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[ CAS No. 13629-22-6 ] {[proInfo.proName]}

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Chemical Structure| 13629-22-6
Chemical Structure| 13629-22-6
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Product Details of [ 13629-22-6 ]

CAS No. :13629-22-6 MDL No. :MFCD00016357
Formula : C13H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 194.23 Pubchem ID :-
Synonyms :

Safety of [ 13629-22-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13629-22-6 ]

* 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 [ 13629-22-6 ]

[ 13629-22-6 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 486-25-9 ]
  • [ 13629-22-6 ]
YieldReaction ConditionsOperation in experiment
99% With hydrazine hydrate In ethanol for 15h; Reflux;
95% With hydrazine hydrate for 4h; Reflux; 1 Example 1: Synthesis of fluorenyl salicylaldide hydrazine (FAS) 10 g of fluorenone was refluxed with 20 ml of hydrazine hydrate (85%) at 100 ml for 4 h, After cooling a large number of needle-like solid precipitation, After filtration, the crystals were recrystallized twice with ethanol, Get light yellow needle mounted crystal, Purity 99% Yield 95%; Take 2g hydrazine hydrate crystals and 2ml salicylaldehyde in 20ml ethanol refluxed for 4h, After cooling to get light yellow needle mounted crystal ,After filtration, Washed with 75% ethanol solution, Get FAS structure,Yield 99%.
93% With hydrazine In water; butan-1-ol for 4h; Reflux;
93% With hydrazine In ethanol at 80℃; for 12h; 5 (9H-fluoren-9-ylidene) hydrazine (Ml) 9H-fluoren-9-one (5.0 g, 27.75 mmol) was dissolved in absolute ethanol (70 ml)followed by addition of hydrazine (20 mL), and the mixture was refluxed for 12 h. Precipitates were filtrated under vacuum and washed with absolute ethanol three times, then dried under vacuum to give a yellow needle crystal (5.0 g, 93% yield).
91% With hydrazine hydrate; acetic acid In ethanol for 12h; Reflux; Inert atmosphere;
90% With hydrazine In ethanol; water for 10h; Reflux; 2.1.1 Synthesis of (9H-fluoren-9-ylidene)hydrazine (FL-1) A solution of 9-fluorenone (0.50 g, 2.78 mmol) was dissolved in 10 mL of ethanol, and 98 % aqueous N2H4 (0.8 mL) was added into the resulting solution. The reaction mixture was heated under reflux for 10 h. The reaction mixture was then cooled to room temperature (RT), and the precipitate was filtered and dried to give a yellow solid (0.49 g, 90 %). 1H NMR (Supporting information, Fig. S1) (300 MHz, DMSO-d6): δ/ppm 8.18 (d, J =6.9 Hz, 1 H), 7.98 (s, 2 H), 7.88 (d, J =1.2 Hz, 1 H), 7.86-7.76 (m, 1 H), 7.68-7.65 (m, 1 H), 7.45-7.37 (m, 2 H), 7.35-7.28 (m, 2 H); 13C NMR (Supporting information, Fig. S2) (75 MHz, DMSO-d6): δ/ppm 139.7, 139.6, 138.4, 137.3, 129.8, 129.1, 128.1, 128.0, 127.8, 125.5, 120.7, 120.2, 120.1.
88% With hydrazine hydrate In ethanol for 6h; Heating;
87% With hydrazine hydrate In ethanol for 16h; Heating;
85% With hydrazine hydrate In ethanol for 6h; Inert atmosphere; Reflux; General procedure for synthesis of 9-fluorenone hydrazone1 Fluorenone (5.40 g, 30 mmol) was dissolved in ethanol (100 mL), then hydrazine hydrate (12.0 ml, 240 mmol) was added and refluxed for 6 h. The reaction was cooled to room temperature, a large number of yellowish acicular crystals were precipitated, filtered and successively washed with ethanol. Yellowish crystals (4.95 g, 85%) were obtained by drying the product.
83% With hydrazine hydrate In ethanol for 2h; Inert atmosphere; Reflux;
81% With hydrazine hydrate In ethanol for 6h; Reflux; (9H-Fluoren-9-ylidene)hydrazine (6a). To an ethanol (10mL) solution of fluoren-9-one (360mg, 2.0mmol, 1.0eq) was added hydrazine monohydrate (0.29mL, 6.0 mmol, 3.0eq) dropwise at room temperature. The reaction mixture was refluxed for 6 h and then concentrated in vacuo. The residue was diluted with ethyl acetate (100mL) and washed with water (2×30mL) and brine (40mL). The organic layer was dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography over silica gel (hexane/ethyl acetate, 10:1, v/v) to afford the desired product 6a (315 mg, 81%) as yellow solid: Rf=0.15 (hexane/ethyl acetate, 10:1, v/v); mp 152-154°C; 1H NMR (CDCl3, 500 MHz) δ 7.91 (d, J=7.5 Hz, 1H), 7.77 (d, J=7.5 Hz, 1H), 7.73 (d, J=7.0 Hz, 1H), 7.65 (d, J=7.5 Hz, 1H), 7.44 (t, J=7.5 Hz, 1H), 7.37-7.29 (d, 3H), 6.41 (s, 2H); 13C NMR (CDCl3, 125 MHz) δ 145.6, 141.3, 138.6, 137.7, 130.2, 129.7, 128.5, 127.9, 127.7, 125.5, 120.8, 120.5, 119.5 ppm; DART-HRMS found 195.09088 [M+H]+, calcd for C13H11N2 195.09222.
81% With hydrazine hydrate In ethanol at 20℃; for 6h; Reflux; (9H-Fluoren-9-ylidene)hydrazine (6a). To an ethanol (10 mL) solution of fluoren-9-one (360 mg, 2.0 mmol, 1.0 eq) was added hydrazine monohydrate (0.29 mL, 6.0 mmol, 3.0 eq) dropwise at room temperature. The reaction mixture was refluxed for 6 h and then concentrated in vacuo. The residue was diluted with ethyl acetate (100 mL) and washed with water (2 X 30 mL) and brine (40 mL). The organic layer was dried with MgS04, filtered and concentrated in vacuo. The residue was purified by flash column (0275) chromatography over silica gel (hexane/ethyl acetate, 10: 1, v/v) to afford the desired product 6a (315 mg, 81%) as yellow solid: Rf = 0.15 (hexane/ethyl acetate, 10: 1, v/v); mp (0276) 152-154 °C; 1H NMR (CDCh, 500 MHz) δ 7.91 (d, J= 7.5 Hz, 1H), 7.77 (d, J= 7.5 Hz, 1H), 7.73 (d, J= 7.0 Hz, 1H), 7.65 (d, J= 7.5 Hz, 1H), 7.44 (t, J= 7.5 Hz, 1H), 7.37-7.29 (d, 3H), 6.41 (s, 2H); 13C NMR (CDCh, 125 MHz) δ 145.6, 141.3, 138.6, 137.7, 130.2, 129.7, 128.5, 127.9, 127.7, 125.5, 120.8, 120.5, 119.5 ppm; DART-HRMS found 195.09088 [M+H]+, calcd for C13H11N2 195.09222.
76% With hydrazine hydrate; acetic acid In ethanol for 16h; Reflux;
74% With hydrogenchloride; hydrazine hydrate In isopropyl alcohol 1 9-Fluorenone Hydrazone 9-Fluorenone Hydrazone 9-Fluorenone (200 g, 1.1 mol, from Aldrich, Milwaukee, Wis.) and hydrazine monohydrate (160 ml, 3.3 mol, from Aldrich, Milwaukee, Wis.) were dissolved in 1000 ml of 2-propanol in a 2000 ml 2-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. Concentrated hydrochloric acid (4 ml) was then added, and the mixture was refluxed for one hour. The mixture was cooled slowly to room temperature, and the crude solid product was harvested by filtration. The solid was washed with isopropanol and then recrystallized from dioxane to obtain 150 g (74% yield) of 9-fluorenone hydrazone.
63% With hydrazine hydrate In ethanol for 18h; Reflux;
With ethanol; hydrazine hydrate
Multi-step reaction with 2 steps 1: ethanol / Heating 2: N2H4 / ethanol / Heating
With hydrazine hydrate; acetic acid In tetrahydrofuran at 60℃; for 2h;
With hydrazine hydrate; acetic acid In ethanol for 20h; Reflux;
With toluene-4-sulfonic acid; hydrazine hydrate In water at 75℃;
With hydrazine hydrate In ethanol
0.8 g With hydrazine hydrate In tetrahydrofuran at 500℃; for 6h; 2 20 mL of hydrazine monohydrate and 20 mL of ethanol were put into a reactor. 10 mL of a tetrahydrofuran solution of 1.0 g of a compound represented by the formula (I-2-1) was added thereto and heated with stirring at 500° C. for 6 hours. The solvent was evaporated away, and the residue was redissolved in dichloromethane, and washed with salt solution. This was Purified through column chromatography (silica gel, dichloromethane/methanol) and recrystallization (dichloromethane/hexane) to give 0.8 g of a compound represented by the formula (I-2-2).
With hydrazine hydrate; acetic acid In ethanol for 24h; Reflux;
With hydrazine hydrate; acetic acid In methanol for 6h; Reflux;

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[2]Current Patent Assignee: HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN106146342, 2016, A Location in patent: Paragraph 0065; 0066; 0067
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[4]Current Patent Assignee: HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY - WO2016/206615, 2016, A1 Location in patent: Paragraph 158; 159; 165; 166
[5]Gazis, Theodore A.; Dasgupta, Ayan; Hill, Michael S.; Rawson, Jeremy M.; Wirth, Thomas; Melen, Rebecca L. [Dalton Transactions, 2019, vol. 48, # 33, p. 12391 - 12395]
[6]Chiou, Yi-Ru; Yan, Hongbin; Wan, Chin‐Feng; Yen Huang, Chi; Wu, An-Tai [Journal of Photochemistry and Photobiology A: Chemistry, 2020, vol. 390]
[7]Minabe, Masahiro; Takabayashi, Yutaka; Setta, Yuji; Nakamura, Hidenao; Kimura, Takao; Tsubota, Motohiro [Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 12, p. 3633 - 3638]
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  • 2
  • [ 4519-46-4 ]
  • [ 13629-22-6 ]
  • [ 41825-93-8 ]
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  • [ 20615-64-9 ]
  • [ 13629-22-6 ]
  • [ 102214-05-1 ]
  • 4
  • [ 113282-74-9 ]
  • [ 13629-22-6 ]
  • [ 1283714-81-7 ]
  • [ 1283714-82-8 ]
YieldReaction ConditionsOperation in experiment
In ethanol at 20 - 25℃; for 24h;
  • 5
  • [ 726-42-1 ]
  • [ 13629-22-6 ]
  • [ 1445265-14-4 ]
YieldReaction ConditionsOperation in experiment
98% With [Ti(pentamethylcyclopentadienyl)(N(xylyl)C4H6N)(tert-butylimido)(tert-butylamine)] In 1,4-dioxane at 80℃; for 24h; Inert atmosphere; Schlenk technique;
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  • [ 1892-57-5 ]
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  • [ 1445265-19-9 ]
  • 7
  • [ 1207448-58-5 ]
  • [ 13629-22-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
80% In ethanol at 60℃; for 12h; 5 (E)-2-(((9H-fluoren-9-ylidene)hydrazono)methyl)-5-((6-bromohexyl)oxy)phenol 4-((6-bromohexyl)oxy)-2-hydroxybenzaldehyde (M2, 2.0 g, 6.64 mmol) was dissolved in absolute ethanol (30m1), followed by addition of (9H-fluoren-9-ylidene)hydrazine (Ml, 1.37 g, 7.1 mmol), and the mixture was reacted at 60°C for 12 hrs. Precipitates were filtrated under vacuum and washed with absolute ethanol three times, then dried under vacuum.The residue was further separated by column chromatography (silica, petroleum ether/dichloromethane=1/3) to give a yellow powder solid (2.54 g, 80 % yield). ‘H NIVIR (400 MHz, CDC13) (5 12.08 (s, 1H), 8.71 (s, 1H), 8.27 (d, J = 7.6 Hz, 1H), 7.90 (d, J = 7.5 Hz, 1H),7.61 (dd, J = 17.2, 7.4 Hz, 2H), 7.50-7.38 (m, 2H), 7.38-7.24 (m, 4H), 6.57 (m, 3H), 4.03 (t, J =6.4 Hz, 2H), 3.73 (t, J = 4.6 Hz, 2H), 2.46 (m, 2H), 2.35 (m, 2H), 1.94-1.66 (m, 2H), 1.53-1.39 (m, 4H).
  • 8
  • [ 13629-22-6 ]
  • [ 53342-27-1 ]
  • 2-(1-((9H-fluoren-9-ylidene)hydrazono)ethyl)pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With p-toluenesulfonic acid monohydrate; In toluene; at 23℃; for 16h;Inert atmosphere; General procedure: to a solution of 9-fluorenone hydrazone (1.0equiv) in anhydrous toluene (0.25 M) was added the appropriate aldehyde or ketone (1.0to 1.2 equiv), followed by catalytic p-toluenesulfonic acid monohydrate (0.025 equiv).The mixture was stirred at 23 C for 16 h. After this time, the reaction mixture wasconcentrated, and the crude material was purified by column chromatography
  • 9
  • [ 18282-51-4 ]
  • [ 13629-22-6 ]
  • [ 1836-87-9 ]
  • [ 1572-46-9 ]
YieldReaction ConditionsOperation in experiment
1: 25% 2: 40% With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); 1,3-bis-(diphenylphosphino)propane; potassium <i>tert</i>-butylate In 1,4-dioxane at 110℃; for 9h; Inert atmosphere; General procedure for Ni-catalyzed reaction of 9-fluorenone hydrazone and benzylic alcohols General procedure: An oven-dried 25-mL flask was charged with t-BuOK (0.75 mmol), Ni(PPh3)2(1-naphthyl)Cl (0.025 mmol) and DPPP (0.025 mmol). Then the 9-fluorenone hydrazone (0.5 mmol) and the benzyl alcohol (1.5 mmol) (if solid) were added. The flask was evacuated and backfilled with nitrogen, with the operation being repeated twice. Dried 1,4-dioxane (4 mL) and the benzyl alcohol (1.5 mmol) (if liquid) were added via syringe at this time. The reaction mixture was performed on WATTECS WP-TEC-1020 parallel reactor of 110 °C for 9 h and then allowed to cool to room temperature; it was then filtered through a silica-gel pad that was washed with ethyl acetate. The combined organic phases were evaporated under reduced pressure and the residue purified by silica-gel column chromatography to give the desired products.
  • 10
  • [ 1592-38-7 ]
  • [ 13629-22-6 ]
  • 9-(naphthalen-2-ylmethyl)-9H-fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); 1,3-bis-(diphenylphosphino)propane; potassium <i>tert</i>-butylate In 1,4-dioxane at 110℃; for 9h; Inert atmosphere; General procedure for Ni-catalyzed reaction of 9-fluorenone hydrazone and benzylic alcohols General procedure: An oven-dried 25-mL flask was charged with t-BuOK (0.75 mmol), Ni(PPh3)2(1-naphthyl)Cl (0.025 mmol) and DPPP (0.025 mmol). Then the 9-fluorenone hydrazone (0.5 mmol) and the benzyl alcohol (1.5 mmol) (if solid) were added. The flask was evacuated and backfilled with nitrogen, with the operation being repeated twice. Dried 1,4-dioxane (4 mL) and the benzyl alcohol (1.5 mmol) (if liquid) were added via syringe at this time. The reaction mixture was performed on WATTECS WP-TEC-1020 parallel reactor of 110 °C for 9 h and then allowed to cool to room temperature; it was then filtered through a silica-gel pad that was washed with ethyl acetate. The combined organic phases were evaporated under reduced pressure and the residue purified by silica-gel column chromatography to give the desired products.
  • 11
  • [ 4780-79-4 ]
  • [ 13629-22-6 ]
  • 9-(naphthalen-1-ylmethyl)-9H-fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); 1,3-bis-(diphenylphosphino)propane; potassium <i>tert</i>-butylate In 1,4-dioxane at 110℃; for 9h; Inert atmosphere; General procedure for Ni-catalyzed reaction of 9-fluorenone hydrazone and benzylic alcohols General procedure: An oven-dried 25-mL flask was charged with t-BuOK (0.75 mmol), Ni(PPh3)2(1-naphthyl)Cl (0.025 mmol) and DPPP (0.025 mmol). Then the 9-fluorenone hydrazone (0.5 mmol) and the benzyl alcohol (1.5 mmol) (if solid) were added. The flask was evacuated and backfilled with nitrogen, with the operation being repeated twice. Dried 1,4-dioxane (4 mL) and the benzyl alcohol (1.5 mmol) (if liquid) were added via syringe at this time. The reaction mixture was performed on WATTECS WP-TEC-1020 parallel reactor of 110 °C for 9 h and then allowed to cool to room temperature; it was then filtered through a silica-gel pad that was washed with ethyl acetate. The combined organic phases were evaporated under reduced pressure and the residue purified by silica-gel column chromatography to give the desired products.
  • 12
  • [ 636-72-6 ]
  • [ 13629-22-6 ]
  • 2-((9H-fluoren-9-yl)methyl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); 1,3-bis-(diphenylphosphino)propane; potassium <i>tert</i>-butylate In 1,4-dioxane at 110℃; for 9h; Inert atmosphere; General procedure for Ni-catalyzed reaction of 9-fluorenone hydrazone and benzylic alcohols General procedure: An oven-dried 25-mL flask was charged with t-BuOK (0.75 mmol), Ni(PPh3)2(1-naphthyl)Cl (0.025 mmol) and DPPP (0.025 mmol). Then the 9-fluorenone hydrazone (0.5 mmol) and the benzyl alcohol (1.5 mmol) (if solid) were added. The flask was evacuated and backfilled with nitrogen, with the operation being repeated twice. Dried 1,4-dioxane (4 mL) and the benzyl alcohol (1.5 mmol) (if liquid) were added via syringe at this time. The reaction mixture was performed on WATTECS WP-TEC-1020 parallel reactor of 110 °C for 9 h and then allowed to cool to room temperature; it was then filtered through a silica-gel pad that was washed with ethyl acetate. The combined organic phases were evaporated under reduced pressure and the residue purified by silica-gel column chromatography to give the desired products.
  • 13
  • [ 12126-50-0 ]
  • [ 168704-96-9 ]
  • [ 13629-22-6 ]
  • [Cp*2Fe][C12H8CNNH(Al(C6F5)3)] [ No CAS ]
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