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[ CAS No. 525-64-4 ] {[proInfo.proName]}

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Chemical Structure| 525-64-4
Chemical Structure| 525-64-4
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Product Details of [ 525-64-4 ]

CAS No. :525-64-4 MDL No. :MFCD00001128
Formula : C13H12N2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 196.25 Pubchem ID :-
Synonyms :

Safety of [ 525-64-4 ]

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 [ 525-64-4 ]

* 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 [ 525-64-4 ]

[ 525-64-4 ] Synthesis Path-Downstream   1~11

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YieldReaction ConditionsOperation in experiment
76% With oxygen; caesium carbonate; In dimethyl sulfoxide; 5.1.1.30 2,7-Diamino-9H-fluoren-9-one (35) A mixture of 9H-fluorene-2,7-diamine (294 mg, 1.5 mmol) and Cs2CO3 (1.5 g, 4.5 mmol) in DMSO (7 mL) was stirred under an atmosphere of air. When TLC showed that no starting material remained, the solution was poured into water and a precipitate was formed. The product was filtered, washed with water, and air-dried. Without any purification, 35 (239 mg, 76%) was obtained as a solid. 1H NMR (DMSO-d6, δ = 2.5 ppm, 400 MHz): 7.10 (s, 1H), 7.08 (s, 1H), 6.70 (d, 2H), 6.57 (d, 1H), 6.57 (d, 1H) 5.30 (s, 4H). 13C NMR (DMSO-d6, δ = 39.52 ppm, 100 MHz): 194.9, 148.2, 134.6, 133.3, 119.9, 118.6, 109.7. HRMS: Anal. calcd. for [M+H]+ C13H10N2O: 211.0866; found 211.0867.
76% With caesium carbonate; In dimethyl sulfoxide; Preparative Example 12Preparation of 2,7-diamino-9H-fluorene-9-one 10206] The mixture of 9H-fluorene-2,7-diamine (294 mg,1.5 mmol) and Cs2CO3 (1.5 g, 4.5 mmol) were dissolved inDMSO (7 mE), followed by mixing under an atmosphere ofair. When the termination of the reaction was confirmed byTEC, water was added to the mixture to obtain a precipitate.The precipitate was filtered and washed with water and dried.Without any purification process, the target compound wasobtained as a solid (239 mg, yield: 7 6%).10207] ‘H NMR (DMSO-d5, &2.5 ppm, 400 MHz): 7.10(s, 1H), 7.08 (s, 1H), 6.70 (d, 2H), 6.57 (d, 1H), 6.57 (d, 1H)5.30 (s, 4H).10208] ‘3C NMR (DMSO-d5, ö39.52 ppm, 100 MHz):194.9, 148.2, 134.6, 133.3, 119.9, 118.6, 109.7.10209] EC/MS: Anal. Calcd. For [M+H] C,3H,0N20: 211.0866; found 211.0867.
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  • [ 17557-76-5 ]
  • soda lime [ No CAS ]
  • [ 525-64-4 ]
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  • [ 17557-76-5 ]
  • barium hydroxide [ No CAS ]
  • [ 525-64-4 ]
  • [ 15719-64-9 ]
  • [ 92-87-5 ]
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  • [ 17557-76-5 ]
  • quicklime [ No CAS ]
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  • [ 153-78-6 ]
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  • [ 295796-57-5 ]
  • polymer, MW = 1816 g mol-1, degree of polymerization DPn = 2, DPmax = 6; monomer(s): 9,9-dihexyl-9H-fluorene-2,7-dicarbaldehyde; 2,7-diaminofluorene; 2-aminofluorene [ No CAS ]
  • 7
  • [ 525-64-4 ]
  • [ 107819-90-9 ]
  • [ 853579-35-8 ]
YieldReaction ConditionsOperation in experiment
68% With triethylamine; mercury dichloride; In N,N-dimethyl-formamide; at 20℃; for 24h; To a solution of 2,7-diamino fluorene (3a) (0.49 g, 2.5 mmol) in anhydrous DMF (15 mL) was added 1,3-bis (tert-butoxycarbonyl)-2-methylthiopseudourea (1.56 g, 5.3 mmol), triethylamine (3.23 g, 32 mmol) and finally mercury (II) chloride (1.57 g, 5.7 mmol). The suspension was kept stirring at room temperature for 24 h. The reaction, diluted with CH2CI2 and Na2CO3 solution, was filtered through a pad of Celite. The organic layer was washed with water (3X) followed by brine and then dried over anhydrous Na2SO4. After evaporating the solvent to dryness the obtained residue was recrystallized from CH2CI2/MeOH giving a light yellow solid (1. 15 g, 68percent), mp >340 °C.'H-NMR (CDC13) : 8 1.52, 1.54 (2s, 36H), 3.91 (s, 2H), 7.47 (d, J = 8. 4 Hz, 2H), 7.64 (d, J = 8. 4 Hz, 2H), 7.90 (s, 2H), 10.43 (s, 2H), 11. 68 (s, 2H).'3C-NMR (CDC13) : 5163. 6,153. 5,153. 3,144. 2,138. 0, 135. 2, 120.9, 119.7, 118.9, 83. 6, 79.6, 37.2, 28.1, 28.1. Anal. Calcd. for C35H48N608 (680.79) : C percent 61.75, H percent 7. 11, N percent 12.34. Found: C percent 61.50, H percent 7.11, N percent 12.36.
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  • 2,7-bis((E)-3,3,4,4,5,5,6,6,6-nonafluorohex-1-en-1-yl)-9H-fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% 3,3,4,4,5,5,6,6,6-Nonafluorohex-1-ene (12.9mL, 76.0mmol) and Pd(OAc)2 (854mg, 3.8mmol) was added to a solution of 4b (30.0g, 76.0mmol) in MeOH (560mL) at 40°C. After 30min, the catalyst was removed by filtration through a pad of Celite and washed with ethyl acetate, and then the filtrate was concentrated. The crude residue was purified by silica gel column chromatography (hexane) to give 5a (20.7g, 83percent) as a yellow solid; mp 115?116°C; 1H NMR (270MHz, CDCl3) delta 3.97 (s, 2H), 6.18?6.33 (m, 2H), 7.21?7.28 (m, 2H), 7.52 (d, J=7.6Hz, 2H), 7.70 (s, 2H), 7.81 (d, J=7.8Hz, 2H); 13C NMR (67.8MHz, CDCl3) delta 36.6, 108.7?120.0 (8C), 124.0, 127.1, 132.8, 139.6, 139.8, 139.9, 142.8, 144.4; 19F NMR (466MHz, CDCl3) delta ?80.9 (6F), ?111.0 (4F), ?123.9 (4F), ?122.5 (4F); IR (neat) 2961, 2930, 1651, 1472, 1422, 1352, 1229, 1207, 1128, 1098, 1030, 973, 811, 717, 690cm?1; HRMS [FAB+] m/z calcd for C25H13F18 655.0732 found 655.0718
  • 10
  • [ 15761-39-4 ]
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  • (2S,2'S)-di-tert-butyl 2,2'-(((9H-fluorene-2,7-diyl)bis(azanediyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 2h; 31 5.1.1.31. (2S,2'S)-Di-tert-butyl 2,2'-(((9H-fluorene-2,7-diyl)bis(azanediyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate) (36) 5.1.1.31 (2S,2'S)-Di-tert-butyl 2,2'-(((9H-fluorene-2,7-diyl)bis(azanediyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate) (36) A mixture of N-Boc-l-proline (323 mg, 1.5 mmol), EDCI (312 mg, 1.63 mmol), and 2,7-diaminofluorene (123 mg, 0.63 mmol) in CH2Cl2 (2 mL) was stirred at ambient temperature for 2 h. The resulting residue was partitioned between CH2Cl2 and H2O. The organic layer was washed with 1.0 N aq HCl solution and brine, dried over MgSO4, filtered, and concentrated in vacuo. Without any purification, 36 was obtained as a solid (359 mg, 97%). 1H NMR (DMSO-d6, δ = 2.5 ppm, 400 MHz): 10.0 (d, 2H), 7.69 (d, 2H), 7.72 (d, 2H), 7.57-7.51 (m, 2H), 4.31-4.21 (m, 2H), 3.88 (s, 2H), 3.45-3.37 (m, 4H), 2.23 (m, 2H), 1.94-1.80 (m, 6H), 1.41 (app br s, 9H), 1.29 (app br s, 9H). 13C NMR (DMSO-d6, δ = 39.52 ppm, 100 MHz): 171.4, 153.2, 143.5, 137.6, 136.3, 119.5, 118.0, 116.1, 78.6, 78.5, 60.4, 46.6, 31.1, 28.2, 28.0, 24.0, 23.4. HRMS: Anal. calcd. for [M+H]+ C33H42N4O6: 591.3177; found 591.3168.
97% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; 4 Example 4 Preparation of dimethyl((1R,1'R)-((2S,2'S)-2,2'-(((9H-fluorene-2,7-diyl)bis(azandiyl))bis(carbonyl))bis(pyrrolidine-2,1-diyl))bis(2-oxo-1-phenylethane-2,1-diyl))dicarbamate N-Boc-L-proline (323 mg, 1.5 mmol), EDC (312 mg, 1.63 mmol), and 2,7-diaminofluorene (123 mg, 0.63 mmol) were mixed in CH2Cl2 (2 mL), followed by stirring at room temperature for 2 hours. Then, the compound obtained above was fractionated with CH2Cl2 and H2O. The organic layer was washed with 1 N HCl aqueous solution and brine, dried over MgSO4, filtered, and concentrated under reduced pressure. Without any additional purification process, (2S,2'S)-di-tert-butyl 2,2'-(((9H-fluorene-2,7-diyl)bis(azandiyl))bis(carbonyl))bis(pyrrolidine-1-carboxylate), the target compound, was obtained as a solid (359 mg, yield: 97%).
80% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 0.75h; Cooling with ice; Inert atmosphere; Schlenk technique;
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  • C138H108N12 [ No CAS ]
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