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CAS No. : | 94-93-9 | MDL No. : | MFCD00002244 |
Formula : | C16H16N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VEUMANXWQDHAJV-UHFFFAOYSA-N |
M.W : | 268.31 | Pubchem ID : | 26518 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 81.73 |
TPSA : | 65.18 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.47 cm/s |
Log Po/w (iLOGP) : | 2.41 |
Log Po/w (XLOGP3) : | 2.06 |
Log Po/w (WLOGP) : | 2.64 |
Log Po/w (MLOGP) : | 1.57 |
Log Po/w (SILICOS-IT) : | 3.98 |
Consensus Log Po/w : | 2.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.92 |
Solubility : | 0.326 mg/ml ; 0.00122 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.06 |
Solubility : | 0.235 mg/ml ; 0.000876 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.76 |
Solubility : | 0.00465 mg/ml ; 0.0000173 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.5 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-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 |
---|---|---|
90% | at 20℃; for 1 h; | c) Synthesis of VO(salen) catalyst; Step 1 : salen; Salicaldehyde (7.307 g, 6.38 ml, 0. 0598 mol) and ethylene diamine (1. 798 g, 2 ml, 0.0299 mol) were combined in absolute EtOH and stirred for 1 hour at room temperature. The resulting precipitate was filtered, washed with EtOH and air dried. Yield: 7.25 g (90percent). |
88% | Reflux | General procedure: The Schiff bases used for the synthesis of the catalysts were prepared by the well known reaction between salicylaldehyde and diamine. Slight experimental variations were introduced with respect to literature methods [27] and the resulting procedure was successfully applied to a number of differently substituted aldehydes. (0015) General procedure: Two equivalents of the appropriate salicylaldehyde were dissolved in the minimum volume of boiling methanol (generally, 20 ml) and added dropwise with one equivalent of diamine (either 1,2-diaminoethane or 1,2-benzenediamine) in 5 ml methanol. The solution was refluxed until all the aldehyde disappeared (TLC analysis) and then cooled to room temperature, thus causing precipitation of the Schiff base, as a yellow solid. The filtered solid was washed with a small amount of methanol, then with diethyl ether and dried. The following Schiff bases were prepared: (0016) Salophen, [1,2-bis-(salicylideneamino)benzene]: yield 95.3percent; 5,5′-Cl2salophen, [1,2-bis-(5-Cl-salicylideneamino)benzene]: yield >99percent; 5,5′-(t-Bu)2salophen [1,2-bis-(5-t-Bu-salicylideneamino)benzene]: yield 75percent; 3,3′-(OMe)2salophen, [1,2-bis-(3-OMe-salicylideneamino)-benzene]: yield 77percent; 5,5′-(OMe)2salophen, [1,2-bis-(5-OMe-salicylideneamino)-benzene]: yield 79percent; 3,3′,5,5′-Cl4salophen [1,2-bis-(3,5-Cl2salicylideneamino)benzene]: yield 95percent; 3,3′,5,5′-(t-Bu)4salophen [1,2-bis-(3,5-di-t-Bu-salicylideneamino)benzene]: yield 75percent. (0017) Salen, [1,2-bis-(salicylideneamino)ethane]: yield 88percent; 5,5′-Cl2salen, [1,2-bis-(5-Cl-salicylideneamino)ethane]: yield 67percent; 5,5′-(t-Bu)2salen, [1,2-bis-(5-t-Bu-salicylideneamino)ethane]: yield 91percent; 3,3′-(OMe)2salen, [1,2-bis-(3-methoxy-salicylideneamino)ethane]: yield 92percent; 5,5′-(OMe)2salen, [1,2-bis-(5-OMe-salicylideneamino)ethane]: yield 92percent; 3,3′,5,5′-Cl4salen, [1,2-bis-(3,5-Cl2-salicylideneamino)ethane]: yield 70percent; 3,3′,5,5′-(t-Bu)4salen, [1,2-bis-(3,5-(t-Bu)2-salicylideneamino)ethane]: yield 72percent. (0018) All the compounds gave 1H NMR and UV–vis spectra consistent with the structure and with literature data [25,28–30]. |
79% | With polymer supported zinc(II)-salen complex In water at 80℃; for 2 h; Green chemistry | General procedure: Varying the procedure from the literature, 10 mg catalyst was added to a solution of ethylenediamine (1 mmol, 60 mg) and 2 mmol of benzaldehyde derivative in 10 mL distilled water and refluxed at 80 °C for 2 h. The reaction mixture was poured onto ice, and the resulting precipitate was dissolved in ethyl acetate and the catalyst was separated by filtration. Evaporate off EtOAc to get Schiff bases, which can be further recrystallized using ethanol. (4a) 2,2’-((1E,1’E)-(Ethane-1,2-diylbis(azanylylidene))bis (methanylylidene))diphenol (Yield = 79percent); 1H NMR (400 MHz, CDCl3) δ = 13.19 (s, 2H), 8.35 (s, 2H), 7.30-7.21 (m, 4H), 6.94 (d, J = 8.35 Hz, 2H), 6.8 (t, J = 7.75 Hz, 2H), 3.93 (S, 4H). 13C NMR (100 MHz, CDCl3) 166.52, 161.02, 132.41, 131.50, 118.69, 118.65, 116.97, 59.77. GC-MS m/z: calcd. for C16H16N2O2: 268.1212 and found 268.2494. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.9% | With ethylenediamine In ethanol | Catalytic Disproportionation of Hydrogen Peroxide EXAMPLE 41 Preparation of: STR78 A solution of salicylaldehyde (24.42 g, 0.200 molc) in 80 ml of EtOh was added to a stirred solution of ethylenediamine (6.070 g, 0.100, olc) in a mixture of 50 ml EtOH and 50 ml of H2 O over a period of 5 minutes. The reaction mixture was refluxed for 1 hour and stirred at room temperature overnight. The yellow crystalline product was separated by filtration and washed with 2*30 ml of cold 60percent EtOh and air dried to yield 25.733 g (95.9percent) of salen. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With sodium tetrahydroborate; In methanol; at 30℃; for 0.5h; | General procedure: Sodium borohydride (2.0 equiv) was added to a stirring suspension of the imino-compound (1A-6A) (1.0 equiv) in methanol (20 mL) at room temperature. After 30 min the reaction mixture was poured on ice and the resulting suspension filtered. The obtained solid was washed with water and n-hexane to give the corresponding amino-derivate (1B-6B) in high yields. Some compounds have been already synthesized and characterized and our results (Supplementary data) are in complete agreement with those reported in the literature. |
70% | With sodium tetrahydroborate; In N,N-dimethyl-formamide; | The ethylenediamine (0.003 mol), dissolved in 20 cm3 ofmethanol, was added dropwise to salysilaldehyde (1) (0.003 mol) in 150 cm3 of methanol. After the addition, the reaction mixture was stirred to room temperature, and 0.006 mol of sodium borohydride in 15 mL of dimethylformamide was added in portions with stirring. The yellow colour of the reaction mixture disappears with addition of all portion of sodium borohydride, indicated to completionof hydrogenation. When the reduction was completed,mixture was poured in cold distilled water. Formed white precipitate was washed with water and diethyl ether, andthen dried over anhydrous sodium sulphate. |
With methanol; sodium tetrahydroborate; for 0.25h;Reflux; | General procedure: General procedure for synthesis of BC-1209. 2-Hydroxybenzaldehyde (0.01 mol, 1.22 g) were added to a solution of ethylenediamine (0.005 mol, -350 ul) in anhydrous ethanol (20 ml). The resulting solution was heated and stirred for 10 min until the precipitation of the relevant Schiff base. The Schiff bases were filtered off, and washed with cold ethanol. The Schiff base was then added to 30 ml absolute methanol. A 10% solution of sodium borohydride (0.02 mol) was dissolved in absolute methanol and added to the Schiff base. When the dropwise addition of sodium borohydride was complete, the reaction solution was refluxed for an additional 15 min. Solvent was then removed through rotary evaporation and 40 ml cold water was added to liberate the secondary amine. The precipitation of BC-1209 were collected, washed with water and dried, followed by recrystallization from ethyl acetate. |
With sodium tetrahydroborate; In methanol; at 20℃; for 2h; | General procedure: Schiff base ligand can be easily converted to tetrahydro-Schiff base ligand by the hydrogenation ofCH=N to CH2-NH in presence of NaBH4 in MeOH.Tetrahydro-Schiff base ligands were prepared as follows:0.01 mol of SalenH2, SalhexenH2 or SalphenH2was dissolved in 60 mL of methanol, followed by theaddition of 0.011 mol of NaBH4 at ambient temperature.After stirring for 2 h, the solvent was removedunder reduced pressure. The solid product was furtherwashed with distilled water and recrystallized fromethanol, and the obtained materials were denoted as[H4]SalenH2, [H4]SalhexenH2 and [H4]SalphenH2,respectively. The 1H NMR spectra of [H4]SalenH2,[H4]SalhexenH2 and [H4]SalphenH2 are also shown inFig. 1. 1H NMR (CDCl3), δ, ppm: [H4]SalenH2 -7.25-6.78 (8H, m, Ar-H), 3.99 (4H, s, N-CH2CH2-N), 2.84 (4H, s, CH2-NH) (Fig. 1b); | |
With hydrogenchloride; sodium tetrahydroborate; In methanol; water; | The di-Schiff base ligand from 1,3-propanediamine and salicylaldehydewas synthesized by a reported method [17]. 5 mmol of1,3-propanediamine (0.42 mL) was mixed with 10 mmol of the salicylaldehyde(1.04 mL) in methanol (30 mL). The resulting solutionwas refluxed for ca. 2 h and allowed to cool. Then 30 mL (5 mmol)of this prepared yellow methanolic ligand solution (H2L1) wascooled to 0 C, and solid sodium borohydride (570 mg, 15 mmol)was added to this methanol solution with stirring. After completionof addition, the resulting solution was acidified with concentratedHCl (12 mL) and then evaporated to dryness [18]. Thereduced Schiff base ligand H2L1R was extracted from the solid masswith methanol, and this colorless methanol solution (ca. 30 mL)was added to a methanolic solution (10 mL) of Cu(ClO4)26H2O(1.852 g, 5 mmol) to prepare the ‘‘metalloligand” [CuL1R] | |
With hydrogen; In methanol; at 25℃; under 1520.1 Torr; for 24h; | First, 100 mL of methanol in which 3.5 × 10 -1 mmol of Compound II was dissolved was placed in a round bottom flask 101. Next, while supplying H 2 from the hydrogen cylinder of the hydrogen supply apparatus to the hydrogen supply module 1 at 2 atm, the mixture was stirred for 24 hours in an environment at an indoor temperature of 25 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In ethanol; at 70℃; for 2h; | General procedure: A solution of aldehyde derivative (4 mmol) and 1, 2-diamine derivative 1a-1c (2.0 mmol) in EtOH (8 mL) maintained for 2 h at 700C under stirring. Reaction completion monitored with TLC. Reaction mass cooled to room temperature and the solid obtained was filtered and dried. 2,2?-{ethane-1,2-diylbis[azanylylidene(E) methany lylidene]diphenol [SB01] m.p.: 125-1270C; Colour: Yellow; EIMS [M+2]: 269.23; FTIR(KBr cm-1): 3025, 2940, 2906, 2873, 2738, 1635, 1477, 1361, 1276, 1186, 1033, 827, 777, 628; 1H-NMR (300 MHz, DMSO-d6) delta: 3.895 (s, 2H), 6.825-6.884 (m, 4H), 7.271-7.409 (m, 4H), 8.565 (m, 4H) 13.358 (s, 2H); Elemental analysis [C16H16N2O2]: observed (Calculated): C 71.92% (71.62%), H 5.87% (6.01%), N 10.76% (10.44%). |
90% | In ethanol; at 20℃; for 1h; | c) Synthesis of VO(salen) catalyst; Step 1 : salen; Salicaldehyde (7.307 g, 6.38 ml, 0. 0598 mol) and ethylene diamine (1. 798 g, 2 ml, 0.0299 mol) were combined in absolute EtOH and stirred for 1 hour at room temperature. The resulting precipitate was filtered, washed with EtOH and air dried. Yield: 7.25 g (90%). |
88% | In methanol;Reflux; | General procedure: The Schiff bases used for the synthesis of the catalysts were prepared by the well known reaction between salicylaldehyde and diamine. Slight experimental variations were introduced with respect to literature methods [27] and the resulting procedure was successfully applied to a number of differently substituted aldehydes. (0015) General procedure: Two equivalents of the appropriate salicylaldehyde were dissolved in the minimum volume of boiling methanol (generally, 20 ml) and added dropwise with one equivalent of diamine (either 1,2-diaminoethane or 1,2-benzenediamine) in 5 ml methanol. The solution was refluxed until all the aldehyde disappeared (TLC analysis) and then cooled to room temperature, thus causing precipitation of the Schiff base, as a yellow solid. The filtered solid was washed with a small amount of methanol, then with diethyl ether and dried. The following Schiff bases were prepared: (0016) Salophen, [1,2-bis-(salicylideneamino)benzene]: yield 95.3%; 5,5?-Cl2salophen, [1,2-bis-(5-Cl-salicylideneamino)benzene]: yield >99%; 5,5?-(t-Bu)2salophen [1,2-bis-(5-t-Bu-salicylideneamino)benzene]: yield 75%; 3,3?-(OMe)2salophen, [1,2-bis-(3-OMe-salicylideneamino)-benzene]: yield 77%; 5,5?-(OMe)2salophen, [1,2-bis-(5-OMe-salicylideneamino)-benzene]: yield 79%; 3,3?,5,5?-Cl4salophen [1,2-bis-(3,5-Cl2salicylideneamino)benzene]: yield 95%; 3,3?,5,5?-(t-Bu)4salophen [1,2-bis-(3,5-di-t-Bu-salicylideneamino)benzene]: yield 75%. (0017) Salen, [1,2-bis-(salicylideneamino)ethane]: yield 88%; 5,5?-Cl2salen, [1,2-bis-(5-Cl-salicylideneamino)ethane]: yield 67%; 5,5?-(t-Bu)2salen, [1,2-bis-(5-t-Bu-salicylideneamino)ethane]: yield 91%; 3,3?-(OMe)2salen, [1,2-bis-(3-methoxy-salicylideneamino)ethane]: yield 92%; 5,5?-(OMe)2salen, [1,2-bis-(5-OMe-salicylideneamino)ethane]: yield 92%; 3,3?,5,5?-Cl4salen, [1,2-bis-(3,5-Cl2-salicylideneamino)ethane]: yield 70%; 3,3?,5,5?-(t-Bu)4salen, [1,2-bis-(3,5-(t-Bu)2-salicylideneamino)ethane]: yield 72%. (0018) All the compounds gave 1H NMR and UV-vis spectra consistent with the structure and with literature data [25,28-30]. |
79% | With polymer supported zinc(II)-salen complex; In water; at 80℃; for 2h;Green chemistry; | General procedure: Varying the procedure from the literature, 10 mg catalyst was added to a solution of ethylenediamine (1 mmol, 60 mg) and 2 mmol of benzaldehyde derivative in 10 mL distilled water and refluxed at 80 C for 2 h. The reaction mixture was poured onto ice, and the resulting precipitate was dissolved in ethyl acetate and the catalyst was separated by filtration. Evaporate off EtOAc to get Schiff bases, which can be further recrystallized using ethanol. (4a) 2,2?-((1E,1?E)-(Ethane-1,2-diylbis(azanylylidene))bis (methanylylidene))diphenol (Yield = 79%); 1H NMR (400 MHz, CDCl3) delta = 13.19 (s, 2H), 8.35 (s, 2H), 7.30-7.21 (m, 4H), 6.94 (d, J = 8.35 Hz, 2H), 6.8 (t, J = 7.75 Hz, 2H), 3.93 (S, 4H). 13C NMR (100 MHz, CDCl3) 166.52, 161.02, 132.41, 131.50, 118.69, 118.65, 116.97, 59.77. GC-MS m/z: calcd. for C16H16N2O2: 268.1212 and found 268.2494. |
In methanol; at 50℃; for 3h;Autoclave;Product distribution / selectivity; | Following the general procedure described above in Example 5, ethylenediamine (6.0 g, 0.1 mol), salicylaldehyde (24.4 g, 0.2 mol) and methanol (120 ml) were added to an autoclave. The reaction mixture was heated at 50C for 3 h. The reaction progress was monitored by means of TLC analysis with ethanol:chloroform (9:2) developing system. When the completion of the reaction was confirmed the sample of a salen compound was isolated to perform the 1H NMR analysis and confirm the structure of the product obtained. 1H NMR (CDCl3) delta: 13.2 (s, 2H, OH), 8.35 (s, 2H, ArCHN), 7.32-6.83 (m, 8H, ArH), 3.93 (s, 4H, NCH2CH2). | |
In water; at 45℃; for 5h;Autoclave;Product distribution / selectivity; | Following the general procedure described in Example 5 ethylenediamine (6 g, 0.1 mol), salicylaldehyde (24.4 g, 0.2 mol) and water (100 ml) were added to the autoclave. The reaction mixture was heated at 45C for 5 h. The reaction progress was monitored by means of TLC analysis with ethanol:chloroform (9:2) developing system. When the completion of the reaction was confirmed the sample of a product was isolated to perform the 1H NMR analysis and confirm the structure of the obtained salen product (analysis consistent with the data presented in Example 6). | |
In ethanol; for 2h;Reflux; | General procedure: The bis-salicyldimine Schiff base ligands: H2-salen [N,N?bis (salicylidene)-ethylenediamine], H2-salpr [N,N?-bis (salicylidene)-propylenediamine] and H2-salph [N,N?-bis (salicylidene)-o-phenylenediamine] were prepared as follows [11,12]. (0006) A solution of salicyladehyde was added drop wise onto a solution of the amine in 50 ml ethanol in molar ratio of 1:1 or 1:2 for a period of 1 h. The reaction mixture was refluxed for 1 h with continuous stirring. The reaction was left to cool where coloured compounds were filtrated off and washed several times with water and ethanol and dried in vacuum desiccator over P4O10. The melting point of H2-salen, H2-salpr, H2-salph are 120 C, 65 C and 165 C. The elemental analysis and some of physical properties of the compounds are given in Table 1. A general skeleton I, II and III of the prepared compounds are given as follows: | |
In methanol; for 2h;Reflux; | General procedure: A solution of substituted salicylaldehyde (10 mmol) in methanol(20 mL) was added dropwise to a solution of different substituted 1,2-diaminoethane (5 mmol) in methanol (20 mL). The mixture was refluxedfor 2 h and the precipitate of Schiff base ligand was obtained assolid product. Then the solid was separated by filtration, washed withcold methanol and dried in vacuum. Finally, it was recrystallized frommethanol to yield as pure ligand. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Synthesis of N,N'-bis(salicylidene)ethylenediamine To a stirred solution of salicylaldehyde (12.21 g/10.62 mL) in 70 C. ethanol (100 mL) was added ethylenediamine (3.01 g/3.33 mL). A yellow crystalline material immediately formed, and the reaction mixture was allowed to cool to room temperature with stirring. The solution was filtered, and the crystals were washed with cold ethanol. The ethanol layers were combined and reduced to approximately 20 mL and allowed to stand at 0 C. overnight. The resulting crystals were collected by vacuum filtration and washed with water. The collected solids were dried in vacuo to obtain 13.15 g (98%) N,N'-bis(salicylidene)ethylenediamine as yellow platelets with a melting point of 126 C. (literature value (24) 127-128 C.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; sodium tetrahydroborate; potassium hydroxide; In dichloromethane; at 0℃; | General procedure: The Schiff base (2.27 mmol) dissolved in dichloromethane (10 mL). Reaction mass cooled at 00C and 2-3 drops of conc. KOH solution added. The solution of NaBH4 (2.0 mmol) in methanol added dropwise. Reaction mass stirred for 4-5 h until the yellow colour disappeared. Reaction monitored on TLC. After completion of reaction solvent distilled and cold water (10 mL) added to dissolve residue. pH adjusted to 4-5 by addition of dilute HCl. The white solid filtered, washed with water dried. 2, 2?-[ethane-1, 2-diylbis(azanediyl methylene)]diphenol [RSB01]m.p.: 1180C; Colour: white; MS [M+2]: 273.99; FTIR(KBr cm-1): 3490, 3463, 3363, 3052, 2942, 2852, 2593, 1602, 1479, 1417, 1353, 1268, 1189, 1126, 1074, 960, 815, 757, 626; 1H NMR (300 MHz, DMSO-d6) delta: 2.481 (m, 4H), 3.770 (s, 4H), 5.031 (s, 2H), 6.658-6.686 (m, 4H), 7.01-7.06 (m, 4H), 13.335 (s, 2H); Elemental analysis [C16H20N2O2]: observed (Calculated): C 70.63% (70.56%), H 7.31% (7.40%), N 10.34% (10.29%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With bis(acetylacetonate)oxovanadium; In methanol; for 1h;Heating / reflux; | Step 2: VO (salen); Salen (0.950 g, 3.54 mmol) and VO (acac) 2 (0.939 g, 3.54 mmol) were combined in absolute MeOH and the mixture refluxed for 1 hour. After cooling to room temperature the dark green crystalline product was collected by filtration, washed with MeOH and air dried. Yield: 1. 025 g, (87%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol;Heating / reflux; | The following compounds were prepared from Co(II) acetate and a stoichiometric amount of SALEN ligand in boiling methanol: Cobalt(II)-N,N'-bis(salicylidene)ethylenediamino Cobalt (II)-bis (N-salicylidene-aniline) Cobalt(II)-N,N'-bis(salicylidene)-1,6-propanediamine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25.733 g (95.9%) | With ethylenediamine; In ethanol; | Catalytic Disproportionation of Hydrogen Peroxide EXAMPLE 41 Preparation of: STR78 A solution of salicylaldehyde (24.42 g, 0.200 molc) in 80 ml of EtOh was added to a stirred solution of ethylenediamine (6.070 g, 0.100, olc) in a mixture of 50 ml EtOH and 50 ml of H2 O over a period of 5 minutes. The reaction mixture was refluxed for 1 hour and stirred at room temperature overnight. The yellow crystalline product was separated by filtration and washed with 2*30 ml of cold 60% EtOh and air dried to yield 25.733 g (95.9%) of salen. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate; In tetrahydrofuran; water; at 20℃; for 18h; | Ni(II)(salen) was prepared as follows. To a 500 mL round bottom flask was added 2.2196 g (8.2822 mmol) of salen (N,N'-disalicylideneethylenediamine) that was partially dissolved in 200 mL of a 1 : 1 solution of THF and water to give a yellow suspension. To this mixture was added 2 equivalents Of K2CO3 (2.2297 g, 16.133 mmol) and 1 equivalent of Ni?(OAc)2 4H2O (2.0516 g, 8.2440 mmol) simultaneously. The reaction was stirred for 18 hours at room temperature and pressure as the solution color changed from yellow to dark EPO <DP n="10"/>orange. The solid product was filtered using a 60 mL fine frit and washed with diethyl ether and then water until the filtrate became clear. The solid was dried under vacuum overnight. The yield of the complex was 2.4108 g (90%). 1H NMR: (CDCl35 ppm) delta. = 3.44 (s, 4H, CH2CH2); 6.52 - 6.56 (m, 2H5 salicyl phenyl); 7.03 - 7.05 (d, 2H, salicyl phenyl); 7.06 - 7.09 (dd, 2H, salicyl phenyl); 7.19 - 7.62 (m, 2H, salicyl phenyl); 7.51 (s, 2H, - NCJJ(Ph)). lambdamax/nm: (DMSO) (epsilon, M"1 cm"1) 390 (4233), 408 (6573), 440 (3390), 540 (121), see also Freire C. and Castro B., Spectroscopic characterisation of electrogenerated nickel(III) species. Complexes with N2O2 Schiff-base ligands derived from salicylaldehyde., J. Chem. Soc, Dalton Trans., 1491-1498 (1998); (suspension in phosphate buffer solution) 250, 323, 389. IR: (ICBr, cm"1) 469 (Ni-N), 411 (Ni-O), see Garg B.S. and Nandan Kumar D., Spectral studies of complexes of nickel(II) with tetradentate schiff bases having N2O2 donor groups, Spectrochimica Acta Part A, 59, No. 2, 229-234(6) (15 January 2003). ELEMENTAL ANALYSIS: Theoretical (%) C 59.13, H 4.34, N 8.62, Ni 18.06. Experimental (%) C 58.93, H 4.35, N 8.44, Ni 17.12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Then to the autoclave 0.2 g of the Pd/C was introduced, the air was removed and the reaction was carried out at 50C in the atmosphere of hydrogen gas under the pressure 5 atm for 3 h. When hydrogen absorption ceased the mixture of glyoxylic acid monohydrate (27.6 g, 0.3 mol) and triethylamine (40.4 g, 0.4 mol) in methanol (100 ml) was introduced to the salan compound. The reaction system was heated to 50C and hydrogen was introduced under the pressure of 10 atm. The reductive amination was carried out for 15 h, then the catalyst was filtered and the solvent evaporated by means of a rotary vacuum evaporator. The solid (62 g) obtained was dissolved in water and acidified with 10% hydrochloric acid to pH=2.0. Crystallization was carried out for 12 h at 8C. 37 g of the product N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid monohydrochloride trihydrate was separated with the overall yield 78% with respect to the starting ethylenediamine. The raw product was recrystallized form 85% ethanol. The structure of the product was confirmed by means of 1H NMR and the purity thereof by means of elemental analysis. 1H NMR (DMSO) delta: 7.23-6.78 (m, 8H, ArH), 4.06 (s, 4H, HOOCCH2N), 3.65 (s, 4H, ArCH2N), 3.22 (s, 4H, NCH2CH2) Elemental analysis: Calculated for C20H24N2O6· HCl · 3H2O: C 50.16, H 6.52, N 5.85, Found: C 50.15, H 6.58, N 5.81 | ||
Then to the autoclave 0.1 g of the Pd/C was introduced, the air was removed, the autoclave was pressurized with hydrogen and the reaction was carried out at 45-50C under the hydrogen pressure of 6 atm for 14 h. When the absorption of hydrogen ceased, methanol (180 ml) and the mixture of glyoxylic acid monohydrate (27.8 g, 0.3 mol) and triethylamine (40.5 g, 0.4 mol) were introduced to the system. The reaction system was heated to 50C and hydrogen was introduced under the pressure of 10 atm. The reductive amination was carried out for 15 h, then the catalyst was filtered and the solvent evaporated by means of a rotary vacuum evaporator. The solid obtained was dissolved in water and acidified with 10% hydrochloric acid to pH=2.0. Crystallization was carried out for 10 h at 8C. 35.5 g of the product N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid hydrochloride trihydrate was separated with the overall yield 84% with respect to the starting ethylenediamine. The raw product was recrystallized form the 85% ethanol. The structure of the product was confirmed by means of 1H NMR and the purity thereof by means of elemental microanalysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Ru(salen)(NO)(Cl) This complex was synthesized following a similar procedure described by Mitchell-Koch J.T., Reed T.M., and Borovik A.S., Light-Activated Transfer of Nitric Oxide From a Porous Material, Angew. Chem. Int. Ed., 43(21), 2806-2809 (2004). See also Works, C. F.; Ford, P. C. Photoreactivity of the ruthenium nitrosyl complex, Ru(salen)(Cl)(NO), Solvent effects on the back reaction of NO with the Lewis acid Rum(salen)(Cl), J. Am. Chem. Soc, 122, 7592-7593 (2002); Works, C. F., Jocher, C. J., Bart, G. D., Bu, X. & Ford, P. C. Photochemical nitric oxide precursors: synthesis, photochemistry, and ligand substitution kinetics of ruthenium salen nitrosyl and ruthenium salophen nitrosyl complexes. Inorg. Chem., 41, 3728-3739 (2002); Bordini, J., Hughes, D. L., Da Motta Neto, J. D. & da Cunha, C. J. Nitric oxide photorelease from ruthenium salen complexes in aqueous and organic solutions, Inorg. Chem., 41, 5410-5416 (2002). Under an argon atmosphere, a 50 mL DMF solution of salen (1.0034 g, 3.7441 mmol) was treated with 2 equivalents of solid KH (0.300 g, 7.48 mmol). After H2 evolution was completed (about 30 minutes), Ru(NO)Cl3 (0.890 g, 3.75 mmol) was added. This reaction mixture was taken out of the dry box and was refluxed for 2 hours under N2. The DMF was removed under reduced pressure and the solid residue was allowed to cool overnight. The brown solid was further purified using silica gel flash chromatography with a mobile phase of 2% methanol/98% CH2Cl2. Fractions containing Ru(salen)(NO)(Cl) were combined and the solvent was removed under reduced pressure to yield 0.724 g (60%) of a brown solid. 1H NMR: (CDCl3, ppm) delta = 3.97 - 4.02 and 4.36 - 4.41 (dd, 4H, CH2CH2); 6.68 - 6.71 (t, 2H, salicyl phenyl); 7.24 - 7.26 (d, 2H, salicyl phenyl); 7.30 - 7.32 (d, 2H, salicyl phenyl); 7.41 - 7.45 (t, 2H, salicyl phenyl); 8.26 (s, 2H, -NCH(Ph)). IR: (KBr, cm-1) 1832 (NO), 1603 (C=N), 1520 (C=C), see Works C. F., Jocher C. J., Bart G. D., Bu X., and Ford P. C, Photochemical Nitric Oxide Precursors: Synthesis, Photochemistry, and Ligand Substitution Kinetics of Ruthenium Salen Nitrosyl and Ruthenium Salophen Nitrosyl Complexes, Inorg. Chem., 41(14), 3728-3739 (2002). lambdamax/nm: (CH2Cl2) 378; (suspension in phosphate buffer solution, nm) 249, 271 (sh), 383. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With oxygen; In methanol; at 20℃; | General procedure: The synthesis of these complexes was accomplished by a procedure slightly different form that reported in the literature [31,32]. A number of the vanadium derivatives used in the literature were tested as precursors, i.e. VO(acetylacetonate)2 [31], vanadyl sulfate di-hydrate [29,33], and V(acetylacetonate)3 [34]. The best results were obtained with VIII(acac)3, in terms of reproducibility of the reaction and solubility of complexes. (0020) General procedure: The Schiff base was dissolved in 100 ml of boiling methanol, or suspended when scarcely soluble. The equimolar amount of V(acac)3 was completely dissolved in the minimum volume of MeOH with the help of sonication and added dropwise to the solution (or to the suspension), causing immediate color change from yellow to green. After an overnight stirring in an open vessel at room temperature, the reaction was stopped and the precipitated solid was collected, washed with diethyl ether, and dried. No trace of Schiff base was present. Eventually unreacted V(acac)3 was washed off with warm acetone. (0021) The following VIVO complexes were prepared, their purity was checked with TLC and HPLC analyses. (0022) SalophenVIVO, yield 73%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 242 (40,000), 314 (22,000) and 396 (18,000); 5,5?-Cl2salophenVIVO, yield 78%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 305 (12,000), 409 (10,700); 5,5?-(t-Bu)2salophenVIVO, yield 82%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 246 (40,900), 318 (22,700), 409 (15,400); 3,3?-(OMe)2salophenVIVO, yield 79%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 221 (42,000), 301 (24,000), 313 (22,000) and 335 (13,000); 5,5?-(OMe)2salophenVIVO, yield 87%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 216 (70,000), 243 (41,000), 289 (30,000), 300 (32,000), 337 (26,000) and 434 (9000); 3,3?,5,5?-Cl4SalophenVIVO: yield 78%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 315 (9800), 412 (10,000); 3,3?,5,5?-(t-Bu)4salophenVIVO, yield 87%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 250 (43,300), 327 (25,900), 416 (16,100). (0023) SalenVIVO, yield 89%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 242 (39,000), 277 (18,000) and 362 (7900); 5,5?-Cl2salenVIVO, yield 67% UV-vis in MeCN [lambdamax, nm] 248 (49,000), 280 sh, 370 (7400); 5,5?-(t-Bu)2salenVIVO, yield 67%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 246 (56,000), 278 (27,000), 370 (9200); 3,3?-(OMe)2salenVIVO, yield 93%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 224 (16,000), 296 (14,000) and 381 (2800); 5,5?-(OMe)2salenVIVO, yield 86%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 251 (20,000), 286 sh (8800) and 392 (9000); 3,3?,5,5?-Cl4salenVIVO, yield 70%, UV-vis in MeCN: lambdamax = 370 nm (does not dissolve completely); 3,3?,5,5?-(t-Bu)4salenVIVO, yield 72%, UV-vis in CH2Cl2 [lambdamax, nm (?, M-1 cm-1)] 252 (41,000), 288 (27,000) and 386 (3600). UV-vis spectra are consistent with literature data [35,36]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With oxygen; In methanol; at 20℃; | General procedure: The synthesis of these complexes was accomplished by a procedure slightly different form that reported in the literature [31,32]. A number of the vanadium derivatives used in the literature were tested as precursors, i.e. VO(acetylacetonate)2 [31], vanadyl sulfate di-hydrate [29,33], and V(acetylacetonate)3 [34]. The best results were obtained with VIII(acac)3, in terms of reproducibility of the reaction and solubility of complexes. (0020) General procedure: The Schiff base was dissolved in 100 ml of boiling methanol, or suspended when scarcely soluble. The equimolar amount of V(acac)3 was completely dissolved in the minimum volume of MeOH with the help of sonication and added dropwise to the solution (or to the suspension), causing immediate color change from yellow to green. After an overnight stirring in an open vessel at room temperature, the reaction was stopped and the precipitated solid was collected, washed with diethyl ether, and dried. No trace of Schiff base was present. Eventually unreacted V(acac)3 was washed off with warm acetone. (0021) The following VIVO complexes were prepared, their purity was checked with TLC and HPLC analyses. (0022) SalophenVIVO, yield 73%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 242 (40,000), 314 (22,000) and 396 (18,000); 5,5?-Cl2salophenVIVO, yield 78%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 305 (12,000), 409 (10,700); 5,5?-(t-Bu)2salophenVIVO, yield 82%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 246 (40,900), 318 (22,700), 409 (15,400); 3,3?-(OMe)2salophenVIVO, yield 79%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 221 (42,000), 301 (24,000), 313 (22,000) and 335 (13,000); 5,5?-(OMe)2salophenVIVO, yield 87%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 216 (70,000), 243 (41,000), 289 (30,000), 300 (32,000), 337 (26,000) and 434 (9000); 3,3?,5,5?-Cl4SalophenVIVO: yield 78%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 315 (9800), 412 (10,000); 3,3?,5,5?-(t-Bu)4salophenVIVO, yield 87%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 250 (43,300), 327 (25,900), 416 (16,100). (0023) SalenVIVO, yield 89%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 242 (39,000), 277 (18,000) and 362 (7900); 5,5?-Cl2salenVIVO, yield 67% UV-vis in MeCN [lambdamax, nm] 248 (49,000), 280 sh, 370 (7400); 5,5?-(t-Bu)2salenVIVO, yield 67%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 246 (56,000), 278 (27,000), 370 (9200); 3,3?-(OMe)2salenVIVO, yield 93%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 224 (16,000), 296 (14,000) and 381 (2800); 5,5?-(OMe)2salenVIVO, yield 86%, UV-vis in MeCN [lambdamax, nm (?, M-1 cm-1)] 251 (20,000), 286 sh (8800) and 392 (9000); 3,3?,5,5?-Cl4salenVIVO, yield 70%, UV-vis in MeCN: lambdamax = 370 nm (does not dissolve completely); 3,3?,5,5?-(t-Bu)4salenVIVO, yield 72%, UV-vis in CH2Cl2 [lambdamax, nm (?, M-1 cm-1)] 252 (41,000), 288 (27,000) and 386 (3600). UV-vis spectra are consistent with literature data [35,36]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol;Reflux; | General procedure: Manganese (II) chloride, cobalt (II) chloride, nickel (II) chloride and copper (II) chloride complexes of Schiff base were prepared as follows: (0008) The required weights of the inorganic salts were dissolved in EtOH (20 cm3) for Schiff base and refluxed with the desired weight of the ligand in EtOH (20 cm3) for Schiff base. The reaction mixture was refluxed with stirring. The corresponding solid complexes were filtered, washed several times with EtOH and dried under vacuum over P4O10. The analytical data for the prepared metal complexes are collected in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol;Reflux; | General procedure: Manganese (II) chloride, cobalt (II) chloride, nickel (II) chloride and copper (II) chloride complexes of Schiff base were prepared as follows: (0008) The required weights of the inorganic salts were dissolved in EtOH (20 cm3) for Schiff base and refluxed with the desired weight of the ligand in EtOH (20 cm3) for Schiff base. The reaction mixture was refluxed with stirring. The corresponding solid complexes were filtered, washed several times with EtOH and dried under vacuum over P4O10. The analytical data for the prepared metal complexes are collected in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol;Reflux; | General procedure: Manganese (II) chloride, cobalt (II) chloride, nickel (II) chloride and copper (II) chloride complexes of Schiff base were prepared as follows: (0008) The required weights of the inorganic salts were dissolved in EtOH (20 cm3) for Schiff base and refluxed with the desired weight of the ligand in EtOH (20 cm3) for Schiff base. The reaction mixture was refluxed with stirring. The corresponding solid complexes were filtered, washed several times with EtOH and dried under vacuum over P4O10. The analytical data for the prepared metal complexes are collected in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In methanol; for 1h;Reflux; | General procedure: Corresponding metal salt solution (1 mmol) and Schiff base ligand(1 mmol) were dissolved in methanol (10 mL) and reflux for 1 h.Crystals of the metal complexes were obtained by cooling the reactionmixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | In methanol; for 1h;Reflux; | General procedure: Corresponding metal salt solution (1 mmol) and Schiff base ligand(1 mmol) were dissolved in methanol (10 mL) and reflux for 1 h.Crystals of the metal complexes were obtained by cooling the reactionmixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In methanol; for 1h;Reflux; | General procedure: Corresponding metal salt solution (1 mmol) and Schiff base ligand(1 mmol) were dissolved in methanol (10 mL) and reflux for 1 h.Crystals of the metal complexes were obtained by cooling the reactionmixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12%; 68% | In toluene;Schlenk technique; Inert atmosphere; | General procedure: A powder of Al(O-i-Pr)3 (0.76 g, 3.72 mmol) was added portionwise to a solution of ligand 1 (1.00 g, 3.72 mmol) in toluene (20 ml). Almost immediately a white precipitate was formed. The reaction mixture was stirred overnight. The solid was filtered off and washed thoroughly with toluene (2 × 10 ml). The obtained white powder was dried in vacuum, yielding 2 (0.72 g, 68%). All volatiles from the mother liquor were removed under reduced pressure and the residue was recrystallized from CH2Cl2, yielding (Salen)Al(O-i-Pr) (3) (0.16 g, 12%). The spectral data for 3 corresponds to literature data [10]. Crystals of complex 2 suitable for X-ray analysis were grown from CH2Cl2 at -30 C. The compound 2 was obtained analogously in THF and CH2Cl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In toluene;Schlenk technique; Inert atmosphere; | General procedure: A powder of Al(O-i-Pr)3 (0.76 g, 3.72 mmol) was added portionwise to a solution of ligand 1 (1.00 g, 3.72 mmol) in toluene (20 ml). Almost immediately a white precipitate was formed. The reaction mixture was stirred overnight. The solid was filtered off and washed thoroughly with toluene (2 × 10 ml). The obtained white powder was dried in vacuum, yielding 2 (0.72 g, 68%). All volatiles from the mother liquor were removed under reduced pressure and the residue was recrystallized from CH2Cl2, yielding (Salen)Al(O-i-Pr) (3) (0.16 g, 12%). The spectral data for 3 corresponds to literature data [10]. Crystals of complex 2 suitable for X-ray analysis were grown from CH2Cl2 at -30 C. The compound 2 was obtained analogously in THF and CH2Cl2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; | Nickel (II) acetate tetrahydrate (9.27 g, 0.037 moles) and salenH2 (2,2?-[1,2-Ethanediylbis[(E)-nitrilomethylidyne] ]bis-phenol) (10 g, 0.037 moles) were physically mixed together (Molar ratio 1:1). To this 0.3 equivalents of HPLC grade methanol was added (0.0111, 0.449 mL). This paste was manually fed into the ThermoFisher Process 11 Extruder, with a screw speed of 55 rpm (residence time Ca. 1.5 - 2 minutes). A brick red solid was produced. PXRD of the as-synthesised extrudate suggest a complete reaction in both cases as the traces are very similar to the simulated trace produced by the Cambridge Structure Database (Figure 15). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In methanol; ethanol for 2h; Reflux; | The Mn(III) salen complex was synthesized following the procedure given in the literature,[2] by refluxing the ethanolic solution of salen ligand and methanolic solution of MnCl2.4H2O in a mole ratio of 1:1 for 2 h. During the reaction the bright yellow color of the solution changes to dark brown. The dark brown solution was concentrated to obtain a dark brown solid. The obtained dark brown solid (yield =73%) was designated as Mn(salen). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In ethanol; water; for 1.0h; | Salicylaldehyde (10.84 g, 89 mmol) was added to 80 mL absolute ethanol and stirred magnetically at 80C. Then, 2.22 g ethylenediamine (37 mmol) was dropped slowly and the solution became yellow. The solution was allowed to stir at 80C for another 1.5 h. Co(CH3COO)2*4H2O (9.30 g, 37 mmol) aqueous solution (50 mL) was dropped slowly into the reaction mixture and the solution became red and appeared dark red precipitation. After reacted for 1 h, the reaction mixture was filtrated and washed by H2O and ethanol three times (3 × 20 mL). The product (Co-Salen complex) was dried under a reduce pressure at 60C for 12 h with yield of 73% based on the amount of ethyldiamine. MS(+ESI) of Co-Salen (%): m/z = 325 (100) (M + H)+; Element analysis for Co-Salen, C: 58.87%, H: 3.85%, N: 8.11%; Calculated value for Co-Salen: C: 59.09%, H: 4.34%, N: 8.61%. |
In ethanol; water; for 1.0h;Inert atmosphere; Reflux; | Cobalt(II)-salen complexes are synthesized by established procedures[44]. Parent salen ligand 1.8 mM (0.5 g in ethanol) isdegassed under N2. Co(OAc)2.4H2O (0.46 g, 1.8 mmol) in warmwater is added to salen solution in small quantities at a time underN2 atmosphere. Immediately the yellow color was changed into thedark brown. The reaction mixture is refluxed under N2 for onehour, cooled and dried in vacuum. The product is extracted withCHCl3 and dried in vacuum. Dark brown colored cobalt(II)-salencomplex I is obtained. The similar procedure is followed to thesynthesis of complexes II-V using appropriate salen ligand. | |
In ethanol; at 90.0℃; for 24.0h;Inert atmosphere; | The Co(salen) complex was prepared by a typical procedure21. H2(salen) (805 mg) and ethanol (10mL) were mixed under an Ar atmosphere and the solution was heated to 90 C in an oil bath.(CH3COO)2Co4H2O (375 mg) as a Co precursor in ethanol was added to the solution. After stirringfor 24 h, the solution was cooled to room temperature and filtered to remove the remaining H2(salen)and Co2+ ions, followed by drying under vacuum for a day. The Co(salen) complex was obtained asan orange powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; at 110℃; for 5h;Inert atmosphere; | General procedure: Ligand (1 mmol) was dissolved in 20 mL toluene in a round-bottom ask. Then an equivalentamount of the boron derivative which approximately corresponds to 1 mmol was added,after which the ligand solution turned completely clear. The reaction mixture was stirred at110C for 5 h . Dierent gradations of yellow precipitates were ltered, washed with excesssolvent and dried in a ventilated oven. The proposed reactions for formation of BL1 and BL2are depicted in gures 2 and 3 [28]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; at 110℃; for 5h;Inert atmosphere; | General procedure: Ligand (1 mmol) was dissolved in 20 mL toluene in a round-bottom ask. Then an equivalentamount of the boron derivative which approximately corresponds to 1 mmol was added,after which the ligand solution turned completely clear. The reaction mixture was stirred at110C for 5 h . Dierent gradations of yellow precipitates were ltered, washed with excesssolvent and dried in a ventilated oven. The proposed reactions for formation of BL1 and BL2are depicted in gures 2 and 3 [28]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; at 110℃; for 5h;Inert atmosphere; | General procedure: Ligand (1 mmol) was dissolved in 20 mL toluene in a round-bottom ask. Then an equivalentamount of the boron derivative which approximately corresponds to 1 mmol was added,after which the ligand solution turned completely clear. The reaction mixture was stirred at110C for 5 h . Dierent gradations of yellow precipitates were ltered, washed with excesssolvent and dried in a ventilated oven. The proposed reactions for formation of BL1 and BL2are depicted in gures 2 and 3 [28]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; at 110℃; for 5h;Inert atmosphere; | General procedure: Ligand (1 mmol) was dissolved in 20 mL toluene in a round-bottom ask. Then an equivalentamount of the boron derivative which approximately corresponds to 1 mmol was added,after which the ligand solution turned completely clear. The reaction mixture was stirred at110C for 5 h . Dierent gradations of yellow precipitates were ltered, washed with excesssolvent and dried in a ventilated oven. The proposed reactions for formation of BL1 and BL2are depicted in gures 2 and 3 [28]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; at 110℃; for 5h;Inert atmosphere; | General procedure: Ligand (1 mmol) was dissolved in 20 mL toluene in a round-bottom ask. Then an equivalentamount of the boron derivative which approximately corresponds to 1 mmol was added,after which the ligand solution turned completely clear. The reaction mixture was stirred at110C for 5 h . Dierent gradations of yellow precipitates were ltered, washed with excesssolvent and dried in a ventilated oven. The proposed reactions for formation of BL1 and BL2are depicted in gures 2 and 3 [28]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: ethylenediamine In ethanol at 20℃; Green chemistry; Stage #2: salicylic alcohol With oxygen In ethanol at 20℃; for 1.46667h; Green chemistry; | General procedure for direct preparation of Schiff base and oxime compounds catalyzed by PSA-Schiffbase-Mn(III) complex General procedure: In an oven-dried 10-mL round-bottom flask, 10 mg catalyst 4 (3.2 mol%) along with 1 mmol amine or hydroxyl amine was added to 7 mL absolute ethanol at ambient temperature.Then, 1 mmol of alcohol was added to the reaction mixture and stirred under O2 atmosphere (~1 atm.). After 14-60 min,yellow to red sediments were appeared which show successful oxidation of alcohols followed by imine formation. The product was filtered and added to 20 mL of hot methanol which just dissolved the imine compound. The filtration of the reaction mixture left a solid on the filter that was the catalyst 4. The remained solution set a side overnight for crystallization, and the recovered catalyst was reused for the next run (Scheme 2). |
79% | With oxygen In toluene at 90℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In methanol; for 1h;Reflux; | General procedure: Corresponding metal salt solution (1 mmol) and Schiff base ligand(1 mmol) were dissolved in methanol (10 mL) and reflux for 1 h.Crystals of the metal complexes were obtained by cooling the reactionmixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | In methanol; for 1h;Reflux; | General procedure: Corresponding metal salt solution (1 mmol) and Schiff base ligand(1 mmol) were dissolved in methanol (10 mL) and reflux for 1 h.Crystals of the metal complexes were obtained by cooling the reactionmixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In methanol; for 1h;Reflux; | General procedure: Corresponding metal salt solution (1 mmol) and Schiff base ligand(1 mmol) were dissolved in methanol (10 mL) and reflux for 1 h.Crystals of the metal complexes were obtained by cooling the reactionmixture. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44.0% | In acetonitrile; at 25℃; for 24h;Inert atmosphere; Schlenk technique; | A 0.745g (4.647mmol) sample of H2Salen was added to a stirred solution of 1.274g (4.647mmol) of HMeSi(NCS)2 in acetonitrile (20mL). The reaction mixture was stirred for 24h at room temperature producing a pale yellow solid that was dissolved by heating the solution to ca 80C, filtering it off and slowly cooling it to 20C. The pale yellow crystals that formed were filtered off, washed with 20mL of diethyl ether and dried under vacuum (0.1mbar, 2h). Yield: 0.755g (44.0%). Mp: 210C (dec). Anal. Calc. for C18H17N3O2SSi (367.50): C, 58.83; H, 4.66; N, 11.43; S, 8.73. Found: C, 58.83; H, 4.68; N, 11.48; S, 8.77%. 1H NMR (200MHz, C2D4Cl2): delta=0.06 (s, 3H, SiCH3), delta=4.25 (s, 2H, CH2), delta=6.96-7.53 (m, 4H, C6H4 aromatic), delta=8.67 (s, 1H, N=CH). 1H NMR (200MHz, dmso-d6): delta=-0.08 (s, 3H, SiCH3), delta=4.08 (s, 2H, CH2), delta=6.96-7.53 (m, 4H, C6H4 aromatic), delta=8.67 (s, 1H, N=CH). 1H NMR (200MHz, acetone-d6) mixture of two stereoisomers: delta=0.06 and 0.20 (s, SiCH3), delta=4.25 and 4.26 (2H, CH2), delta=6.84-7.53 (m, 4H, C6H4 aromatic), delta=8.55 and 8.78 (s, 1H, N=CH). 1H NMR (200MHz, C2D4Cl2) mixture of two stereoisomers: delta=0.02 and 0.24 (s, SiCH3), delta=3.96 and 4.03 (s, CH2), delta=6.84-7.53 (m, C6H4 aromatic), delta=8.13 and 8.39 (s, 1H, N=CH). 13C NMR (50MHz, dmso-d6): delta=9.55 (SiCH3), delta=51.94 (CH2) delta=119.27, 121.19, 133.78, 137.05 (CH aromatic), delta=165.86 (N=CH), delta=159.98 (Cipso-CH=N), (NCS) not detected. 29Si INEPT NMR (59.6MHz, dmso-d6): delta=-168.75. 29Si CP/MAS NMR (59.6MHz): delta=-177.15. FT-IR: nu(-NCS) 2115cm-1, nu(N=C) 1641cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With sodium hydroxide In methanol; dichloromethane at 20℃; for 12h; | Synthesis of [Cu2(L2)2] (2) 2 has also been synthesized according to the procedure adopted for1 (Scheme 3). The Schiff base ligand (H2L2) are generated in situ by thecombination of benzaldehyde and ethylenediamine in 2:1 M ratio withmix solvent (15 ml methanol and 15 ml dichloromethane). The solutionis then set to reflux with continuous stirring for 3 h at 60 °C and isallowed to stand for cooling at room temperature. This cooling is followedby the dropwise addition of Cu(OAc)2·H2O (1 mmol, 0.199 g) andthen 1 mmol NaOH to the Schiff base ligand (H2L2) that turns the solutioninto green. The solution is stirred overnight at ambient temperature.The resulting solution is filtered. Dark blue block shapedcrystals of 2 suitable for X-ray analysis have been obtained within aperiod of two weeks. The solubility of synthesized complex has beenfound in acetonitrile, acetone and water. The complex decomposes at240 °C. Yield: 48%. |
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
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P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
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P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
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P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
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P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
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P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
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P350 | Gently wash with plenty of soap and water. |
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P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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