The important role of Ferrocene

With the complex challenges of chemical substances, we look forward to future research findings about Ferrocene

Name is Ferrocene, as a common heterocyclic compound, it belongs to iron-catalyst compound, and cas is 102-54-5, its synthesis route is as follows.,102-54-5

General procedure: A solution 3-5mmol of ferrocene in dichloromethane (DCM) or dichloroethane (DCE) (3-5mL) was prepared. A previously prepared solution of 1equivalent of acyl chloride and 1equivalent of aluminum chloride in DCM or DCE (3-5mL) was transferred to the ferrocene solution, while stirring and with positive nitrogen pressure. The mix of the two liquids generated an intense purple or blue mixture. Reaction was stopped after 30-60min of stirring at room temperature. An equal quantity of water was added to the reaction mixture. The organic phase was separated and the aqueous phase was extracted with methyl t-butyl ether (MTBE), and the combined organic phase was dried over anhydrous sodium sulfate. The solvent was removed and the crude product (red to orange solid) was purified by column chromatography column on silica gel (230-400mesh) with a gradient of cyclohexane-benzene as eluent.

With the complex challenges of chemical substances, we look forward to future research findings about Ferrocene

Reference£º
Article; Garcia-Barrantes, Pedro M.; Lamoureux, Guy V.; Perez, Alice L.; Garcia-Sanchez, Rory N.; Martinez, Antonio R.; San Feliciano, Arturo; European Journal of Medicinal Chemistry; vol. 70; (2013); p. 548 – 557;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

The important role of 102-54-5

With the complex challenges of chemical substances, we look forward to future research findings about Ferrocene

Name is Ferrocene, as a common heterocyclic compound, it belongs to iron-catalyst compound, and cas is 102-54-5, its synthesis route is as follows.,102-54-5

1. Mix acetic anhydride and phosphoric acid and stir at room temperature for 15 minutes;2, adding ferrocene solids, heated to 40 C for 1 hour;3. Raise the temperature to 50 C and react until the ferrocene reaction is complete;4. The reaction solution is rapidly poured into crushed ice, and the pH is adjusted to 6 to 7 with sodium bicarbonate solids, and the crude acetylferrocene is obtained by filtration.5. Pure acetyl ferrocene is obtained by recrystallization from petroleum ether.In this example, acetic anhydride: phosphoric acid: ferrocene solids = 3:1:0.5.By elemental analysis tests, the product was confirmed to be acetylferrocene.The yield is above 95%.The reaction conditions for the synthesis of acetylferrocene are mild, the temperature is easy to control, and the preparation yield is high.

With the complex challenges of chemical substances, we look forward to future research findings about Ferrocene

Reference£º
Patent; Suzhou Tianyun Metal Materials Co., Ltd.; Wang Ming; (5 pag.)CN107488199; (2017); A;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

The important role of Ferrocene

102-54-5 is used more and more widely, we look forward to future research findings about Ferrocene

As a common heterocyclic compound, it belongs to iron-catalyst compound, name is Ferrocene, and cas is 102-54-5, its synthesis route is as follows.,102-54-5

Acetylferrocene was synthesizedaccording to previously reported procedures [49]. Briefly, 85% phosphoric acid (4?mL) was slowly added to a stirred solution of ferrocene (4.0?g, 21.5?mmol) and acetic anhydride (13.3?mL, 140.0?mmol). The mixture was heated in a water bath maintained at 50?C for 10?min and then cooled in ice. Water (25?mL) was added to the mixture, that was then neutralized with NaHCO3 until the end of CO2 formation. CH2Cl2 (50?mL) was added and the orange organic layer was separated and retained in the dark, whereas the brown-coloured aqueous layer washed with a further 20?mL of CH2Cl2. The combined organic fractions were washed twice with water and then dried with anhydrous magnesium sulfate. Crude acetyl ferrocene, obtained removing the solvent under reduced pressure, was purified by silica gel column chromatography using a 95/5 mixture of petroleum ether/ethyl acetate as starting eluent to first separate the unreacted ferrocene. Once the ferrocene was eluted, the eluent was replaced by 100% ethyl acetate to collect acetyl ferrocene, that was then obtained by removing the solvent on a rotary evaporator.

102-54-5 is used more and more widely, we look forward to future research findings about Ferrocene

Reference£º
Article; Paucar, Rocio; Martin-Escolano, Ruben; Moreno-Viguri, Elsa; Cirauqui, Nuria; Rodrigues, Carlos Rangel; Marin, Clotilde; Sanchez-Moreno, Manuel; Perez-Silanes, Silvia; Ravera, Mauro; Gabano, Elisabetta; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 569 – 582;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

The important role of 102-54-5

With the complex challenges of chemical substances, we look forward to future research findings about Ferrocene

Name is Ferrocene, as a common heterocyclic compound, it belongs to iron-catalyst compound, and cas is 102-54-5, its synthesis route is as follows.,102-54-5

A 250 mL round bottom reaction flask was charged sequentially with 1.46 g of aluminum trichloride (11 mmol) and 20 mL of dichloroethane,Under ice-water cooling, 0.8 mL of acetyl chloride (11 mmol)Continue stirring until almost dissolved aluminum trichloride.In another 250 mL round bottom reaction flask,A solution of 1.86 g (ie 10 mmol) of ferrocene in dichloroethane was added,Under ice-cooling, the acetyl chloride-aluminum trichloride complex solution prepared above was dropped,Stirring to complete the reaction at room temperature (monitored by thin layer chromatography) takes about 2 hours.The reaction was poured into ice water,Separate the organic phase,Followed by water,5% sodium carbonate solution and water,Drying over anhydrous sodium sulfate.The solvent was removed under reduced pressure,A red oil was obtained,Recrystallization to give orange crystals of acetyl ferrocene,Yield 80%.

With the complex challenges of chemical substances, we look forward to future research findings about Ferrocene

Reference£º
Patent; Inner Mongolia University; Zhang Hao; Ling Li; Hu Jianfeng; Huo Yanhong; (11 pag.)CN107226829; (2017); A;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

Some tips on 102-54-5

With the complex challenges of chemical substances, we look forward to future research findings about Ferrocene

It is a common heterocyclic compound, the iron-catalyst compound, Ferrocene, cas is 102-54-5 its synthesis route is as follows.,102-54-5

Ferrocenecarboxaldehyde was prepared from ferrocene according to the literature.10 Phosphorus oxychloride (50mL, 536mmol) was added dropwise to the dimethylformamide (39.0g, 536mmol) at 0C and the resulting mixture was stirred for 30min at this temperature under a nitrogen atmosphere. Next ferrocene (50.0g, 268mmol) in dry chloroform (250mL) was added dropwise to the mixture for 30min at 0C. After completion of the addition, the reaction mixture was kept stirring for 28h with heating at 55-60C on an oil bath, taking care that the temperature did not exceed 60C. The reaction mixture was then cooled to room temperature and neutralized carefully with an aqueous saturated Na2CO3 solution and then extracted repeatedly with the dichloromethane. The combined organic layer was dried over anhydrous Na2SO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography using hexane/ ethyl acetate mixture (95:05) as eluent to give ferrocenecarboxaldehyde 1 in 55% yield (31.7g) as a reddish brown solid. (mp: 122C, lit.10 123C); IR (KBr, cm-1): 3093, 2837, 2760, 1683, 1447; 1H NMR (400MHz, CDCl3): deltaH 9.95 (s, 1H); 4.80-4.60 (m, 4H), 4.27 (s, 5H); 13C NMR (100MHz, CDCl3): deltaC 193.63, 79.49, 73.33, 69.78; HRMS-ESI (m/z): [M+H]+ Found 215.0157 and calculated 215.0159 for C11H11FeO.

With the complex challenges of chemical substances, we look forward to future research findings about Ferrocene

Reference£º
Article; Achari, Kamsali Murali Mohan; Ramanathan, Chinnasamy Ramaraj; Tetrahedron Asymmetry; vol. 28; 6; (2017); p. 830 – 836;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

Brief introduction of 102-54-5

The synthetic route of 102-54-5 has been constantly updated, and we look forward to future research findings.

102-54-5, Ferrocene is a iron-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,102-54-5

Under a nitrogen atmosphere, ferrocene (10 g, 53.8 mmol) was dissolved in anhydrous n-hexane (50 ml), followed by adding and mixing with tetramethylethylenediamine (TMEDA, 18.1 ml, 84.5 mmol) A solution of n-butyllithium (n-BuLi) in n-hexane (2.5 M, 48.0 ml) was added slowly dropwise at 0 C., followed by stirring at 25 C. After stirring for 12 hours and removing the solvent, a light orange yellow complex was formed. The complex was added to anhydrous ethyl ether (200 ml), followed by stirring to disperse the complex in anhydrous ethyl ether and lowering the temperature of the dispersion to -78 C. A solution of iodine (19.0 g) in ethyl ether (350 ml) was added to the dispersion slowly dropwise, and the temperature was raised to 25 C. After stirring for a further hour, the reaction was poured into an aqueous ferric chloride (FeCl3) solution (5 wt %, 100 ml), followed by extraction with ethyl ether (200 ml). An organic layer thus obtained was washed ten times with an aqueous ferric chloride (FeCl3) solution (5 wt %, 100 ml) and then was washed with water until the aqueous layer was clear. Thereafter, water was removed using anhydrous MgSO4 and solvent was also removed to obtain a mixture in the form of a blackish brown liquid of compound a and compound b as shown in scheme I in a molar ratio of 1:1. (0037) The obtained mixture (2.5 g, 6.67 mmol), cuprous iodide (CuI, 128 mg, 0.67 mmol), ferric chloride (FeCl3, 107 mg, 0.67 mmol), sodium hydroxide (NaOH, 540 mg, 13.3 mmol), aqueous ammonia (15 M, 30 ml), and ethanol (EtOH, 30 ml) were placed in a high pressure reaction tube of 150 ml. A reaction was conducted at 90 C. for 12 hours. After the temperature of the content in the reaction dropped to 25 C., ethyl ether (200 ml) was added and the content in the reaction tube was washed three times with an aqueous sodium hydroxide solution (1.0 M, 150 ml). Then, water was removed using anhydrous MgSO4 and solvent was also removed to obtain an orange brown crude product, which was purified by column chromatography (eluent: ethyl acetate/n-hexane=1/2 (v/v)) to obtain aminoferrocene compound c shown in Scheme I in the form of a yellowish brown solid (yield: 48%). (0038) 1H NMR (400 MHz, CDCl3) of aminoferrocene compound c: delta 4.08 (s, 5H), 3.97 (t, J=1.6, 2H), 3.82 (t, J=1.6, 2H), 2.58 (br, 2H).

The synthetic route of 102-54-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NATIONAL TSING HUA UNIVERSITY; Cheng, Chien-Hong; Lai, Cheng-Chang; Chang, Yu-Wei; Liao, Chuang-Yi; Huang, Min-Jie; (16 pag.)US9356244; (2016); B1;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

The important role of Ferrocene

102-54-5 is used more and more widely, we look forward to future research findings about Ferrocene

As a common heterocyclic compound, it belongs to iron-catalyst compound, name is Ferrocene, and cas is 102-54-5, its synthesis route is as follows.,102-54-5

The mixture of ferrocene (2.79 g, 15 mmol), DMF (2.19 g, 30 mmol) and chloroform (11 mL) was stirred at 0 C under N2 atmosphere. Phosphorus oxychloroide (4.59 g, 30 mmol) was added slowly over a period of 30 min at 0 C and stirred at the temperature range of 55-60 C for 24 h until the reaction was completed. The mixture was poured into ice-water (100 mL) and neutralized with 5% aqueous Na2CO3 accompanying the precipitate formation. The precipitate was filtered off and the filtrate was extracted with 100 mL of toluene. Then the organic phase was washed three times with water, dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure to give a crude product. The crude product was purified by column chromatography on silica gel to give compound 8a as a crimson solid (75.7%).

102-54-5 is used more and more widely, we look forward to future research findings about Ferrocene

Reference£º
Article; Chen, Peiqi; Liu, Chunjuan; Hu, Jianfeng; Zhang, Hao; Sun, Ranfeng; Journal of Organometallic Chemistry; vol. 854; (2018); p. 113 – 121;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

Analyzing the synthesis route of 102-54-5

The synthetic route of 102-54-5 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.102-54-5,Ferrocene,as a common compound, the synthetic route is as follows.,102-54-5

The alcohol 1b was synthesized by acylation offerrocene (Aldrich) with acetic anhydride in presence of BF3Et2O21followed by reduction of the resulting acetylferrocene withNaBH4.22

The synthetic route of 102-54-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Trofimov, Boris A.; Oparina, Ludmila A.; Tarasova, Olga A.; Artem’ev, Alexander V.; Kobychev, Vladimir B.; Gatilov, Yuriy V.; Albanov, Alexander I.; Gusarova, Nina K.; Tetrahedron; vol. 70; 35; (2014); p. 5954 – 5960;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

New learning discoveries about 102-54-5

As the paragraph descriping shows that 102-54-5 is playing an increasingly important role.

102-54-5, Ferrocene is a iron-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

DMF (8 mL) and POCl3 (5.6 mL, 60 mmol) were added to a round-bottom two-necked balloon adapted to a reflux condenser, containing ferrocene (2.79 g, 15 mmol) dissolved in chloroform (30 mL) under argon atmosphere and stirred at 0 C during 1.5 h. After addition was complete, the system was heated under reflux for 15 h. After completion, the reaction mixture was cooled to room temperature, poured on a beaker containing 100 mL ice-water mixture, neutralized/basified with aqueous 10% NaOH to pH 8-9 and extracted with ethyl acetate (3 * 50 mL). The organic layer was dried over MgSO4 and filtered. Solvent was then removed under low pressure (rotary evaporator) and 20 mL ethyl acetate was added to the crude product. The solvent was removed again under low pressure and the product was dried under reduced pressure, furnishing 2 as a dark red/brown solid, which was used without purification. Yield: 2.247 g, 70%. 1H NMR (CDCl3, 200 MHz): delta = 9.94 (s, 1 H); 4.78 (br, 2 H); 4.60 (br, 2 H); 4.27 (s, 5 H)., 102-54-5

As the paragraph descriping shows that 102-54-5 is playing an increasingly important role.

Reference£º
Article; Mayer, Joao C.P.; Sauer, Andre C.; Iglesias, Bernardo A.; Acunha, Thiago V.; Back, Davi F.; Rodrigues, Oscar E.D.; Dornelles, Luciano; Journal of Organometallic Chemistry; vol. 841; (2017); p. 1 – 11;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

Share a compound : 102-54-5

With the rapid development of chemical substances, we look forward to future research findings about Ferrocene

Ferrocene, cas is 102-54-5, it is a common heterocyclic compound, the iron-catalyst compound, its synthesis route is as follows.

102-54-5, General procedure: A solution of acid chloride (63mmol) in 30ml dry dichloromethane was added to a suspension of anhydrous aluminum chloride (8.41g, 63mmol) in 30ml dry dichloromethane and the mixture was stirred at 5C for 1h under Argon. The solution of aluminum chloride: acid chloride complex was added dropwise over 30min to a solution of ferrocene (11.16g, 60mmol) in 100ml dry dichloromethane at 0C. The reaction mixture was warmed to room temperature and stirred for 16h. A solution of NaBH4 (2.38g, 63mmol) in 25ml diglyme was added dropwise to the purple reaction mixture at-5C. An orange solution was formed and stirred at 0C for 1h. The mixture was then hydrolyzed with addition of 20ml water while maintaining its temperature at less than or equal to 10C. The mixture was allowed to separate by settling and the organic phase was then withdrawn. The aqueous phase was extracted with 3 times 30ml of dichloromethane and then all the organic phases are combined. Combined organic layer was washed with 50ml of brine and then dichloromethane was distilled under atmospheric pressure. The diglyme and the residual ferrocene which was found to be entrained by the diglyme were then distilled at reduced pressure approximately 20mm Hg and a column head temperature of 85-95C. The alkylferrocene derivatives were distilled at a more reduced pressure, less than 5mm Hg.

With the rapid development of chemical substances, we look forward to future research findings about Ferrocene

Reference£º
Article; Teimuri-Mofrad, Reza; Safa, Kazem D.; Rahimpour, Keshvar; Journal of Organometallic Chemistry; vol. 758; (2014); p. 36 – 44;,
Iron Catalysis in Organic Synthesis | Chemical Reviews
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion