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Chemical Structure| 136768-57-5
Chemical Structure| 136768-57-5
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Product Details of [ 136768-57-5 ]

CAS No. :136768-57-5 MDL No. :MFCD29039185
Formula : C16H22N4 Boiling Point : -
Linear Structure Formula :- InChI Key :NJAHJMGPPKJUTO-UHFFFAOYSA-N
M.W : 270.37 Pubchem ID :11021969
Synonyms :

Safety of [ 136768-57-5 ]

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:

Application In Synthesis of [ 136768-57-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 136768-57-5 ]

[ 136768-57-5 ] Synthesis Path-Downstream   1~82

  • 4
  • potassium aquapentachlororuthenate(III) [ No CAS ]
  • [ 136768-57-5 ]
  • cis-{Ru(III)N,N'-dimethyl-N,N''-bis(pyridylmethyl)ethylenediamineCl2}Cl [ No CAS ]
  • 5
  • mercury(II) perchlorate [ No CAS ]
  • [ 27731-44-8 ]
  • sodium perchlorate [ No CAS ]
  • [ 136768-57-5 ]
  • cis-α-aquahydroxo(N,N'-bis(2-pyridylmethyl)-N,N'-dimethyl-1,2-ethanediamine)chromium(III) perchlorate [ No CAS ]
  • 6
  • manganese(II) chloride tetrahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [ 260431-32-1 ]
YieldReaction ConditionsOperation in experiment
65% In acetonitrile; at 20℃; for 15h; According to ref [56] MnCl2,4H2O (0.48 g, 2.4 mmol) was added to a solution of L(0.54 g, 2 mmol) in 3 mL of acetonitrile. The mixture was stirred at room temperature for15 h and the solvent was removed under vacuum. The grey powder obtained was washedtwice with diethyl ether and after recrystallization by diffusion of diethyl ether into a solutionof the product in an acetonitrile-ethanol mixture, (L)MnCl2 (0.52 g, 65% yield) wasobtained as a white powder.Anal. Calc. for C16H22Cl2MnN4·0.5EtOH: C, 48.70; H, 6.01; N, 13.36. Found: C, 49.02;H, 5.98; N, 13.40.
  • 7
  • [ 136768-57-5 ]
  • iron(II) sulfate [ No CAS ]
  • cis-[Fe(N,N'-bis(2-pyridylmethyl)-N,N'-dimethyl-1,2-ethanediamine)bis-isothiocyanate] [ No CAS ]
  • 8
  • iron(II) perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [ 75-05-8 ]
  • [bis(acetonitrile)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-diaminoethane)iron(II)] perchlorate [ No CAS ]
  • 9
  • [ 10025-98-6 ]
  • sodium perchlorate [ No CAS ]
  • [ 136768-57-5 ]
  • Pd(C2H4(N(CH3)CH2C5H4N)2)(2+)*2ClO4(1-)=[Pd(C2H4(N(CH3)CH2C5H4N)2)](ClO4)2 [ No CAS ]
  • 10
  • [ 1020-31-1 ]
  • [ 143-66-8 ]
  • [ 7705-08-0 ]
  • [ 136768-57-5 ]
  • (N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)((Me3C)2C6H2O2)iron(III) tetraphenylborate [ No CAS ]
  • 11
  • iron perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [ 75-05-8 ]
  • [bis(acetonitrile)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-diaminoethane)iron(II)] perchlorate [ No CAS ]
  • 12
  • silver hexafluoroantimonate [ No CAS ]
  • iron(II) chloride hydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [ 75-05-8 ]
  • [Fe(C2H4(NCH3CH2C5H4N)2)(CH3CN)2](2+)*2SbF6(1-)=[Fe(C2H4(NCH3CH2C5H4N)2)(CH3CN)2](SbF6)2 [ No CAS ]
  • 13
  • tetraethylammonium μ-oxohexachlorodiferrate(III) [ No CAS ]
  • [ 136768-57-5 ]
  • [(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)ClFeOFeCl(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)]Cl2 [ No CAS ]
  • 14
  • iron perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [ 1310-73-2 ]
  • bis(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)(μ-oxo)(hydroxo)aquadiiron(III) perchlorate [ No CAS ]
  • bis(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)(μ-oxo)(μ-hydroxo)diiron(III) perchlorate [ No CAS ]
  • 15
  • iron perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [ 1310-73-2 ]
  • [(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)(H2O)Fe(μ-O)Fe(OH)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)](ClO4)3 * H2O [ No CAS ]
  • 16
  • [ 7705-08-0 ]
  • [ 136768-57-5 ]
  • [(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)FeCl2]Cl [ No CAS ]
  • 17
  • manganese(II) perchlorate hexahydrate [ No CAS ]
  • [ 7722-84-1 ]
  • [ 143-66-8 ]
  • [ 136768-57-5 ]
  • [ 75-05-8 ]
  • [(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)2Mn2(μ-O)2](BPh4)2(ClO4)*CH3CN [ No CAS ]
  • 18
  • iron perchlorate hexahydrate [ No CAS ]
  • [ 7732-18-5 ]
  • [ 136768-57-5 ]
  • [ 57-13-6 ]
  • bis(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)(μ-oxo)(μ-ureato)diiron(III) perchlorate monohydrate [ No CAS ]
  • 19
  • iron(II) trifluoromethanesulfonate acetonitrile disolvate [ No CAS ]
  • [ 7732-18-5 ]
  • [ 136768-57-5 ]
  • [(α-N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-ethane-1,2-diamine)Fe(μ-OH)]2(CF3SO3)3 [ No CAS ]
  • 20
  • manganese(II) chloride tetrahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • cis-[(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)Mn(Cl)2]*0.5H2O [ No CAS ]
  • 21
  • iron perchlorate hexahydrate [ No CAS ]
  • [ 64-17-5 ]
  • [ 136768-57-5 ]
  • [ 57-13-6 ]
  • urea(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)(ethoxy)iron(III) perchlorate [ No CAS ]
  • 22
  • iron(III) perchlorate decahydrate [ No CAS ]
  • [ 6131-90-4 ]
  • [ 136768-57-5 ]
  • Fe2O(4+)*2C16H22N4*CH3COO(1-)*3ClO4(1-)=[Fe2(C16H22N4)2O(CH3COO)](ClO4)3 [ No CAS ]
  • 23
  • [ 197524-22-4 ]
  • [ 136768-57-5 ]
  • [ 1151470-94-8 ]
  • 24
  • nickel(II) chloride hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [Ni(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethylenediamine)]Cl2*3H2O [ No CAS ]
  • 25
  • [ 67-56-1 ]
  • nickel(II) perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [Ni(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethylenediamine)](ClO4)2*CH3OH*H2O [ No CAS ]
  • 26
  • [ 766-76-7 ]
  • [ 136768-57-5 ]
  • iron(III) perchlorate [ No CAS ]
  • [Fe(III)2(μ-O)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)2(μ-benzoate)](ClO4)3 [ No CAS ]
  • 27
  • salicylate [ No CAS ]
  • [ 136768-57-5 ]
  • iron(III) perchlorate [ No CAS ]
  • [ 871467-57-1 ]
  • 28
  • iron perchlorate hexahydrate [ No CAS ]
  • [ 429-41-4 ]
  • [ 136768-57-5 ]
  • [ 75-05-8 ]
  • [diiron(III)(μ-oxo)bis(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)difluoro] perchlorate - acetonitrile (1/2) [ No CAS ]
  • 29
  • [ 7705-08-0 ]
  • [ 136768-57-5 ]
  • cis-(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-ethanediamine)-dichloroiron(III)(1+) [ No CAS ]
  • 30
  • copper(II) perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [ 1173273-18-1 ]
  • 31
  • copper(II) chloride hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • (N,N'-dimethyl-N,N'-bis(pyridin-2-ylmethyl)-1,2-diaminoethane)copper(II) chloride dihydrate [ No CAS ]
  • 32
  • [ 6959-47-3 ]
  • [ 110-70-3 ]
  • [ 136768-57-5 ]
YieldReaction ConditionsOperation in experiment
89% The ligand BPMEN was synthesized via a previouslyreported procedure (Singh et al. 2017). A solution of potassiumcarbonate (5.1 g, 37 mmol) in 15 mL water was dropwiseadded to the aqueous solution of 2-(chloromethyl)-pyridine hydrochloride (3 g, 18.3 mmol in 10 mL). Afterabout 30 min of stirring at room temperature, the reactionmixture was extracted with dichloromethane (3 × 20 mL).The combined organic extracts were dried over anhydroussodium sulfate. The solution was filtered, and the solventwas removed under vacuum. The resulted residue was thendissolved in dichloromethane (10 mL). The above solutionwas added dropwise to a solution of N,N′-dimethylethylenediamine(0.942 mL, 8.75 mmol) in dichloromethane(25 mL). After this addition, 20 mL of aqueous sodiumhydroxide (1 M) was added slowly and the reaction mixturewas stirred for next 60 h at room temperature. After stirringwas finished, another fraction of sodium hydroxide (20 mL,1 M) was added rapidly. The reaction mixture was extractedwith dichloromethane (3 × 50 mL) and the combined organicportion was dried over anhydrous sodium sulfate. Evaporationof solvent led to isolation of the ligand BPMEN as adark orange oil. (2.1 g, Yield - 89%) 1H NMR (500 MHz,Methanol-d4) δ 8.45 (d, 2H, pyridine ring), 7.76 (m, 2H, pyridinering), 7.52 (d, 2H, pyridine ring), 7.30 (m, 2H, pyridinering), 3.67 (s, 4H, -N-CH2-Py), 2.63 (s, 4H, -CH2-CH2-),2.26 (s, 6H, N-CH3). ESI-MS+: [BPMEN + H]+ = 271.15 m/z+ (experimental) 271.19 m/z+ (theoretical).
79% With triethylamine; In tetrahydrofuran; for 18h;Reflux; A solution of N,N′-dimethylethylenediamine (1.72g, 20mmol) in dry tetrahydrofuran (60mL) was treated with 2-chloromethylpyridine hydrochloride (6.604g, 40mmol) and triethylamine (8.093g, 80mmol) and the mixture was stirred under reflux for 18h. The resulting mixture was cooled to in ice and the triethylamine hydrobromide was removed by filtration. The filtrate was then treated with 10mL 15% NaOH solution and extracted with CH2Cl2 (3×40mL). The combined extracts were dried over anhydrous MgSO4. Removal of the solvent with rotary evaporator yielded dark brown oil which was chromatographed on alumina and eluted with 95/5 (v/v) mixture of ethyl acetate/MeOH (Rf=0.81). The purified ligand was obtained as yellow viscous oil (yield: 4.2g, 79%). Selected IR bands (cm-1): ν(C-H) 3064 (w), 2949 (m), 2802 (m); pyridyl groups: 1592 (s), 1577 (m), 1474 (m), 1435 (s). 1H NMR: 8.43 (m, 2H), 7.70 (m, 2H), 7.37 (m, 2H), 7.72 (m, 2H), 3.58 (s, 4H), 2.51 (s, 4H), 2.14 (s, 6H); 13C NMR: 159.74 (2-py), 149.06 (6-py), 136.78 (4-py), 123.01 (3-py), 122.42 (5-py), 63.95 (N-CH2-py), 35.40 (-CH2-CH2-N), 42.94 (CH3-N), 40.60 (CH3-N).
79% The ligand L1 was synthesized via previously reported procedure[23]. A solution of potassium carbonate (2.55 g, 18.45 mmol)in 10 mL water was dropwise added to the aqueous solution of 2-(chloromethyl)-pyridine hydrochloride (1.5 g, 9.15 mmol in10 mL). After about 30 min. of stirring at room temperature, thereaction mixture was extracted with dichloromethane(3 20 mL). The combined organic extracts were dried over anhydroussodium sulfate. The solution was filtered and the solvent wasremoved under vacuum. The resulted residue was then dissolvedin dichloromethane (10 mL). The dichloromethane solution of 2-chloromethyl-pyridine was added dropwise to a solution of N,N0-dimethylethylenediamine (0.471 mL, 5.34 mmol) in dichloromethane(15 mL). After this addition, 10 mL of aqueous sodiumhydroxide (1 M) was added slowly and the reaction mixture wasstirred for next 60 h at room temperature. After stirring was finished,another fraction of sodium hydroxide (10 mL, 1 M) wasadded rapidly. The reaction mixture was extracted with dichloromethane(3 25 mL) and combined organic portion was dried overanhydrous sodium sulfate. Evaporation of solvent led to isolationof the ligand L1 as a dark orange oil. (1.13 g, Yield 79%) 1H NMR(500 MHz, Methanol-d4) d 7.27 (m, 2H, pyridine ring), 7.50 (d,2H, pyridine ring), 7.76 (m, 2H, pyridine ring), 8.45 (d, 2H, pyridinering), 3.68 (s, 4H, -N-CH2-Py), 2.63 (s, 4H, -CH2-CH2-), 2.26 (s, 6H,N-CH3). IR (cm1): 2945, 2789, 1589, 1569, 1472, 1432, 1360,1304, 1146, 1090, 1031, 994, 635, 614, 418.
70% Synthesis of [N,N′-Dimethyl-N,N′-bis-(pyridine-2-ylmethyl)-1,2-diaminoethane] was taken from a previously reported procedure [16]. 2-(chloromethyl)pyridine hydrochloride (1.501 g, 9.15 mmol) dissolved in 5 mL deionized (DI) water was added dropwise to an aqueous solution containing K2CO3 (2.556 g, 18.49 mmol) dissolved in 7.5 mL DI water. The resulting mixture was stirred for 30 min. The mixture was extracted with CH2Cl2 (3×10 mL). The organic phase was collected and dried with anhydrous Na2SO4. The dried solution was concentrated in vacuo to afford orange oil. A solution containing N,N′-dimethylethylenediamine (0.471 mL, 4.38 mmol) in 15 mL CH2Cl2 was added dropwise to the aforementioned orange oil dissolved in 5 mL CH2Cl2. An aqueous solution containing NaOH (0.311 g, 7.78 mmol) dissolved in 7.6 mL DI water was slowly added to organic mixture and stirred at room temperature. After 60 h, a second portion of NaOH solution(0.318 g, 7.95 mmol) was quickly added to the mixture. The combined mixture was extracted with CH2Cl2 (3×20 mL) and dried with anhydrous Na2SO4. The organic solution was concentrated in vacuo to afford a brown oil, BPMEN (Yield: 0.631 g, 2.33 mmol, 70%) 1H NMR(500 MHz, CD2Cl2) δ 8.46 (dt, 2H, pyridine ring), 7.80 (m, 2H, pyridinering), 7.51 (m, 2H, pyridine ring), 7.30 (m, 2H, pyridine ring), 3.70 (m,4H, -CH2), 2.66 (m, 4H, -CH2), 2.27 (s, 6H, -CH3). ESI-MS (MeOH).Observed m/z 271.25 [BPMEN+H+] (z=1); simulated m/z 271.19.

  • 33
  • zinc(II) nitrate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • cis,α-[Zn(N,N'-dimethyl-N,N'-bis(pyridin-2-ylmethyl)-ethane-1,2-diamine)(NO3)2] [ No CAS ]
  • 34
  • copper(II) perchlorate hexahydrate [ No CAS ]
  • [ 1934-75-4 ]
  • [ 136768-57-5 ]
  • [Cu2(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethylenediamine)2(μ-1,5-dicyanamide)]2[ClO4]5[dicyanamide] [ No CAS ]
  • 35
  • [ 136768-57-5 ]
  • iron(II) chloride [ No CAS ]
  • cis-(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-ethanediamine)-dichloroiron(II) [ No CAS ]
  • 36
  • [ 136768-57-5 ]
  • manganese(ll) chloride [ No CAS ]
  • cis-(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-ethanediamine)-dichloromanganese(II) [ No CAS ]
  • 37
  • [ 136768-57-5 ]
  • [ 244250-57-5 ]
  • 38
  • [ 136768-57-5 ]
  • [Fe(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine)(CD3CN)2](triflate)2 [ No CAS ]
  • 39
  • tetrapotassium octacyanomolybdate(IV) dihydrate [ No CAS ]
  • [ 7732-18-5 ]
  • [ 136768-57-5 ]
  • copper(II) perchlorate [ No CAS ]
  • [Cu2(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-diaminoethane)2][Mo(CN)8]*8H2O [ No CAS ]
  • 40
  • [ 136768-57-5 ]
  • nickel dichloride [ No CAS ]
  • [Ni(1,6-bis(2-pyridyl)-2,5-dimethyl-2,5-diazahexane)(H2O)2]Cl2*H2O [ No CAS ]
  • 41
  • [ 41756-81-4 ]
  • [ 136768-57-5 ]
  • C34H37ClN4PRu(1+)*Cl(1-) [ No CAS ]
  • 42
  • α-K8SiW11O39*13H2O [ No CAS ]
  • [ 142-71-2 ]
  • [ 136768-57-5 ]
  • [Cu(N,N′-dimethyl-N,N′-bis(pyridin-2-ylmethyl)-1,2-diaminoethane)(H2O)][SiW12O40{Cu(N,N′-dimethyl-N,N′-bis(pyridin-2-ylmethyl)-1,2-diaminoethane)}] [ No CAS ]
  • 43
  • [ 6959-47-3 ]
  • [ 136768-57-5 ]
  • 44
  • copper(II) perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [Cu(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethylenediamine)(ClO4)]ClO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% In water; for 0.25h;Heating; Copper(II) perchlorate hexahydrate (0.380g, 1.0mmol) was added to Ldpdmen (0.160, 1.0mmol) dissolved in H2O (20mL). This solution was heated for 15min on steam-bath and filtered through Celite and then allowed to crystallize at room temperature. After 2weeks, the blue crystals which separated were collected by filtration, washed with propan-2-ol, followed by ether and air dried (overall yield: 0.340g, 64%). Characterization: Anal. Calc. for C16H22N4Cl2CuO8 (523.43g/mol): C, 36.07; H, 4.16; N, 10.52. Found: C, 35.86; H, 4.13; N, 10.09%. Selected IR bands (KBr, cm-1): ν(Cl-O) (ClO4-) at 1098 (vs). UV-Vis spectrum {λmax, nm (εmax, M-1cm-1)}: in H2O: 634 (251).
  • 45
  • [ 15684-35-2 ]
  • [ 33440-64-1 ]
  • [ 136768-57-5 ]
  • C36H30CoN4O6(1+)*H2O*BF4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% General procedure: Complexes 1-4 were prepared following the method describedpreviously [15]. To a solution of Co(BF4)2·6H2O or Ga(NO3)2·XH2O(0.5 mmol) in 20 mL of methanol was added 2-hydroxy-1,4-naphtoquinone (1.0 mmol). After stirring at room temperature for afew minutes, 10 mL of a methanol solution of L1 or L2 (0.5 mmol)and triethylamine (1.0 mmol) were added. A precipitate, obtainedafter slowevaporation of the solvent,was removed by filtration,washedwith cold methanol and dried under vacuum. Complexes 1-4 thusprepared were all microcrystalline as examined under microscope.They were characterized with elemental analysis and IR spectrameasurements (see Sections 2.4.1-2.4.4 below and Figs. S2-S5) aswell as with 1H NMR spectroscopy (Table S1 and Fig. S1). Althoughthe elemental analysis results for complexes 1 and 2 were somewhatunsatisfactory, no evidence for impurities was found in their 1H NMR spectra
  • 46
  • [ 33440-64-1 ]
  • GaH(2+)*(x)H2O*NO3(1-) [ No CAS ]
  • [ 136768-57-5 ]
  • C34H26GaN4O6(1+)*3H2O*NO3(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% General procedure: Complexes 1-4 were prepared following the method describedpreviously [15]. To a solution of Co(BF4)2·6H2O or Ga(NO3)2·XH2O(0.5 mmol) in 20 mL of methanol was added 2-hydroxy-1,4-naphtoquinone (1.0 mmol). After stirring at room temperature for afew minutes, 10 mL of a methanol solution of L1 or L2 (0.5 mmol)and triethylamine (1.0 mmol) were added. A precipitate, obtainedafter slowevaporation of the solvent,was removed by filtration,washedwith cold methanol and dried under vacuum. Complexes 1-4 thusprepared were all microcrystalline as examined under microscope.They were characterized with elemental analysis and IR spectrameasurements (see Sections 2.4.1-2.4.4 below and Figs. S2-S5) aswell as with 1H NMR spectroscopy (Table S1 and Fig. S1). Althoughthe elemental analysis results for complexes 1 and 2 were somewhatunsatisfactory, no evidence for impurities was found in their 1H NMR spectra
  • 47
  • [ 83-72-7 ]
  • GaH(2+)*(x)H2O*NO3(1-) [ No CAS ]
  • [ 136768-57-5 ]
  • [Ga(bhnq)(L2)]NO3·3H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% General procedure: Complexes 1-4 were prepared following the method describedpreviously [15]. To a solution of Co(BF4)2·6H2O or Ga(NO3)2·XH2O(0.5 mmol) in 20 mL of methanol was added 2-hydroxy-1,4-naphtoquinone (1.0 mmol). After stirring at room temperature for afew minutes, 10 mL of a methanol solution of L1 or L2 (0.5 mmol)and triethylamine (1.0 mmol) were added. A precipitate, obtainedafter slowevaporation of the solvent,was removed by filtration,washedwith cold methanol and dried under vacuum. Complexes 1-4 thusprepared were all microcrystalline as examined under microscope.They were characterized with elemental analysis and IR spectrameasurements (see Sections 2.4.1-2.4.4 below and Figs. S2-S5) aswell as with 1H NMR spectroscopy (Table S1 and Fig. S1). Althoughthe elemental analysis results for complexes 1 and 2 were somewhatunsatisfactory, no evidence for impurities was found in their 1H NMR spectra
  • 48
  • [ 17084-13-8 ]
  • iron(III) chloride [ No CAS ]
  • [ 136768-57-5 ]
  • [FeIII((N,N'-dimethyl-N,N'-bis-2-pyridinylmethyl)-1,2-ethanediamine)(Cl)2](PF6) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20℃; [FeIII(BPMEN)(Cl)2](PF6) [2], was prepared by adding drop-wise a 10 mL solution of iron(III) chloride (FeCl3) (288 mg) to a10 mL solution of N,N-dimethyl-N,N-bis-2-pyridinylmethyl)-1,2-ethanediamine (BPMEN) (480 mg) in methanol under stirring at room temperature. The complex precipitated as a yellow solid upon addition of a 5 mL solution of potassium hexafluorophosphate (1 g) in methanol. Recrystallization by ether diffusion in acetonitrile yielded yellow crystals of the desired complex. HR ESI-MS analysis for [FeIII(BPMEN)(Cl)2]+: m/z 396.0579; calculated: m/z 396.0566. Elemental analysis: calculated for C16H24Cl2F12FeN4P2, C 27,89%, H3.51%, N 8.13%. Found, C 27.83%, H 3.25%, N 8.25%.
  • 49
  • [ 80937-33-3 ]
  • [ 127-09-3 ]
  • [ 136768-57-5 ]
  • iron(III) perchlorate [ No CAS ]
  • diiron(III)(μ-oxo)(μ-acetate)bis(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine) perchlorate [ No CAS ]
  • 50
  • iron(III) chloride [ No CAS ]
  • [ 80937-33-3 ]
  • [ 136768-57-5 ]
  • [Fe(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-diaminoethane)(μ-O)FeCl3] [ No CAS ]
  • 51
  • [ 17084-13-8 ]
  • iron(III) chloride [ No CAS ]
  • [ 136768-57-5 ]
  • [FeIII((N,N'-dimethyl-N,N'-bis-2-pyridinylmethyl)-1,2-ethanediamine)(chloride)2](hexafluorophosphate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; at 20℃; [2], was prepared by adding dropwise a 10mL solution of iron(III) chloride (FeCl3) (288mg) to a 10mL solution of N,N′-dimethyl-N,N′-bis-2-pyridinylmethyl)-1,2-ethanediamine (BPMEN) (480mg) in methanol under stirring at room temperature. The complex precipitated as a yellow solid upon addition of a 5mL solution of potassium hexafluorophosphate (1g) in methanol. Recrystallization by ether diffusion in acetonitrile yielded yellow crystals of the desired complex. HR ESI-MS analysis for [FeIII(BPMEN)(Cl)2]+: m/z 396.0579; calculated: m/z 396.0566. Elemental analysis: calculated for C16H24Cl2F12FeN4P2, C 27,89%, H 3.51%, N 8.13%. Found, C 27.83%, H 3.25%, N 8.25%.
  • 52
  • iron(II) perchlorate hexahydrate [ No CAS ]
  • [ 3425-46-5 ]
  • [ 136768-57-5 ]
  • [Fe(N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-1,2-ethanediamine)(NCSe)2] [ No CAS ]
  • 53
  • iron(II) perchlorate hexahydrate [ No CAS ]
  • [ 3425-46-5 ]
  • [ 136768-57-5 ]
  • [Fe(N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-1,2-ethanediamine)(NCSe)2] [ No CAS ]
  • [Fe(N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-1,2-ethanediamine)(NCSe)2] [ No CAS ]
  • 54
  • iron(II) perchlorate hexahydrate [ No CAS ]
  • [ 3425-46-5 ]
  • [ 136768-57-5 ]
  • [Fe(N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-1,2-ethanediamine)(NCSe)2] [ No CAS ]
  • 55
  • [ 7681-65-4 ]
  • [ 136768-57-5 ]
  • C16H22N4*Cu(1+)*I(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 20℃; for 2h;Inert atmosphere; CuI (0.25 mmol) and BPMEN (0.25 mmol) were added to CH3CN (1 mL) in an Ar atmosphere, and the mixture was stirred at room temperature for 2 h. After the reaction, the solvent was removed under vacuum to yield a Cu(BPMEN)I complex, which was then washed with CH3CN and diethyl ether and dried under vacuum. HRMS (ESI-MS) calcd for C16H22CuN4 [M -I]+: 333.1121; found: 333.1135. Anal. calcd for C16H22CuN4I·0.7MeCN: C 42.84%, H 5.12%, N 13.38%; found C 42.69%, H4.96%, N 13.45%.
  • 56
  • iron(III) perchlorate decahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • diiron(III)(μ-oxo)(μ-hydroxo)bis(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine) perchlorate [ No CAS ]
  • 57
  • nickel(II) perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [Ni(N,N’-dimethyl-N,N’-bis(pyridin-2-ylmethyl)-1,2-diaminoethane)(H2O)2](ClO4)2 [ No CAS ]
  • 58
  • manganese(II) triflate [ No CAS ]
  • [ 136768-57-5 ]
  • [Mn(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-ethanediamine)(OTf)2] [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In acetonitrile; at 20℃; for 15h; According to ref [29], Mn(OTf)2 (0.875 g, 2.4 mmol) was added to a solution of L (0.54g, 2 mmol) in 3 mL of acetonitrile. The mixture was stirred at room temperature for 15 hand the solvent was removed under vacuum. The light grey powder obtained was washedtwice with diethyl ether and after recrystallization by diffusion of diethyl ether into a solutionof the product in acetonitrile, (L)Mn(OTf)2 (0.85 g, 68 % yield) was obtained as awhite powder.Anal. Calc. for C18H22F6MnN4O6S2: C, 34.68; H, 3.56; N, 8.99. Found: C, 34.68; H, 3.42;N, 8.95.
  • 59
  • [ 15418-29-8 ]
  • [ 136768-57-5 ]
  • [Cu(N1,N2-dimethyl-N1,N2-bis(pyridin-2-ylmethyl)ethane-1,2-diamine)][BF4]2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With acetonitrile; at -40 - 20℃; for 24h;Inert atmosphere; Solid [Cu(CH3CN)4][BF4]2 (74 mg, 0.18 mmol) was added to a solution of LH (51 mg, 0.18 mmol) in 5 mL ofCH3CN. The dark blue solution was stirred at 25 C for 0.5 h then 5 mL of Et2O was added to precipitatethe complex. The supernatant was decanted and resulting crude blue oil was triturated with toluene toachieve a dark blue powder. The crude powder was redissolved in ca. 1 mL of CH3CN and layered with4 mL of THF. After 1 day at -40 C, dark blue solid was isolated by filtration and washed with 2 × 4 mLTHF (96 mg, 94% yield).
  • 60
  • [ 136768-57-5 ]
  • [Cu(N1,N2-dimethyl-N1,N2-bis(pyridin-2-ylmethyl)ethane-1,2-diamine)][BF4] [ No CAS ]
  • 61
  • [ 136768-57-5 ]
  • [ 133902-54-2 ]
  • cobalt(II) perchlorate hexahydrate [ No CAS ]
  • [CoIII(N,N′-dimethyl-N,N′-bis(pyridin-2-ylmethyl)ethylenediamine)((E)-1-phenyl-1H-1,2,3-triazole-4-carbaldehydeoxime)](ClO4)2*H2O [ No CAS ]
  • 62
  • nickel(II) chloride hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • Ni(N,N′‑dimethyl‑N,N′‑bis(pyridine‑2‑ylmethyl)‑1,2‑diaminoethane)Cl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% In methanol; The complex 1 was prepared by following a published procedure(Singh et al. 2017).The ligand BPMEN (0.238 g,1 mmol) dissolved in methanol (4 mL) was added dropwiseto a stirring solution of NiCl2.6H2O(0.27 g, 1 mmol) inmethanol (4 mL). Blue green solution was obtained immediatelyupon addition. Evaporation of solvent gave a blue greencolor powder (0.396 g, Yield 99%). ESI-MS (in CH3OH)for [Ni(BPMEN)Cl]+ (z = 1) m/z 363.13 (experimental) m/z363.09 (theoretical) and for [Ni(BPMEN)]2+ (z = 2) m/z164.21 (experimental) m/z 164.06 (theoretical). Elementalanalysis Calculated (%): C 45.37, H 6.27, N 12.45 Found(%): C 45.18, H 5.82, N 13.3. UV-Vis λmax in nm (ε in M-1cm-1) in MeOH at RT: 603 (15), 986 (26).
63% The complex was prepared by following a published procedure[21]. A filtered solution of NiCl26H2O (0.238 g, 1 mmol) in water(1 mL) was diluted with ethanol (2 mL) and heated for 15 min at70 C. After 15 min., the solution was mixed with a solution ofligand L1 (0.270 g, 1 mmol) in ethanol (1 mL). The resulting darkblue solution was kept inside the diethyl ether jar for ether vapordiffusion to produce blue green crystals (0.250 g, 0.625 mmol,Yield 63%). ESI-MS (in CH3OH): Observed m/z 363.25 [Ni(L1) Cl]+(z = 1), theoretical 363.09. UV-vis (in MeOH) kmax ( M1 cm1):601 (15), 981 (28).
  • 63
  • copper(II) perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • C16H22ClCuN4O4(1+)*ClO4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% In methanol; for 0.166667h; Complex 4 was prepared by similar published procedure [20].Addition of a solution of Cu(ClO4)26H2O(0.371 g, 1 mmol) inmethanol (5 mL) to another a solution of ligand L1 (0.270 g,1 mmol) in 10 mL methanol followed by 10 min stirring led tothe formation of dark blue precipitates. The supernatant liquidwas taken out and dark blue precipitates were dried under vacuum.Recrystallization from a mixture of hexane and acetonitrileby vapor diffusion afforded blue prism shaped crystals (0.308 g,0.578 mmol, Yield 58%). ESI-MS (in CH3CN). Observed m/z 432.12[Cu(L1) ClO4]+ (z = 1) Theoretical- 432.06; observed 333.23[Cu(L1)]+ (z = 1) theoretical 333.11. Anal. Calcd (%) for C16H22Cl2CuN4-O8: C 36.07, H 4.16, N 10.52, Cl 13.31. Found (%): C 36.31, H 4.25, N10.48, Cl 13.12. UV-vis (in MeCN) kmax in nm ( M1 cm1): 624(450).
58% In methanol; at 20℃; for 0.5h; The ligand BPMEN (0.271 g, 1.00 mmol) was dissolved in 10 mLMeOH and combined with a 5 mL MeOH solution containing Cu(II)(ClO4)2·6H2O (0.370 g, 1.00 mmol) and stirred for 30 min. The combined solution was allowed to slowly evaporate to produce[(BPMEN)Cu(ClO4)2]. (Yield: 0.307 g, 0.576 mmol, 58%) UV-vis(MeCN) λmax 624 nm (ε = 260M-1 cm-1). ESI-MS (MeCN). Observed m/z 333.11 [(BPMEN)Cu] (z=1), 432.06 [(BPMEN)Cu(ClO4)] (z=1); simulated m/z 333.11, 432.06.
  • 64
  • [ 67-56-1 ]
  • [ 83-72-7 ]
  • iron(III) perchlorate hydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [Fe(2,2'-bis(3-hydroxy-1,4-naphthoquinone))(N,N'-dimethyl-N,N'-bis(pyridin-2-ylmethyl)ethylenediamine)]ClO4*CH3OH [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With triethylamine; for 0.5h; General procedure: To a 20 mL methanol solution of Fe(NO3)39H2O or Fe(ClO4)3xH2O (0.5 mmol) was added 2-hydroxy-1,4-naphthoquinone (1.0 mmol) followed by 10 mL of a methanol solution of H2L1 or H2L2 (0.5 mmol) and triethylamine (1.0 mmol). After 30 min, a dark precipitate was removed by filtration, washed withcold methanol and dried under vacuum.
  • 65
  • iron(II) perchlorate monohydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [ 76-93-7 ]
  • [(N1,N2-dimethyl-N1,N2-bis(2-pyridylmethyl)ethane-1,2-diamine)FeII(benzilate)](ClO4) [ No CAS ]
  • 66
  • nickel(II) perchlorate hexahydrate [ No CAS ]
  • [ 143-66-8 ]
  • [ 136768-57-5 ]
  • [ 75-05-8 ]
  • [Ni(N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)ethylenediamine)(CH3CN)2](BPh4)2 [ No CAS ]
  • 67
  • [ 333-20-0 ]
  • [ 136768-57-5 ]
  • Ni(II) precursor [ No CAS ]
  • C18H22N6NiS2 [ No CAS ]
  • 68
  • [ 136768-57-5 ]
  • [ 25895-60-7 ]
  • Ni(II) precursor [ No CAS ]
  • C18H28B2N6Ni [ No CAS ]
  • 69
  • [ 136768-57-5 ]
  • Fe(III)(N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-ethane-1,2-diamine)PF6 [ No CAS ]
  • 70
  • [ 136768-57-5 ]
  • [Fe(II)(N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-ethane-1,2-diamine)(MeCN)2][SbF6]2 [ No CAS ]
  • 71
  • iron(II) chloride tetrahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [ 1271844-30-4 ]
  • 72
  • [Cu(N,N′‑dimethyl‑N,N′‑bis‑(pyridine‑2‑ylmethyl)‑1,2‑diaminoethane)(ClO4)2] [ No CAS ]
  • [ 136768-57-5 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; triethylamine; In acetonitrile; at 20℃; General procedure: The reactions of 1 and 2 with H2O2 were performed in a UV-Vis cell under anaerobic conditions. Solutions of 1 and 2 were prepared in anhydrous acetonitrile (2 mM) and kept at room temperature. To this solution, triethylamine (NEt3, 10 equivalents) and H2O2 (10 equivalents)were added using a gas tight syringe.
  • 73
  • iron(II) perchlorate hexahydrate [ No CAS ]
  • [ 490-79-9 ]
  • [ 136768-57-5 ]
  • [(N1,N2-dimethyl-N1,N2-bis(2-pyridylmethyl)ethane-1,2-diamine)FeII(2,5-dihydroxybenzoate)](ClO4) [ No CAS ]
  • 74
  • iron(II) perchlorate hexahydrate [ No CAS ]
  • [ 31519-22-9 ]
  • [ 136768-57-5 ]
  • [(N1,N2-dimethyl-N1,N2-bis(2-pyridylmethyl)ethane-1,2-diamine)FeII(1,4-dihydroxy-2-naphthoate)](ClO4) [ No CAS ]
  • 75
  • iron(II) perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [ 86-48-6 ]
  • [(N1,N2-dimethyl-N1,N2-bis(2-pyridylmethyl)ethane-1,2-diamine)FeII(1-hydroxy-2-naphthoate)](ClO4) [ No CAS ]
  • 76
  • iron(II) perchlorate hexahydrate [ No CAS ]
  • [ 2612-02-4 ]
  • [ 136768-57-5 ]
  • [(N1,N2-dimethyl-N1,N2-bis(2-pyridylmethyl)ethane-1,2-diamine)FeII(5-methoxysalicylate)](ClO4) [ No CAS ]
  • 77
  • iron(III) trifluoromethanesulfonate [ No CAS ]
  • [ 136768-57-5 ]
  • C16H22N4*Fe(3+)*3CF3O3S(1-) [ No CAS ]
  • 78
  • iron(II) trifluoromethanesulfonate dihydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [Fe(N,N'-bis-(2-pyridylmethyl)-N,N'-dimethyl-1,2-ethylenediamine)(OTf)2] [ No CAS ]
  • 79
  • iron(II) perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [ 25895-60-7 ]
  • C18H28B2FeN6 [ No CAS ]
  • 80
  • cobalt (II) perchlorate hexahydrate [ No CAS ]
  • lithium perchlorate [ No CAS ]
  • [ 7782-50-5 ]
  • [ 136768-57-5 ]
  • [CoCl2(N,N′-dimethyl-N,N′-bis(pyridin-2-ylmethyl)ethylenediamine)]ClO4 [ No CAS ]
  • 81
  • copper(II) perchlorate hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • [Cu(N,N'-bis(2-pyridylmethyl)-1,2-ethanediamine)](ClO4)2 [ No CAS ]
  • 82
  • iron(III) chloride hexahydrate [ No CAS ]
  • [ 136768-57-5 ]
  • C16H22Cl2FeN4(1+)*Cl4Fe(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% In acetonitrile; at 20℃; for 15h; FeCl3,6H2O (1.08 g, 4 mmol) was added to a solution of L (0.54 g, 2 mmol) in 5 mL ofacetonitrile. After 15 min, a red precipitate appeared and the mixture was stirred for 15 hat room temperature. After filtration of the red solid recrystallization in CH3CN afforded[(L)FeCl2](FeCl4) (0.93 g, 73% yield) as a red solid.Anal. Calc. for C16H22Cl6Fe2N4: C, 32.31; H, 3.73; N, 9.42. Found: C, 32.39; H, 3.16; N,9.33.
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