to amethanolic suspension of <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>(0.504 g, 2 mmol). The reaction mixture was refluxed on an oilbath. During this period, the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>slowly dissolved and simultaneously a white solid precipitated.After 24 h of reflux, the reaction mixture was cooled at room temperaturefor an hour, the precipitated solid was filtered, washedwith MeOH (2 5 mL) and dried in a desiccator over silica gel.Data for H6L1 (I): Yield 0.954 g (85%). Anal. Calc. for C30H24N6O6(5 6 4): C, 63.83; H, 4.29; N, 14.89. Found: C, 65.31; H, 4.82; N,13.83%. IR data (cm1): 3440 (OAH), 3018 (NAH), 1659 (CO),1563 (CN). |
In N,N-dimethyl-formamide; at 90.0℃; for 8.0h; | Synthesis of intermediate product: Weighing Trimethyl benzenetricarboxylate (5.0 g, 0.02 mol), hydrazine hydrate (85%, 3.79 g, 0.065 mol), Add to a 250 mL flask containing 150 mL of ethanol, reflux under magnetic stirring for 8 h, and disperse heat into a beaker containing a large amount of water. Filtration and recrystallization from ethanol, drying to obtain an intermediate product, to be used; Synthesis of Al3+ probe compounds: The intermediate product (5.0 g, 0.02 mol), salicylaldehyde (7.3 g, 0.06 mol) was weighed and added to a 250 mL flask containing 100 mL of DMF. The reaction was stirred magnetically at 90 C for 8 h, and the heat was dispersed into a beaker containing a large amount of water. Filtered and washed three times with ethanol at 0.06 MPa, Drying under vacuum at 60 C gave a white powdery pure Al3+ probe compound. The calculated yield was 96%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | In methanol; for 24.0h;Reflux; | General procedure: The ligands H6L1-7 were prepared by similar methods. A representativemethod for I is presented here. A solution of salicylaldehyde(1.46 g, 12 mmol) in MeOH (30 mL) was added to amethanolic suspension of <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>(0.504 g, 2 mmol). The reaction mixture was refluxed on an oilbath. During this period, the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>slowly dissolved and simultaneously a white solid precipitated.After 24 h of reflux, the reaction mixture was cooled at room temperaturefor an hour, the precipitated solid was filtered, washedwith MeOH (2 5 mL) and dried in a desiccator over silica gel.Data for H6L1 (I): Yield 0.954 g (85%). Anal. Calc. for C30H24N6O6(5 6 4): C, 63.83; H, 4.29; N, 14.89. Found: C, 65.31; H, 4.82; N,13.83%. IR data (cm1): 3440 (OAH), 3018 (NAH), 1659 (CO),1563 (CN). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol; for 24.0h;Reflux; | General procedure: The ligands H6L1-7 were prepared by similar methods. A representativemethod for I is presented here. A solution of salicylaldehyde(1.46 g, 12 mmol) in MeOH (30 mL) was added to amethanolic suspension of <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>(0.504 g, 2 mmol). The reaction mixture was refluxed on an oilbath. During this period, the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>slowly dissolved and simultaneously a white solid precipitated.After 24 h of reflux, the reaction mixture was cooled at room temperaturefor an hour, the precipitated solid was filtered, washedwith MeOH (2 5 mL) and dried in a desiccator over silica gel.Data for H6L1 (I): Yield 0.954 g (85%). Anal. Calc. for C30H24N6O6(5 6 4): C, 63.83; H, 4.29; N, 14.89. Found: C, 65.31; H, 4.82; N,13.83%. IR data (cm1): 3440 (OAH), 3018 (NAH), 1659 (CO),1563 (CN). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In methanol; for 24.0h;Reflux; | General procedure: The ligands H6L1-7 were prepared by similar methods. A representativemethod for I is presented here. A solution of salicylaldehyde(1.46 g, 12 mmol) in MeOH (30 mL) was added to amethanolic suspension of <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>(0.504 g, 2 mmol). The reaction mixture was refluxed on an oilbath. During this period, the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>slowly dissolved and simultaneously a white solid precipitated.After 24 h of reflux, the reaction mixture was cooled at room temperaturefor an hour, the precipitated solid was filtered, washedwith MeOH (2 5 mL) and dried in a desiccator over silica gel.Data for H6L1 (I): Yield 0.954 g (85%). Anal. Calc. for C30H24N6O6(5 6 4): C, 63.83; H, 4.29; N, 14.89. Found: C, 65.31; H, 4.82; N,13.83%. IR data (cm1): 3440 (OAH), 3018 (NAH), 1659 (CO),1563 (CN). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In methanol; for 24.0h;Reflux; | General procedure: The ligands H6L1-7 were prepared by similar methods. A representativemethod for I is presented here. A solution of salicylaldehyde(1.46 g, 12 mmol) in MeOH (30 mL) was added to amethanolic suspension of <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>(0.504 g, 2 mmol). The reaction mixture was refluxed on an oilbath. During this period, the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>slowly dissolved and simultaneously a white solid precipitated.After 24 h of reflux, the reaction mixture was cooled at room temperaturefor an hour, the precipitated solid was filtered, washedwith MeOH (2 5 mL) and dried in a desiccator over silica gel.Data for H6L1 (I): Yield 0.954 g (85%). Anal. Calc. for C30H24N6O6(5 6 4): C, 63.83; H, 4.29; N, 14.89. Found: C, 65.31; H, 4.82; N,13.83%. IR data (cm1): 3440 (OAH), 3018 (NAH), 1659 (CO),1563 (CN). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In methanol; for 24.0h;Reflux; | General procedure: The ligands H6L1-7 were prepared by similar methods. A representativemethod for I is presented here. A solution of salicylaldehyde(1.46 g, 12 mmol) in MeOH (30 mL) was added to amethanolic suspension of <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>(0.504 g, 2 mmol). The reaction mixture was refluxed on an oilbath. During this period, the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>slowly dissolved and simultaneously a white solid precipitated.After 24 h of reflux, the reaction mixture was cooled at room temperaturefor an hour, the precipitated solid was filtered, washedwith MeOH (2 5 mL) and dried in a desiccator over silica gel.Data for H6L1 (I): Yield 0.954 g (85%). Anal. Calc. for C30H24N6O6(5 6 4): C, 63.83; H, 4.29; N, 14.89. Found: C, 65.31; H, 4.82; N,13.83%. IR data (cm1): 3440 (OAH), 3018 (NAH), 1659 (CO),1563 (CN). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In N,N-dimethyl-formamide; at 90.0℃; for 8.0h; | (2) Add the above-mentioned trimesic hydrazide (5.0g, 0.02mol) and 3,4-dihydroxybenzaldehyde (8.21g, 0.06mol) into a 250mL flask containing 100mL DMF, magnetically at 90C The reaction was stirred for 8 hours, dispersed into a beaker containing a large amount of water while hot, filtered with suction and washed with ethanol three times, and dried under vacuum at 0.06MPa and below 60C to obtain a pure yellow powdery Zn2+ probe compound. The calculated yield was 96%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With hydrazine hydrate; acetic acid; In ethanol; dimethyl sulfoxide; at 80.0℃; for 24.0h; | Add 25ml of ethanol to a 50ml round bottom flask, 1,3,5-Benzenetrihydrazide (0.67g, 2.66mmol) is stirred and dissolved; Take another 250ml round bottom flask and add 50ml DMSO, 4-Diphenylaminobenzaldehyde (2.6g, 9.56mmol) is stirred and dissolved, After dissolving, add the trimellitic hydrazide solution to the 4-diphenylaminobenzaldehyde solution, Add 2 drops of glacial acetic acid, stir and reflux for 24h at 80C. After the reaction is completed, the reaction solution is cooled to room temperature, A large amount of solid precipitated and filtered under reduced pressure. The filter cake was washed 3 times with ethanol and dried, The pure target compound (1) N'1, N'3, N'5-tris((E)-4-(diphenylamino)benzylidene)<strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong> is obtained. Yield 83%, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In methanol; for 24.0h;Reflux; | These ligands were synthesized by a general procedure. Synthesis of H6L1 (I) is presented here. A methanolic (20 mL) suspension of the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong> (H3bthz) (0.252 g, 1 mmol) was added to 3-acetyl-2-hydroxy-6-methyl-4H-pyran-4-one (2.12 g, 3 mmol) dissolved in MeOH (70 mL) and the reaction mixture was heated at reflux inan oil bath along with slow magnetic stirring. The trihydrazide slowly went into solution in ca. 3 h. After ca. 24 h of reflux, a clear solution was cooled to room temperature where a pale yellow solid slowly precipitated. The solid was filtered, washed with methanol and dried under vacuum over silica gel. Data for H6L1 (I). Yield 1.68 g (79%). C33H30N6O12 (702.6): calcd C, 56.41; H, 4.30; N, 11.96. Found C, 56.0; H, 4.5; N 11.59%. HR-MS: 703.204. IR (cm-1): 3343 (O-H), 3200 (N-H), 1647 (C- -O), 1508(C- -N) cm 1. 1H NMR (400 MHz, DMSO-d6): δ = 16.18 (s, 3H N-H)), 8.67 (br, 3H, O-H), 6.30 (s, 3H, aryl), 5.91 (s, 3H, aryl), 2.29 (s, 9H, CH3 on aryl), 2.13 (s, 9H, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | In methanol; for 24.0h;Reflux; | General procedure: These ligands were synthesized by a general procedure. Synthesis of H6L1 (I) is presented here. A methanolic (20 mL) suspension of the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong> (H3bthz) (0.252 g, 1 mmol) was added to 3-acetyl-2-hydroxy-6-methyl-4H-pyran-4-one (2.12 g, 3 mmol) dissolved in MeOH (70 mL) and the reaction mixture was heated at reflux inan oil bath along with slow magnetic stirring. The trihydrazide slowly went into solution in ca. 3 h. After ca. 24 h of reflux, a clear solution was cooled to room temperature where a pale yellow solid slowly precipitated. The solid was filtered, washed with methanol and dried under vacuum over silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In methanol; for 24.0h;Reflux; | General procedure: These ligands were synthesized by a general procedure. Synthesis of H6L1 (I) is presented here. A methanolic (20 mL) suspension of the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong> (H3bthz) (0.252 g, 1 mmol) was added to 3-acetyl-2-hydroxy-6-methyl-4H-pyran-4-one (2.12 g, 3 mmol) dissolved in MeOH (70 mL) and the reaction mixture was heated at reflux inan oil bath along with slow magnetic stirring. The trihydrazide slowly went into solution in ca. 3 h. After ca. 24 h of reflux, a clear solution was cooled to room temperature where a pale yellow solid slowly precipitated. The solid was filtered, washed with methanol and dried under vacuum over silica gel. |