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CAS No. : | 14783-09-6 | MDL No. : | MFCD00134224 |
Formula : | C12H8Cl2CuN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PHECBGBJCLDCMF-UHFFFAOYSA-L |
M.W : | 314.66 | Pubchem ID : | 6100472 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
65% | In tetrahydrofuran; for 0.5h; | All commercially available reagents and chemicals were of reagent grade purity and used without further purification. Copper(II) chloride dihydrate and dimethylformamide were purchased from Sigma-Aldrich; copper(II) perchlorate hexahydrate, tetrahydrofuran, and 1,10-phenanthroline were purchased from Merck; and triethylamine, 1,3-benzenedicarboxylic acid (1,3-H2bdc) were purchased from Sigma-Aldrich. The precursor [Cu(phen)Cl2] was synthesized as follows: a solution (10 mL) of tetrahydrofuran containing CuCl2*2H2O (0.542 g, 3.2 mmol) was added slowly to a solution (10 mL) of THF containing 1,10-phenantroline (0.577 g, 3.2 mmol) under continuous stirring for 30 minutes. The desired precursor precipitated as a green powder, which was filtered, washed with THF, and air-dried. Yield 65%. Anal Calcd for C12H8Cl2CuN2 (314.66 g mol-1): C, 45.80; H, 2.56; N, 8.90; Cu, 20.20; Found: C, 45.29; H, 2.63; N, 8.67; Cu, 19.89. FTIR (νmax/cm-1): 3080, 3060, 3047 (CH); 1628, 1609, 1586, 1512, 1424 (CC/CN); 1351, 1317 (δCH); 1220 (CN), 1147 (δring + νCC); 1103, 1049 (δCH); 952 (νCC); 859, 777, 717 (γCH); 494 (νCu-N). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | In methanol; at 20℃; for 24.0h; | General procedure: The complexes were obtained by dissolving 0.31 mmolof the [CuCl2(phen)] in 50 mL of methanol together withgentle heating and stirring. After that 0.31 mmol of HL1 orHL2 was added. The mixture was stirred at room temperaturefor 24 h. The solution volume was reduced using a rotationalevaporator. The solids which precipitated were filtered andwashed with diethyl ether and dried in vacuum. [CuCl(L1)(phen)].0.5H2O (1)Green solid; yield: 44%; elemental analysis for(C23H18ClCuN4O4.5) calcd. (%): C 53.0, H 3.3, N 10.8;found (%): C 52.6, H 3.1, N 10.7; molar conductivity(1 × 10-3 mol L-1, DMF): 47 μS cm-1; IR (KBr) ν/ cm-11240 m ν(CO), 1582 s ν(C=N), 1516 m νas(NO2),1348 m νs(NO2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | In methanol; at 20℃; for 24.0h; | General procedure: The complexes were obtained by dissolving 0.31 mmolof the [CuCl2(phen)] in 50 mL of methanol together withgentle heating and stirring. After that 0.31 mmol of HL1 orHL2 was added. The mixture was stirred at room temperaturefor 24 h. The solution volume was reduced using a rotationalevaporator. The solids which precipitated were filtered andwashed with diethyl ether and dried in vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In ethanol; | An ethanol solution (4 ml) of copper (II) chloride (0.051 g,0.3 mmol) was added to ethanol solution (4 ml) of 1,10-phenanthroline (0.059 g, 0.3 mmol) with stirring. Immediately formed precipitate was filtered out, washed with ethanol and dried in air. Yield (0,07 g): 78%. Elemental analysis (%): Calc. for C12H10N2Cl2Cu: C, 45.8; H, 2.6; N, 8.9. Found: C, 44.4; H, 2.5; N, 8.6. |
70% | In chloroform; at 20℃; for 24.0h; | Phenanthroline complexes and the new curcumin complexes (1a-b)were prepared according to published methods [14,27], with slightmodifications. 1.5 equiv. of CuCl2 or PdCl2 was added to a solution of 1,10-phenanthroline in CHCl3 (50 mL). After stirring for 24 h at roomtemperature, the suspension was filtered and the solid was washed withCHCl3. Cu(phen)Cl2: Green powder, 70% yield, m.p. > 300 C. IR (KBr,max/cm 1): 3077, 3056 (C-H aliphatic/aromatic), 1624 (C- -C), 1585(C- -N), 428 (Cu-N). Pd(phen)Cl2: Yellow powder, 75% yield, m.p. >300 C. IR (KBr, max/cm 1): 3097, 3058 (C-H aliphatic/aromatic),1631. (C- -C), 1579. (C- -N), 436 (Pd-N). The 1H NMR results weresimilar for phenanthroline complexes (500 MHz, DMSO-d6): (ppm),9.35 (d, 2H), 8.99 (d, 2H) 8.26 (s, 2H), 8.01 (m, 2H). The experimentaldata are following those reported in the previous literature [28,29]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca.70% | at 20℃; | To a solution of 0.149. g (1 mmol) of L-methionine in 10 ml of water 0.314 g (1 mmol) of Cu(phen)Cl2 obtained by the procedure [12] was added. When the resulting solution was slowly evaporated at room temperature a mixture of dark green and dark blue crystals was formed. Needle crystals suitable for XRD analysis were obtained by slow recrystallization of these crystals from water. Yield ~70%. The complex is readily soluble in water, low alcohols, and dimethyl sulfoxide. IR spectrum (KBr), ν, cm-1: 3532.5 [νs(NH2)], 3300.1 [νs(NH2)], 1637.8 [νas(CO2)], 1586.4 [νs(CO2)], 1518.1 (C-N, phen), 1427.8, 1343.9 [νs(S-CH3)], 852.1 [δ(C-C, phen)], 721.3 [δ(C-N, phen)]. Electronic spectrum (H2O) λ, nm (ε, L mol-1 cm-1): 642 (45). Found, %: C 41.55; N 8.45; Cu 12.65. C17H26ClCuN3O5.5S. Calculated, %: C 41.63; N 8.57; Cu 12.84. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With triethylamine; In ethanol; water; at 20℃; for 0.166667h;Inert atmosphere; | General procedure: General method: To a solution of (N^N)MCl2 (0.591 mmol) in10 mL degassed H2O was added 20 mL degassed ethanol solutioncontaining quercetin (0.200 g, 0.591 mmol) and NEt3 (0.16 mL,1.182 mmol). The product formed instantly as a red precipitate inthe case of Cu(II) complexes and orange solid in the case of Zn(II)complexes and was filtrated out, washed repeatedly with waterand ethanol and dried under vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With triethylamine; In dichloromethane; for 0.5h; | General procedure: Lap (30mg) was added to a solution of [Cu(phen)Cl2] (20mg) in dichloromethane (10mL) in a ratio 2:1, in the presence of a stoichiometric amount of triethylamine to deprotonate the ligand. Immediately, the reaction solution turned red, and the reaction mixture was vigorously stirred for a half an hour. Then the precipitate was separated by filtration, and transferred to an ether atmosphere at low temperature for crystallization. Two days later single crystals of (1)·0.5CH2Cl2 suitable for X-ray crystallography were obtained. After isolation and drying in air, the complex lost all solvated molecules. Yield of 1 64%. Elemental analyses: Calculated % C: 66.50; % H 4.85; Found: 66.90 %; % H 4.70. IR νmax: 1643, 1587, 1538, 1344, 1269, 1427cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | For compound 2, 1,3-H2bdc (0.204 g, 1.0 mmol) and Et3N (1.3 mL, 9.3 mmol) were dissolved in 10 mL of water:ethanol (1:2) and added dropwise under continuous stirring to an aqueous solution (30 mL) of [Cu(phen)Cl2] (0.314g, 1.0 mmol) at 80C leading to the precipitation of a blue solid, which was filtered, dissolved in 5mL of DMF:water solution (1:1) and maintained at room temperature. Blue crystals suitable for single crystal X-ray diffraction analysis were obtained after 7 days. Yield 36%. Anal Calcd for C23H21CuN3O6 (498,97 g mol-1): C, 55.25; H, 4.38; N, 8.40; Cu, 12.71; Found: C, 55.12; H, 4.44; N, 8.41; Cu, 12.67. FTIR (νmax/cm-1): 3299 (OH); 3074, 3063, 2948, 2926 (CH); 1674 (CO); 1603, 1519, 1491, 1421 (CC/CN); 1554 (asCOO-); 1382, 1360 (sCOO-); 1257, 1218 (CO), 1152 (δring + νCC); 1081, 851 (γCH), 753, 720 (δCOO-); 595 (δring). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; | H 2 L (60 mg, 0.2 mmol) was added to 2 mL solution of [Cu(phen)Cl 2 ] (95 mg, 0.3 mmol) in DMF. The ligand dissolved quickly, and color of the reaction mixture immediately changed to dark green. The reaction mixture was kept at room temperature, and after several days, crystalline solid suitable for X-ray analysis deposited. The solid was filtered off, washed with small amount of MeOH and dried under vacuum. |