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CAS No. : | 630067-06-0 | MDL No. : | MFCD06255104 |
Formula : | C13H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UCJSMIWAXWPDOJ-UHFFFAOYSA-N |
M.W : | 224.21 | Pubchem ID : | 3446446 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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 |
---|---|---|
50% | In ethanol; water Ru complex and ligand (3 equiv.) in H2O-EtOH refluxed for 6.5 h; monitored by TLC; solvent stripped; dissolved in min. hot H2O; slowly dripped into satd. NaClO4 soln. with stirring; ppt. collected by suction filtration; purified by column chromy. (neutral alumina, MeCN to MeCN-MeOH); most copious fraction collected; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene Re complex and ligand (1.1 equiv.) in toluene refluxed for 2 h; recrystd. from MeOH; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water RuCl3*nH2O and ligand (5 equiv.) in H2O-EtOH refluxed for ca. 6 h; monitored by TLC; solvent stripped; triturated with MeOH; concd.; dripped into satd. NaClO4 soln.; ppt. collected; purified by column chromy. (neutral alumina, MeOH to MeOH-H2O); last fraction collected; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide RuCl3*nH2O and ligand (2 equiv.) in DMF stirred at reflux for 4.75 h; monitored by TLC; solvent stripped; small amt. of H2O added; ppt. isolatedbu suction filtration; washed (H2O, acetone); mixed with KCN in H2O; re fluxed for 6.5 h; solvent stripped; triturated with MeOH; sepd. by column chromy. (neutralalumina, MeOH to MeOH-H2O); most copious fraction collected; elem. anal .; three isomers obtained; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water Ru complex and ligand (2 equiv.) in H2O-EtOH refluxed for ca. 4-6 h; monitored by TLC; solvent vol. reduced; dripped into stirred satd. NaClO4 soln.; ppt. collected by suction filtration; washed with cold H2O; dried; purified by column chromy. (neutral alumina, acetone, acetone-MeOH, MeOH, MeOH-H2O); last band collected; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene 2: AgClO4*H2O / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene 2: tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With nitronium tetrafluoborate; silver carbonate In N,N-dimethyl acetamide at 90℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In dichloromethane Stage #2: 1,10-phenanthroline-5-carboxylic acid With dicyclohexyl-carbodiimide In dichloromethane at 48℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane at 0℃; for 25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1,10-phenanthroline-5-carboxylic acid With benzotriazol-1-ol; diisopropyl-carbodiimide In dimethyl sulfoxide; N,N-dimethyl-formamide for 0.166667h; Stage #2: C39H54N7O11Pol In dimethyl sulfoxide; N,N-dimethyl-formamide Stage #3: With chlorotriisopropylsilane; trifluoroacetic acid In water for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1,10-phenanthroline-5-carboxylic acid With benzotriazol-1-ol; diisopropyl-carbodiimide In dimethyl sulfoxide; N,N-dimethyl-formamide for 0.166667h; Stage #2: C31H59N10O7Pol In dimethyl sulfoxide; N,N-dimethyl-formamide Stage #3: With chlorotriisopropylsilane; trifluoroacetic acid In water for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1,10-phenanthroline-5-carboxylic acid With benzotriazol-1-ol; diisopropyl-carbodiimide In dimethyl sulfoxide; N,N-dimethyl-formamide for 0.166667h; Stage #2: C51H95N20O7Pol In dimethyl sulfoxide; N,N-dimethyl-formamide Stage #3: With chlorotriisopropylsilane; trifluoroacetic acid In water for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1,10-phenanthroline-5-carboxylic acid With benzotriazol-1-ol; diisopropyl-carbodiimide In dimethyl sulfoxide; N,N-dimethyl-formamide for 0.166667h; Stage #2: C52H91N24O13Pol In dimethyl sulfoxide; N,N-dimethyl-formamide Stage #3: With chlorotriisopropylsilane; trifluoroacetic acid In water for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: bis[μ-chloro-bis(2-phenylisoquinolinato-C2,N)iridium(III)]; 1,10-phenanthroline-5-carboxylic acid In methanol; dichloromethane at 20℃; for 10h; Stage #2: ammonium hexafluorophosphate In methanol; dichloromethane for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: [iridium(III)(μ-chloro)(2-phenylpyridine)2]2; 1,10-phenanthroline-5-carboxylic acid In methanol; dichloromethane at 20℃; for 10h; Stage #2: ammonium hexafluorophosphate In methanol; dichloromethane for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In ethanol Reflux; | 3.3. Preparation of Re(5-COOH-phen)(CO)3Cl (4) Re(CO)5Cl (0.26 g, 0.72 mmol) and 5-COOH-phen (0.16 g, 0.72 mmol) were added along with 25 mL ethanol and a magneticstir bar to a 100 mL round-bottom flask. The solution was refluxedovernight during which time the solution turned yellow-orange. Atthe end of the reaction, a dark orange precipitate was present. Theprecipitate was collected by vacuum filtration on a fine-frit glassfunnel.Color: Yellow, 84.0% yield. Anal. Calcd. for ReC16H8O5N2Cl: C,36.27; H, 1.52; N, 5.29. Found. C, 34.65; H, 1.50; N, 5.02. IR (KBrpellet, cm1): (CO) 3300 (broad), 2014 sh,1907 sh, 1H NMR (DMSO):d ppm 8.14 (dd, 1H, J 5.2, 2.4 Hz), 8.18 (dd, 1H, J 5.2, 2.4 Hz), 9.04(s, 1H), 9.02 (dd, 1H, J 8.4, 1.6 Hz), 9.50 (m, 2H), 9.70 (dd, 1H,J 8.8, 1.2 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In water Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; diisopropyl-carbodiimide In dimethyl sulfoxide; N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Stage #1: 1,10-phenanthroline-5-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-(2-AMINOETHYL)MORPHOLINE In N,N-dimethyl-formamide for 72h; Inert atmosphere; | Synthesis of ligand N-(2-morpholinoethyl)-1,10-phenanthroline-5-carboxamide(ligand PhAEM) 1,10-Phenanthroline-5-carboxylic acid (1 equiv.; 0.89 mmol)was solubilized in 5 mL of DMF with HATU (1.2 equiv.,1.07 mmol) and DIPEA (3 equiv., 2.67 mmol), and themixture was stirred for 1 h at room temperature until thesolution turned dark brown. 4-(2-Aminoethyl)morpholine(1.2 equiv., 1.07 mmol) was then added to the reaction andstirred overnight. DMF was evaporated under vacuum andthe residue washed with 100 mL H2O.The white residuewas filtered through a glass wool plug with cold Et2O,andvacuum-dried to afford the desired product with 72% yield.1H NMR (400 MHz, DMSO-d6): δ (ppm) 9.18-9.15 (Hab,dd; 2H), 9.06-9.03 (NH, t, 1H), 8.81-8.78 (Hd, dd, 1H),8.60-8.58 (Hc, dd, 1H), 8.22 (He, s, 1H), 7.89-7.82 (Hfg,mult, 2H), 3.78-3.73 (O-CH2, mult, 4H), 8H morpholine inHDO d 13C NMR (101 MHz, DMSO-D6): δ (ppm) 167.69,151.21, 150.15, 145.45, 137.14, 134.67, 132.20, 126.93,126.51, 125.67, 124.09, 123.50, 63.58, 55.27, 51.57, 34.12.IR (cm-1): 3414, 1654-1651, 1548 ESI-MS (positive mode)for C19H20N4O2[M-H]+, calculated 337.1659 m/z; found337.1661 [M-H]+ (0.52 ppm). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | Stage #1: 1,10-phenanthroline-5-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 6-N-Biotinylaminohexanol In N,N-dimethyl-formamide | Synthesis of 1,10-phenanthroline-5-hexanoate-biotinamide(ligand PhBio) 1,10-Phenanthroline-5-carboxylic acid (1 equiv.; 0.30 mmol)was solubilized in 5 mL of DMF with HBTU (1.2 equiv.,0.35 mmol) and DIPEA (3 equiv., 0.90 mmol) and the mixturestirred for 1 h at room temperature until the solutionturned dark brown. N-(Hexanol)biotinamide (1.2 equiv.,0.35 mmol) was then added to the reaction and stirred overnight.DMF was evaporated under vacuum and the residuewashed with 100 mL H2O.The white residue was filteredthrough a glass wool plug with cold Et2O,and vacuumdriedto afford the desired product in 52% yield. 1H NMR(400 MHz, DMSO-d6): δ (ppm) 9.23-9.22 (Ha, d; 1H,J = 1.8 Hz), 9.21-9.20 (Hb, d, 1H, J = 1.9 Hz), 9.16-9.15(Hd, dd, 1H, J1 = 1.8 Hz, J2 = 4.3 Hz), 8.72-8.69 (Hc, dd,1H, J1 = 1.8 Hz, J2 = 8 Hz), 8.70 (He, s, 1H, J = 1.5 Hz),7.87-7.83 (Hfg, mult, 2H), 7.76-7.73 (NH, t, 1H,J = 5.9 Hz), 6.40 (NH, s, 1H), 6.34 (NH, s, 1H) 4.44-4.41(Hh, t, 2H, J = 6.6 Hz), 4.29-4.26 (Hm, mult, 1H), 4.11-4.08(Hn, mult, 1H), 3.09-3.01 (Hki, massif, 3H), 2.80-2.76 (Hl,dd, 1H, J1 = 7.4 Hz, J2 = 13.8 Hz), 2.55-2.53 (Hl, d, 1H,J = 11.2 Hz), 2.05-2.01 (Hj, t, 2H, J = 7.4 Hz), 1.84-1.77(Hi, quint, 2H, J = 7.1 Hz), 1.63-1.21 (H aliphatic, massif,14H), 13C NMR (101 MHz, DMSO-d6): δ (ppm) 172.37,166.38, 163.22, 152.84, 150.70, 147.32, 146.13, 138.29,134.57, 132.21, 127.10, 126.29, 126.19, 124.52, 124.23,65.90, 61.57, 59.71, 55.96, 38.74, 35.76, 29.56, 28.74,28.67, 28.57, 26.58, 25.87, 25.74. IR (cm-1): 3300, 3205,2936, 2855, 1731, 1674, 1634. ESI-MS (positive mode)for C29H35N5O4S[M-H]+, calculated m/z 550.2483; found550.2482 [M-H]+ (0.05 ppm). |
Tags: 630067-06-0 synthesis path| 630067-06-0 SDS| 630067-06-0 COA| 630067-06-0 purity| 630067-06-0 application| 630067-06-0 NMR| 630067-06-0 COA| 630067-06-0 structure
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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