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CAS No. : | 220593-43-1 | MDL No. : | N/A |
Formula : | C21H24N6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UAVXIWSFNFWPAX-UHFFFAOYSA-N |
M.W : | 360.46 | Pubchem ID : | 5233007 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
92% | Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene In N,N-dimethyl-formamide at 20℃; for 20h; | |
64% | Stage #1: 1H-imidazole With sodium hydroxide In acetonitrile at 20℃; for 2h; Stage #2: 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene In acetonitrile at 50 - 60℃; for 24h; | 4.3.2. Synthesis of 1,3,5-Tris(imidazole-1-yl-methyl)-2,4,6-trimethylbenzene (A) To a mixture of imidazole (874 mg, 12.8 mmol) in acetonitrile (50 mL), in a 100 mL round-bottomedflask, NaOH (1.029 g, 25.72 mmol) was added and stirred at room temperature for two hours.1,3,5-Tris(bromomethyl)-2,4,6-trimethylbenzene (1.416 g, 4.000 mmol) in acetonitrile (20 mL) wasadded to the reaction mixture and refluxed for 24 h at 50-60 °C. The reaction mixture was monitoredwith TLC and after completion, the solvent was removed by rotary evaporation, the residue wasdissolved in water (100 mL) and extracted with methylene chloride (30 mL 5). The organic layerswere combined, dried over anhydrous MgSO4, filtered and purified by flash column chromatography(CH2Cl2/MeOH = 5/1) to give the desired product as a white solid. Recrystallization in ethyl acetateproduced clear block like crystals 64% yield. mp 214-215 °C (Lit value 226-227 °C) [31]; 1H-NMR(δH; CDCl3, 400 MHz) δ 7.31 (s, 3H), 7.07 (s, 3H), 6.75 (s, 3H), 5.24 (s, 6H) 2.32 (s, 9H). |
In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In acetonitrile at 68℃; for 96h; | |
87% | In acetone at 25℃; for 168000h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile for 35h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | In water; acetonitrile addn. of ligand (in MeCN/water=9:1) to mixt. of Cu-salt and triamine (inMeCN) with stirring, stirring for 5 min at room temp.; filtration, crystn. on Et2O diffusion; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In water; acetonitrile addn. of ligand (in MeCN/water=9:1) to Cu-complex (in MeCN) with stirring, stirring for 5 min at room temp.; filtration, crystn. on Et2O diffusion; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | In water; acetonitrile soln of ligand in 1:1 CH3CN-H2O mixt. added to soln. of Pd-complex in CH3CN at room temp., stirred for 1 h; mixt. filtered, filtrate stand at ambient temp. for a month; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol 2 equiv. of ligand; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | In water; acetonitrile soln. ligand in MeCN was layered over aq. soln. Ag(NH3)2N3; crystals were filtered; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol by spontaneous assembly from (C(CH3)C(CH2(NCHN(CH)2)))3 ligand and copper(II) acetate in methanol soln.; according to H.-K. Liu, W.-Y. Sun, W.-X. Tang, T. Yamamoto, Ueyama, Inorg. Chem. 38(1999) 6313; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | In ethanol EtOH soln. Zn(OAc)2*2H2O was added slowly to soln. ligand in EtOH and stirred for 5 h at room temp.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | In methanol; water MeOH soln. of ligand and water soln. of MnSO4*H2O mixed, allowed to stand in air at room temp. for several days; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In methanol; water exclusion of light; soln. of the benzene derivative in CH3OH carefully layered over aq. soln. of Ag complex; crystn. within several weeks; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In methanol; water exclusion of light; soln. of the benzene derivative in CH3OH carefully layered over aq. soln. of Ag complex; crystn. within several weeks; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In ethanol; water soln. of ligand in EtOH was layered on soln. of Zn(ClO4)2*6H2O in water,crystn. after several weeks; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In ethanol; water soln. of ligand in EtOH was layered over soln. of CdSO4*2.7H2O in water; crystn. after several weeks; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In methanol; water (in the dark); a MeOH soln. of ligand added to an aq. soln. of Ag complex (prepd. from AgClO4*H2O and sodium salicylate), stirred for 30 min; filtered, crystd. for days at room temp.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In water; acetonitrile aq. soln. Mn(OAc)2*4H2O and NaN3 was refluxed and stirred for 8 h, filtered and cooled to room temp., soln. ligand in MeCN was layered carefullyover aq. soln. at room temp., 2 weeks; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | In methanol; water aq. soln. Mn(OAc)2*4H2O and K2C2O4 was refluxed and stirred for 8 h, filtered and cooled to room temp., soln. ligand in MeOH was layered carefully over aq. soln. at room temp., 3 weeks; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In methanol; water aq. soln. ZnO and H2mal was refluxed and stirred for 8 h, soln. was filtered and cooled to room temp., soln. titmb in MeOH was layered over aq. soln. at room temp., 3 weeks; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | In water High Pressure; Cu-salt:N-compd. molar ratio was 3:2, teflon-lined autoclave, 150 °C for 72 h; cooling to room temp., crystals were collected, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In water High Pressure; Cu-salt:N-compd.:NaN3 molar ratio was 1:1:2, teflon-lined autoclave, 100°C for 72 h; cooling to room temp., crystals were collected, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | In water High Pressure; Cu-salt:N-compd. molar ratio was 2:1, teflon-lined autoclave, 100 °C for 72 h; cooling to room temp., crystals were collected, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In methanol; acetonitrile soln. of ligand in MeOH added to MeCN soln. of AgPF6 at room temp., stirred for 1 h; filtered, allowed to stand for 1 wk; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | In methanol soln. of ligand in MeOH added to MeOH soln. of AgSbF6 at room temp., stirred for 1 h; filtered, allowed to stand for 1 wk; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In N,N-dimethyl-formamide High Pressure; heating mixt. of tungsten compd., imidazole deriv. and DMF at 120°C for 24 h; cooling to room temp. at rate 0.05°C/min, isolation of crystals, washing with CH3CN and diethyl ether, drying in air, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | In ethanol; water High Pressure; CdCl2, 1,3,5-tris(imidazol-1-ylmethyl)-2,4,6-trimethylbenzene, 1,3,5-benzenetricarboxylic acid placed in autoclave with H2O and EtOH 3:1, heatedto 160°C in 4 h, kept for 3 d, cooled to room temp. at 2.5.degre e.C/h; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | In ethanol; water High Pressure; Zn(NO3)2, 1,3,5-tris(imidazol-1-ylmethyl)-2,4,6-trimethylbenzene, 1,3,5-benzenetricarboxylic acid placed in autoclave with H2O and EtOH 3:1, heated to 160°C in 4 h, kept for 3 d, cooled to room temp. at 2.5°C/h; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With sodium hydroxide In water at 180℃; for 72h; Sealed tube; | 2.2. Synthesis of Zn2(titmb)(BTC)Cl (1) A mixture containing ZnCl2 (27.2 mg, 0.2 mmol), H3BTC(21.0 mg, 0.1 mmol), titmb (36.0 mg, 0.1 mmol) and NaOH(12.0 mg, 0.3 mmol) in 15 ml deionized water was sealed in a25 ml Teflon lined stainless steel container and heated at 180 °C for 3 days. Colorless cubic crystals of 1 were collected by filtrationand washed with water and ethanol several times with a yield of71%. Anal. Calc. for C30H27ClN6O6Zn2 (733.77): C, 49.10; H, 3.71;N, 11.45. Found: C, 49.01; H, 3.74; N, 11.42%. IR (KBr/pellet)/cm-1: 3415 (br), 3132 (w), 2819 (w), 1611 (s), 1577 (s), 1521 (s),1443 (m), 1385 (m), 1295 (m), 1251 (m), 1109 (m), 1093 (m),1075 (s), 1012 (m), 946 (m), 865 (w), 817 (w), 772 (m), 759 (m),675 (w), 641 (m). |
39% | In ethanol; water High Pressure; ZnCl2, 1,3,5-tris(imidazol-1-ylmethyl)-2,4,6-trimethylbenzene, 1,3,5-benzenetricarboxylic acid placed in autoclave with H2O and EtOH 3:1, heatedto 160°C in 4 h, kept for 3 d, cooled to room temp. at 2.5.degre e.C/h; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In hydrogenchloride; water High Pressure; into Pyrex glass tube added CdSO4*2.67H2O, aq. HCl, ligand and water andtube sealed; tube heated to 150°C for 2 d and then cooled down a t rate 5°C/h; crystals washed with ethanol and dried in air; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | In hydrogenchloride; methanol High Pressure; into Pyrex glass tube added CdSO4*2.67H2O, aq. HCl, ligand and methanol and tube sealed; tube heated to 150°C for 2 d and then cooled down at rate 5°C/h; crystals washed with ethanol and dried in air; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In hydrogenchloride; ethanol High Pressure; into Pyrex glass tube added CdSO4*2.67H2O, aq. HCl, ligand and ethanol and tube sealed; tube heated to 150°C for 2 d and then cooled downat rate 5°C/h; crystals washed with ethanol and dried in air; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In acetonitrile at 80℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol mixt. Ln(NO3)3*6H2O, ligand, MeOH , and HC(OEt)3 was refluxed for 2 h; soln. was filtered, filtrate was allowed to stand in desiccator at room temp. for several days; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol mixt. Ln(NO3)3*6H2O, ligand, MeOH , and HC(OEt)3 was refluxed for 2 h; soln. was filtered, filtrate was allowed to stand in desiccator at room temp. for several days; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol mixt. Ln(NO3)3*6H2O, ligand, MeOH , and HC(OEt)3 was refluxed for 2 h; soln. was filtered, filtrate was allowed to stand in desiccator at room temp. for several days; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol mixt. Ln(NO3)3*6H2O, ligand, MeOH , and HC(OEt)3 was refluxed for 2 h; soln. was filtered, filtrate was allowed to stand in desiccator at room temp. for several days; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol mixt. Ln(NO3)3*6H2O, ligand, MeOH , and HC(OEt)3 was refluxed for 2 h; soln. was filtered, filtrate was allowed to stand in desiccator at room temp. for several days; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol mixt. Ln(NO3)3*6H2O, ligand, MeOH , and HC(OEt)3 was refluxed for 2 h; soln. was filtered, filtrate was allowed to stand in desiccator at room temp. for several days; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In acetonitrile Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: sodium tetrafluoroborate / ethanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With NaOH In water High Pressure; equimol., pH adjusted to 5.0 (aq. NaOH), heated to 150°C for 3 d; cooled to room temp.; elem. anal., TGA; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.9% | Stage #1: cobalt(II) nitrate hexahydrate; 4,4′-(((5-((4-(hydroxy-l2-methoxy)phenoxy)methyl)-2,4,6-trimethyl-1,3-phenylene)bis(methylene))bis(oxy))dibenzoic acid; water; 1,3,5-tris(N-imidazolylmethyl)-2,4,6-trimethylbenzene With hydrogenchloride at 100℃; for 72h; High pressure; Stage #2: N,N-dimethyl-formamide | 2.3.2 [Co3L2(titb)2]·2H2O·2.5DMF (1) To the solution of H3L (0.030 g, 0.052 mmol) and titb (0.018 g, 0.050 mmol) in 4 mL of N,N-dimethylformamide (DMF) was added the solution of Co(NO3)2·6H2O (0.029 g, 0.10 mmol) in 2 mL of H2O to give a turbid mixture. Two drops of aqueous HCl (1:1 volume) were added to the mixture and a clear solution with pH ≈5 was obtained. The solution was transferred into a vial, which was then sealed and heated at 100 °C for 3 days. The vial was then allowed to cool down to room temperature. Blue crystals (0.033 g) were obtained by filtration and washed with DMF and CH2Cl2 three times each, respectively. Yield: 58.9% (based on titb). Anal. Calc. for C115.5H123.5Co3N14.5O22.5: C, 61.61; H, 5.53; N, 9.02. Found: C, 61.74; H, 5.47; N, 8.57%. FT-IR (KBr, cm-1): 3394 m, b, 3119 m, 2925 m, 2353 m, 1668 s, 1598 s, 1552 s, 1505 s, 1362 s, 1296 s, 1229 s, 1163 s, 1097 s, 987 s, 854 s, 778 s, 691 m, 651 s, 611 m, 508 w, 422 w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.3% | Stage #1: zinc(II) nitrate hexahydrate; 4,4′-(((5-((4-(hydroxy-l2-methoxy)phenoxy)methyl)-2,4,6-trimethyl-1,3-phenylene)bis(methylene))bis(oxy))dibenzoic acid; water; 1,3,5-tris(N-imidazolylmethyl)-2,4,6-trimethylbenzene With hydrogenchloride at 100℃; for 72h; High pressure; Stage #2: N,N-dimethyl-formamide | 2.3.3 [Zn3L2(titb)2]·2H2O·2.5DMF (2) Colorless crystals (0.028 g) of 2 were obtained by following the same procedure as 1 with the replacement of Co(NO3)2·6H2O with Zn(NO3)2·6H2O and crystallization at 120 °C. Yield: 48.3% (based on titb). Anal. Calc. for C115.5H123.5Zn3N14.5O22.5: C, 61.09; H, 5.48; N, 8.94. Found: C, 61.54; H, 5.43; N, 8.83%. FT-IR (KBr, cm-1): 3636 w, 3397 m, b, 3116 m, 2917 m, 1667 s, 1601 s, 1562 s, 1360 s, 1294 m, 1235 s, 1168 s, 1099 s, 1026 m, 984 s, 942 m, 858 s, 785 s, 691 m, 653 s, 621 w, 604 w, 562 w, 503 w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.7% | Stage #1: cadmium(II) nitrate tetrhydrate; 4,4′-(((5-((4-(hydroxy-l2-methoxy)phenoxy)methyl)-2,4,6-trimethyl-1,3-phenylene)bis(methylene))bis(oxy))dibenzoic acid; water; 1,3,5-tris(N-imidazolylmethyl)-2,4,6-trimethylbenzene With hydrogenchloride at 100℃; for 72h; High pressure; Stage #2: N,N-dimethyl-formamide | 2.3.4 [Cd3L2(titb)2]·2H2O·2.5DMF (3) Colorless crystals (0.028 g) of 2 were obtained by following the same procedure as 1 with the replacement of Co(NO3)2·6H2O with Zn(NO3)2·6H2O and crystallization at 120 °C. Yield: 48.3% (based on titb). Anal. Calc. for C115.5H123.5Zn3N14.5O22.5: C, 61.09; H, 5.48; N, 8.94. Found: C, 61.54; H, 5.43; N, 8.83%. FT-IR (KBr, cm-1): 3636 w, 3397 m, b, 3116 m, 2917 m, 1667 s, 1601 s, 1562 s, 1360 s, 1294 m, 1235 s, 1168 s, 1099 s, 1026 m, 984 s, 942 m, 858 s, 785 s, 691 m, 653 s, 621 w, 604 w, 562 w, 503 w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In butan-1-ol Reflux; | To a round bottom flask was added 0.72 g (2 mmol) TITMB, 1.32 g (6 mmol) 2- (bromomethyl) naphthalene and 10 ml butyl alcohol. The solution was refluxed overnight during which time a precipitate formed. The solid was filtered and washed with THF to afford 1.32 g of 1 ,1M"-((2,4,6-trimethylbenzene-1 ,3,5- triyl)tris(methylene))tris(3-(naphthalen-2-ylmethyl)-1 H-imidazolium) tribromide as a yellowish-white solid. 1H NMR (DMSO-d6): δ 2.35, 5.63, 5.67, 7.53, 7.54, 7.72, 7.79, 7.86, 7.89, 7.96, 9.66. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In acetonitrile for 72h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium hydroxide at 180℃; for 72h; Sealed tube; | 2.3. Synthesis of Zn3(titmb)(BTC)2(H2O) (2) The preparation of 2 was similar to that of 1 except thatZn(NO3)26H2O was used instead of ZnCl2 as metal salt. Colorlessblock crystals of 2 were collected in a 67% yield. Anal. Calc. for C39-H32N6O13Zn3: C, 47.37; H, 3.26; N, 8.50. Found: C, 47.32; H, 3.31; N,8.46%. IR data (KBr, cm1): 3441 (w), 3151 (w), 2823 (w), 1605 (s),1561 (s), 1519 (m), 1444 (m), 1409 (m), 1387 (s), 1276 (m), 1111(m), 1089 (m), 1033 (w), 951 (w), 827 (w), 756 (s), 731 (s), 652(w), 537 (w). A mixture containing ZnCl2 (27.2 mg, 0.2 mmol), H3BTC(21.0 mg, 0.1 mmol), titmb (36.0 mg, 0.1 mmol) and NaOH(12.0 mg, 0.3 mmol) in 15 ml deionized water was sealed in a25 ml Teflon lined stainless steel container and heated at 180 °C for 3 days. Colorless cubic crystals of 1 were collected by filtrationand washed with water and ethanol several times with a yield of71%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | In toluene; at 160℃; for 48.0h; | A mixture of <strong>[14285-68-8]Re2(CO)10</strong> (101.1mg, 0.1549mmol), H-BENZ (36.3mg, 0.3072mmol) and timz (36.9mg, 0.1023mmol) in toluene (10mL) in a Teflon flask was placed in a steel bomb. The bomb was kept in an oven maintained at 160C for 48h and then cooled to 25C. Pale yellow coloured powder of 3 (67.5mg, 42%) was obtained. The powder was filtered and washed with toluene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | In toluene; at 160℃; for 48.0h; | A mixture of <strong>[14285-68-8]Re2(CO)10</strong> (100.8mg, 0.1544mmol), H-IMZ (20.9mg, 0.3069mmol) and timz (36.9mg, 0.1023mmol) in toluene (10mL) in a Teflon flask was placed in a steel bomb. The bomb was kept in an oven maintained at 160C for 48h and then cooled to 25C. Pale yellow coloured powder of 2 (61.9mg, 43%) was obtained. The compound was filtered and washed with toluene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | at 160℃; for 72h; Autoclave; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With lithium hydroxide monohydrate In water at 140℃; for 72h; Autoclave; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With sodium hydroxide at 150℃; for 72h; Autoclave; | 2.2.2 Synthesis of 2 A mixture of CoCl2·6H2O (0.24 g, 1.0 mmol), H2L1 (0.17 g, 1.0 mmol), titb (0.36 g, 1.0 mmol) and water (8 ml) was placed in a 25-ml Teflon-lined stainless steel vessel. The pH value was then adjusted to 5.0 with 1 M NaOH solution and the mixture was heated at 150 °C for 3 days, and then the reaction system was cooled to room temperature. Purple crystals were obtained in yield (based on Co): 49%. Elemental Anal. Calc. for 2: C, 51.87; H, 6.04; N, 11.71. Found: C, 51.98; H, 6.10; N, 11.69%. Selected IR (KBr): ν (cm-1) = 3430 (s), 3118 (m), 2924 (m), 1596 (s),1518(m), 1400 (s), 1277 (s), 1224 (s), 1090 (s), 1019 (m), 949 (m), 851 (m), 767 (m), 658 (s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With sodium hydroxide at 150℃; for 72h; Autoclave; | 2.2.2 Synthesis of 2 General procedure: A mixture of CoCl2·6H2O (0.24 g, 1.0 mmol), H2L1 (0.17 g, 1.0 mmol), titb (0.36 g, 1.0 mmol) and water (8 ml) was placed in a 25-ml Teflon-lined stainless steel vessel. The pH value was then adjusted to 5.0 with 1 M NaOH solution and the mixture was heated at 150 °C for 3 days, and then the reaction system was cooled to room temperature. Purple crystals were obtained in yield (based on Co): 49%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With sodium hydroxide at 150℃; for 72h; Autoclave; | 2.2.2 Synthesis of 2 General procedure: A mixture of CoCl2·6H2O (0.24 g, 1.0 mmol), H2L1 (0.17 g, 1.0 mmol), titb (0.36 g, 1.0 mmol) and water (8 ml) was placed in a 25-ml Teflon-lined stainless steel vessel. The pH value was then adjusted to 5.0 with 1 M NaOH solution and the mixture was heated at 150 °C for 3 days, and then the reaction system was cooled to room temperature. Purple crystals were obtained in yield (based on Co): 49%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | at 150℃; for 72h; Autoclave; | 2.2.1 Synthesis of 1 A mixture of CdSO4·8/3H2O (0.26 g, 1.0 mmol), titb (0.36 g, 1.0 mmol), a small amount of HNO3 and water (8 ml) was placed in a 25-ml Teflon-lined stainless steel vessel. The mixture was heated at 150 °C for 3 days, and then the reaction system was cooled to room temperature. Colorless crystals were obtained in yield (based on Cd): 42%. Elemental Anal. Calc. for 1: C, 36.23; H, 3.62; N, 14.08. Found: C, 36.28; H, 3.69; N, 14.01%. Selected IR (KBr): ν (cm-1) = 3422 (s), 3101 (m), 2957 (m), 2880 (m), 1596 (s), 1560 (s), 1522 (s), 1425 (s), 1239 (s), 1105 (s), 1086 (s), 724 (s), 684 (s), 655 (m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With hydrogenchloride In water at 20 - 170℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With hydrogenchloride at 20 - 150℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With hydrogenchloride; lead(II) iodide In water at 20 - 170℃; for 144h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With hydrogenchloride In water at 20 - 170℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With sodium hydroxide In water at 180℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With lithium hydroxide monohydrate In water at 140℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With sodium hydroxide In water at 160℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With water In water at 140℃; for 72h; Sealed tube; | Synthesis of Complex 1 A mixture containing Co(NO3)26H2O (58.2 mg,0.2 mmol), H2BPDA (27.0 mg, 0.1 mmol), titmb(36.0 mg, 0.1 mmol) and LiOHH2O (8.4 mg, 0.2 mmol)in 15 ml deionized water was sealed in a 25 ml Teflonlined stainless steel container and heated at 140 C for3 days. Purple platelet crystals of 1 were collected by filtrationand washed with water and ethanol several timeswith a yield of 39 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With sodium hydroxide In water at 140℃; for 72h; Sealed tube; | Synthesis of Complex 2 A mixture containing Co(NO3)26H2O (29.1 mg,0.1 mmol), ZnBr2 (22.5 mg, 0.1 mmol), H3BTC (21.0 mg,0.1 mmol), titmb (36.0 mg, 0.1 mmol) and NaOH(12.0 mg, 0.3 mmol) in 15 ml deionized water was sealedin a 25 ml Teflon lined stainless steel container and heated at 140 C for 3 days. Pale purple cubic crystals of 2 werecollected by filtration and washed with water and ethanolseveral times with a yield of 68 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 72 h / Reflux 2: ammonium hexafluorophosphate / water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetonitrile / 72 h / Reflux 2: ammonium hexafluorophosphate / water 3: tetrabutyl-ammonium chloride / [D3]acetonitrile / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile for 72h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In [D3]acetonitrile at 20℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 20 - 180℃; | 2.1; 2.2; 3 The preparation of the complex constructed by the flexible triimidazole ligand specifically adopts the following steps: Step 1: Put 1,3,5-tris(imidazolylmethyl)-2,4,6-trimethylbenzene, phthalic acid, zinc acetate dihydrate in a molar ratio of 2:3:3 in water In a mixed solution with ethanol, wherein the volume ratio of water to ethanol is (3 to 4): 1, and the mixture is stirred at room temperature to obtain a mixed suspension, which is used;Step 2: Transfer the mixed suspension obtained in the first step to the reaction kettle.The volume of the mixed suspension accounts for 1/2 to 2/3 of the volume of the reactor.After reacting at 150 ° C to 180 ° C for 2 to 4 days, the temperature is lowered to room temperature at a temperature decreasing rate of (8 to 10) ° C / h to obtain colorless crystals.That is, the complex crystal constructed by the flexible triimidazole ligand in the present invention. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform for 15h; Reflux; | TINP: General procedure: 2 (0.18 g, 0.5 mmol) and 1 (0.45 g, 1.6 mmol) were dissolvedin CHCl3 (20 mL) and stirred at reflux for 15 h. During this time, a whiteprecipitate formed. The product was filtered off and washed with CHCl3 to give the desired tribromo anions product as a yellow powder. A solutionof the mixture of 3Br product (0.39 g, 0.35 mmol) and NaClO4(0.44 g, 1.3 mmol) was stirred at room temperature in CH3OH (30 mL)for 1 h. The yellow precipitated formed was filtered, washed withmethanol and diethyl ether, and dried in vacuo. Yield 0.32 g (73%). M.p.146-148 C; Anal calc. for C54H54Cl3N15O15: C 51.50, H 4.32, N 16.68%.Found: C 51.47, H 4.35, N 16.61%; 1H NMR (400 MHz, DMSO-d6) δ:10.94 (s, 3H), 9.01 (s, 3H), 8.47 (m, 6H), 8.34 (d, J 8, 3H), 7.85 (d, J 12, 3H), 7.70 (d, J 8, 3H), 7.50 (d, J 8, 3H), 5.65 (s, 6H), 5.64 (s,6H), 2.50 (s, 9H), 2.16 (s, 9H); 13C NMR (101 MHz, DMSO-d6) δ 166.2,165.9, 164.2, 164.0, 158.2, 142.1, 137.2, 132.1, 131.5, 129.5, 126.8,124.1, 122.2, 115.1, 53.8, 49.1, 23.6, 18.2 ppm; LCQ-Tof MS: 320.2190[M]3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform for 15h; Reflux; | TINP: 2 (0.18 g, 0.5 mmol) and 1 (0.45 g, 1.6 mmol) were dissolvedin CHCl3 (20 mL) and stirred at reflux for 15 h. During this time, a whiteprecipitate formed. The product was filtered off and washed with CHCl3 to give the desired tribromo anions product as a yellow powder. A solutionof the mixture of 3Br product (0.39 g, 0.35 mmol) and NaClO4(0.44 g, 1.3 mmol) was stirred at room temperature in CH3OH (30 mL)for 1 h. The yellow precipitated formed was filtered, washed withmethanol and diethyl ether, and dried in vacuo. Yield 0.32 g (73%). M.p.146-148 C; Anal calc. for C54H54Cl3N15O15: C 51.50, H 4.32, N 16.68%.Found: C 51.47, H 4.35, N 16.61%; 1H NMR (400 MHz, DMSO-d6) δ:10.94 (s, 3H), 9.01 (s, 3H), 8.47 (m, 6H), 8.34 (d, J 8, 3H), 7.85 (d, J 12, 3H), 7.70 (d, J 8, 3H), 7.50 (d, J 8, 3H), 5.65 (s, 6H), 5.64 (s,6H), 2.50 (s, 9H), 2.16 (s, 9H); 13C NMR (101 MHz, DMSO-d6) δ 166.2,165.9, 164.2, 164.0, 158.2, 142.1, 137.2, 132.1, 131.5, 129.5, 126.8,124.1, 122.2, 115.1, 53.8, 49.1, 23.6, 18.2 ppm; LCQ-Tof MS: 320.2190[M]3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In toluene; acetonitrile at 50℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | In water; N,N-dimethyl-formamide at 110℃; for 72h; | 2.1.3. Synthesis of [Co(nip)(titb)]·H2O}n (3) A mixture of CoCl2·6H2O (0.119 g, 0.5 mmol), H2nip (0.110 g, 0.5mmol), titb (0.180 g, 0.5 mmol), and 4 mL mixed solvent of H2O andDMF (v/v = 1:1) was added to a Teflon-lined stainless steel container(23 mL), and stirred for 20 min, then heated at 110 °C for three days.After cooled to room temperature at a rate of 5 °Ch -1, deep red blockcrystals formed. The obtained samples were finally filtered, washed withmother liquid and dried in air (yield: 45% based on H2nip). Elementalanalysis (%) calcd. for 3 (C29 H23CoN7O7): C, 54.38; H, 3.62; N, 15.31.Found: C, 54.97; H, 3.48; N, 14.75. IR (KBr, cm-1): 3320(m), 3109(w),2957(m), 1637(s), 1619(m), 1522(m), 1513(s), 1457(m), 1431(s), 1420(m), 1356(m), 1369(m), 1292(m), 1222(w), 810(w), 744(w), 659(w). |
[ 65039-11-4 ]
1-Benzyl-3-methyl-1H-imidazol-3-ium bromide
Similarity: 0.89