Conditions | Yield |
---|---|
Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 0℃; for 0.25h; Stage #2: ferrocene at 20℃; Inert atmosphere; | 98% |
With phosphorus oxychloride In neat (no solvent) anilide and P-compd. stirring at room temp. for 30 min, Fe-compd. addn.,mixt. stirring at room temp. for 3 d, quenching by pouring onto ice, aq . layer extn. after 2 h with Et2O, org. layer drying (MgSO4), vac. concn.; residue flash column chromy. (SiO2, petrol/E2O 7:3 to 5:5), recrystn. (hot petroleum); | 87% |
With trichlorophosphate In neat (no solvent) Vilsmeyer formylation; double mol amt. of formylation mixt., few days at ambient temp.;; | 81% |
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
With sodium hydride; sodium iodide In tetrahydrofuran at 40℃; chemoselective reaction; | 94% |
1-ferrocenylmethanol
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
With ferrocene-labeled Merrifield resin-supported ionic liquid ([FemDMMerA]RuO4) In tetrahydrofuran for 4h; Reflux; Green chemistry; | 92% |
With C34H37N4O6Ru2(1+)*Cl(1-); potassium hydroxide In toluene at 70℃; for 6h; Schlenk technique; Inert atmosphere; | 90% |
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-tetramethyl-piperidine-N-oxyl; TPGS-750-M; copper(I) bromide In water at 20℃; for 24h; | 88% |
ferrocene
N,N-dimethyl-formamide
A
ferrocenecarboxaldehyde
B
1,1'-ferrocenyldicarboxaldehyde
Conditions | Yield |
---|---|
With tert.-butyl lithium In tetrahydrofuran; n-heptane under N2; tBuLi in hexane is added to ferrocene in THF at -20°C, stirred for 30 min, DMF is added at -10°C, HCl is added; extd. with CH2Cl2, chromd. (SiO2, CH2Cl2); | A 91% B 1% |
With potassium tert-butylate; tert.-butyl lithium In tetrahydrofuran N2-atmosphere; dropwise addn. of t-BuLi to mixt. of ferrocene and t-BuOKat -74 to -70°C, stirring at -74°C for 1 h, addn. of exce ss DMF, warming to -40°C over 20 min; water addn., solvent removal (reduced pressure), extn. into CH2Cl2, drying (MgSO4), chromy. (SiO2, hexane, then CH2Cl2, then CH2Cl2/Et2O=1:1); | A 90.7% B 4.9% |
Stage #1: ferrocene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at -80 - 0℃; for 0.25h; Stage #2: N,N-dimethyl-formamide In n-heptane at -80℃; for 2h; | A 20% B 71% |
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.25h; Inert atmosphere; Stage #2: ferrocene at 40℃; for 3h; Inert atmosphere; | 90% |
With trichlorophosphate In chloroform at -10℃; for 13.5h; Vilsmeier Reaction; Reflux; | 79% |
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at -10 - -5℃; Inert atmosphere; Stage #2: ferrocene In chloroform at 20℃; Inert atmosphere; | 79% |
Conditions | Yield |
---|---|
In diethyl ether Ar; pptn. on mixing; filtration, evapn. of soln.; | A 90% B n/a |
Conditions | Yield |
---|---|
In diethyl ether Ar; pptn. on mixing; filtration, evapn. of soln.; | A 90% B n/a |
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
With [RhCl2(p-cymene)]2; copper diacetate In tert-Amyl alcohol at 80℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; | 75% |
With ferrocene; copper diacetate In 1,2-dichloro-ethane at 80℃; Reagent/catalyst; | 50% |
Conditions | Yield |
---|---|
With trichlorophosphate for 72h; | 73% |
Conditions | Yield |
---|---|
In dichloromethane presence of AlCl3, Cl2CHOC2H5 excess, 0°C;; | 72% |
tert.-butyl lithium
A
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: ferrocenecarboxaldoxime; tert.-butyl lithium In diethyl ether at -80℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: With C20H34ClO3P In diethyl ether at -30 - 20℃; for 18h; Inert atmosphere; Schlenk technique; | A 8% B 72% C 3% |
Conditions | Yield |
---|---|
With AlCl3 In dichloromethane triethyl orthoformate added dropwise to mixt. of ferrocene and CH2Cl2 under stirring, after complete dissolution of ferrocene anhydrous AlCl3 slowly added, mixt. stirred at room temp. for 3 h; quenched with satd. soln. of sodium hydrosulfite, extraction with Et2O, extract concd. under vac., chromy. (silica gel, petroleum ether/ethyl acetate (5/1)); | 70% |
With aluminum (III) chloride In dichloromethane at 20℃; for 4h; | 70% |
With aluminum (III) chloride In benzene at 0 - 25℃; |
ferrocenyl-pentacarbonylmanganese
A
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
With methanol In methanol under N2, soln. of Mn(CO)5(CpFeC5H4) in MeOH stirred at room temp. for 67 h; evapd., extd. with pentane, evapd., taken up in CH2Cl2, sepd. by columnchromy. (Kieselgel, CH2Cl2); | A <1 B 69% |
A
ferrocenecarboxaldehyde
B
(Sp,Sp)-[1,1'-biferrocenyl]-2,2'-dicarboxaldehyde
Conditions | Yield |
---|---|
With copper at 105℃; Inert atmosphere; Darkness; | A n/a B 66.8% C n/a |
A
ferrocenecarboxaldehyde
B
1-ferrocenylmethanol
Conditions | Yield |
---|---|
With sodium azide In water boiling; | A 2% B 8.6% C 62% |
With NaN3 In water boiling; | A 2% B 8.6% C 62% |
cis-bis(benzonitrile)dichloroplatinum(II)
A
ferrocenecarboxaldehyde
[Pt([(η5-C5H3)-CH=N-(C6H4-2-SMe)]Fe(η5-C5H5))Cl]
Conditions | Yield |
---|---|
In toluene suspn. of Pt complex in toluene heated under reflux until solid dissolved, filtered, filtrate treated with Fe complex, mixt. heated under refluxfor 5.5 h; evapd. under vac., residue washed with hexane, dissolved in CH2Cl2, hexane added, slowly evapd. at room temp., crystals collected, air-dried; elem. anal.; | A n/a B 59% |
η-fluorene-η-cyclopentadienyliron(II) hexafluorophosphate
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
With t-BuOK; n-BuLi In tetrahydrofuran; hexane dropwise addn. of BuLi (2.5 M, hexane, 1 h) to soln. (THF) of Cp-deriv. (-78°C), mixing with soln. (THF) of Fe-intermediate (made from t-BuOK and Fe-compd., 0°C, 30 min), heating (60°C, 6 h); cooling to room temp. extn. (hexane-water (+ HCl drop)), org. phase drying (MgSO4), concg., chromy. (SiO2, hexane); | 56% |
6-(dimethylamino)fulvene
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane Irradiation (UV/VIS); a stirred soln. of Fe-complex and pentafulvene in CH2Cl2 was irradiated for 14 h with a 300-W sunlamp (Osram) in an atm. of N2, cooled to room temp., filtered, EtOH and 2 N NaOH were added, stirring was continued for another 90 min; layers were sepd., aq. layer dild., extd. with CH2Cl2, combined org. layers were washed twice with water, dried (Na2SO4), concd., residue was chromd. over alumina column (B II), recrystd. from ether-hexane or sublimed at 0.001 Torr; | 53% |
lithium aluminium tetrahydride
1-ferrocenoyl-1H-imidazole
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
In diethyl ether (Ar or N2); addn. of iron complex to Et2O with LiAlH4, stirring for 15 min at room temp.; addn. to a mixt. of cold water and ethyl acetate, extn. with Et2O, drying (Na2SO4), evapn., column chromy. (Al2O3, petroleum ether/Et2O 10:1), evapn.; | 52% |
carbon dioxide
A
ferrocenecarboxaldehyde
B
(Sp)-2-formylferrocene-1-carboxylic acid
Conditions | Yield |
---|---|
With t-butyl lithium; hydrochloric acid; SnCl2 In diethyl ether; water; pentane Schlenk techniques used under Ar, Fc(C4H6O2)CH2OMe (20 mmol) in Et2O treated with 1.7M pentane soln. of tBuLi (22 mmol) at -78°C for 10 min, stirred for 1 h at room temp., cooled to -20°C, CO2 gas introduced for 20 min, aq. HCl/SnCl2 added; stirred overnight at room temp., organic phase sepd., aq. phase extd. with EtOAc, combined organic phase washed with H2O, dried over Na2SO4, evapd., chromd. (SiO2, CH2Cl2/MeOH (80:1, 30:1)), evapd., petroleum ether added, filtered, dried; elem. anal.; | A 18% B 52% |
diiron nonacarbonyl
1-ferrocenylmethanol
A
ferrocenecarboxaldehyde
B
bis(ferrocenylmethyl)ether
Conditions | Yield |
---|---|
In benzene soln. of ferrocenylcarbinol is degassed (N2) and refluxed for 30 h in presence of Fe2(CO)9; react. mixt. is filtered over Celite, concd. and chromatographed (silica gel 60, CH2Cl2); | A 20% B 51% |
water
A
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
With K3Fe(CN)6/K2CO3; hydroquinidine 2,5-Ph2-4,6-pyrimidinediyl diether; K2OsO2(OH)4 In water; tert-butyl alcohol (N2); solid Os complex (0.2 equiv.) was added to soln. of K3Fe(CN)6 (6 equiv.), K2CO3 (6 equiv.) and hydroquinidine compd. (0.2 equiv.) in t-BuOH/H2O; mixt. was stirred for 2 h; ferrocenyl complex was added over 1.5 h; stirred at room temp. for 66 h; Na2SO3 added; extd. (EtOAc); org. extracts washed (brine) and dried (Na2SO4); evapd. (vac.); chromd. (SiO2, C6H14/EtOAc); elem. anal.; | A 20% B 51% |
With K3Fe(CN)6/K2CO3; hydroquinidine 2,5-Ph2-4,6-pyrimidinediyl diether; K2OsO2(OH)4 In water; acetonitrile (N2); solid Os complex (0.1 equiv.) was added to soln. of K3Fe(CN)6 (3 equiv.), K2CO3 (3 equiv.) and hydroquinidine compd. (0.1 equiv.) in CH3CN/H2O; mixt. was stirred for 2 h; ferrocenyl complex was added over 1.5 h; stirred at room temp. for 110 h; Na2SO3 added; extd. (EtOAc); org. extracts washed (brine) and dried (Na2SO4); evapd. (vac.); chromd. (SiO2, C6H14/EtOAc); | A 4% B 30% |
ferrocenyl-pentacarbonylmanganese
A
ferrocene
B
ferrocenecarboxaldehyde
C
1-ferrocenylmethanol
Conditions | Yield |
---|---|
With propene; carbon monoxide; hydrogen In N,N-dimethyl-formamide High Pressure; soln. of Mn(CO)5(CpFeC5H4) in DMF pressurised in autoclave successivelywith 8 bar of propene, 15 bar of CO, and 15 bar of H2, stirred at 100°C for 20 h; evapd. in vac., extd. with CH2Cl2, sepd. by preparative thin layer chromy. (CH2Cl2); | A n/a B 17% C 47% |
water
A
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
With K3Fe(CN)6/K2CO3; hydroquinine 2,5-Ph2-4,6-pyrimidinediyl diether; K2OsO2(OH)4 In water; tert-butyl alcohol (N2); solid Os complex (0.2 equiv.) was added to soln. of K3Fe(CN)6 (6 equiv.), K2CO3 (6 equiv.) and hydroquinine compd. (0.2 equiv.) in t-BuOH/H2O (1/1); mixt. was stirred for 2 h; ferrocenyl complex was added over 1.5 h; stirred at room temp. for 47 h; Na2SO3 added; extd. (EtOAc); org. extracts washed (brine) and dried (Na2SO4); evapd. (vac.); chromd. (SiO2, C6H14/EtOAc); | A 26% B 47% |
With K3Fe(CN)6/K2CO3; hydroquinine 1,4-phthalazinediyl diether; K2OsO2(OH)4 In water; acetonitrile (N2); solid Os complex (0.1 equiv.) was added to soln. of K3Fe(CN)6 (3 equiv.), K2CO3 (3 equiv.) and hydroquinine compd. (0.1 equiv.) in CH3CN/H2O (1/1); mixt. was stirred for 2 h; ferrocenyl complex was added over 1.5 h; stirred at room temp. for 44 h; Na2SO3 added; extd. (EtOAc); org. extracts washed (brine) and dried (Na2SO4); evapd. (vac.); chromd. (SiO2, C6H14/EtOAc); | A n/a B 10% |
sodium tetrahydroborate
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
In tetrahydrofuran N2 atmosphere; addn. of NaBH4 (0°C), stirring (room temp., 3 h); H2O addn., extn. (hexane), drying (Na2SO4), filtration, evapn., extn. (hexane), chromy. (SiO2, CH2Cl2); | 43% |
ethanol
water
1,1-dimethylguanidine dihydrogensulfate
A
ferrocenecarboxaldehyde
B
6-amino-2-ethoxy-4-ferrocenyl-5-ferrocenylmethyl-4,5-dihydropyridine-3,5-dicarbonitrile
C
2-amino-6-ethoxy-4-ferrocenylpyridine-3,5-dicarbonitrile
D
4-amino-2-dimethylamino-6-ferrocenylpyrimidine-5-carbonitrile
Conditions | Yield |
---|---|
With sodium carbonate at 80℃; for 8h; | A 10% B 15% C 23% D 42% |
ferrocenyl-pentacarbonylmanganese
acetonitrile
A
ferrocene
B
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
In acetonitrile under N2, soln. of Mn(CO)5(CpFeC5H4) in MeCN stirred for 63 h at room temp.; filtered through Na2SO4, evapd., extd. with pentane, concd., chromd. (Kieselgel; pentane, CH2Cl2, Et2O); | A n/a B 37% |
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
With hexamethylenetetramine In acetic acid boiling; | 37% |
With hexamethylenetetramine In acetic acid boiling; | 37% |
ethanol
water
benzamidine monohydrochloride
A
ferrocenecarboxaldehyde
B
6-amino-2-ethoxy-4-ferrocenyl-5-ferrocenylmethyl-4,5-dihydropyridine-3,5-dicarbonitrile
D
2-amino-6-ethoxy-4-ferrocenylpyridine-3,5-dicarbonitrile
Conditions | Yield |
---|---|
With sodium carbonate at 80℃; for 8h; | A 11% B 12% C 33% D 22% E 9% |
ethanol
water
acetamidine hydrochloride
A
ferrocenecarboxaldehyde
B
6-amino-2-ethoxy-4-ferrocenyl-5-ferrocenylmethyl-4,5-dihydropyridine-3,5-dicarbonitrile
C
6-amino-4-ferrocenyl-2-methyl-3,4-dihydropyrimidine-5-carbonitrile
D
2-amino-6-ethoxy-4-ferrocenylpyridine-3,5-dicarbonitrile
E
4-amino-6-ferrocenyl-2-methylpyrimidine-5-carbonitrile
Conditions | Yield |
---|---|
With sodium carbonate at 80℃; for 8h; | A 9% B 14% C n/a D 27.5% E 10% |
Conditions | Yield |
---|---|
lithium perchlorate In dichloromethane (Ar); mixt. of Fe complex and LiClO4 (2 equiv.) in CH2Cl2 was stirred for 3 min; amine was added via syringe; after 5 min Me3SiCN was added; mixt. was stirred at room temp. for 20-30 min; CH2Cl2 added; filtered; org. layer washed (aq. NaHCO3, H2O); dried (Na2SO4); solvent removed; chromd. (silica gel, petroleum ether/EtOAc); | 100% |
pyrrolidine
ferrocenecarboxaldehyde
trimethylsilyl cyanide
[(C5H5)Fe(C5H4CH(CN)NC4H8)]
Conditions | Yield |
---|---|
lithium perchlorate In dichloromethane (Ar); mixt. of Fe complex and LiClO4 (2 equiv.) in CH2Cl2 was stirred for 3 min; amine was added via syringe; after 5 min Me3SiCN was added; mixt. was stirred at room temp. for 20-30 min; CH2Cl2 added; filtered; org. layer washed (aq. NaHCO3, H2O); dried (Na2SO4); solvent removed; chromd. (silica gel, petroleum ether/EtOAc); | 100% |
Conditions | Yield |
---|---|
lithium perchlorate In dichloromethane (Ar); mixt. of Fe complex and LiClO4 (2 equiv.) in CH2Cl2 was stirred for 3 min; amine was added via syringe; after 5 min Me3SiCN was added; mixt. was stirred at room temp. for 20-30 min; CH2Cl2 added; filtered; org. layer washed (aq. NaHCO3, H2O); dried (Na2SO4); solvent removed; chromd. (silica gel, petroleum ether/EtOAc); | 100% |
Conditions | Yield |
---|---|
lithium perchlorate In dichloromethane (Ar); mixt. of Fe complex and LiClO4 (2 equiv.) in CH2Cl2 was stirred for 3 min; amine was added via syringe; after 5 min Me3SiCN was added; mixt. was stirred at room temp. for 20-30 min; CH2Cl2 added; filtered; org. layer washed (aq. NaHCO3, H2O); dried (Na2SO4); solvent removed; chromd. (silica gel, petroleum ether/EtOAc); | 100% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 16h; Inert atmosphere; Schlenk technique; Reflux; | 100% |
With sodium acetate In ethanol; water under N2; H2NOH*HCl (2 equiv.) in water added to Fe complex in EtOH; AcONa (3 equiv.) added; refluxed for 3 h; cooled; concd. in vac.; CHCl3 added dropwise; stirred for 0.5 h; according to K. Schoegl, et al., Monatsh. Chem. 97 (1966) 150; filtered; filtrate concd. under vac.; | 95.8% |
With sodium hydroxide In ethanol for 3h; Reflux; | 92% |
Conditions | Yield |
---|---|
In methanol in CH3OH/piperidine; | 100% |
In methanol in CH3OH/piperidine; | 100% |
With dichloro[2,6-bis(4-isopropyloxazolin-2-yl)pyridine]zinc In water at 20℃; for 0.05h; Catalytic behavior; Reagent/catalyst; Solvent; Knoevenagel Condensation; Inert atmosphere; Schlenk technique; | 99% |
ferrocenecarboxaldehyde
(R)-1-phenyl-ethyl-amine
Conditions | Yield |
---|---|
With MgSO4 In tetrahydrofuran (Ar) soln. ferrocenecarboxaldehyde and (R)-1-phenylethylamine in THF wasstirred at room temp. over MgSO4 for 24 h; soln. was filtered through Celite and evapd. in vacuo; | 100% |
In methanol the mixt. in methanol was stirred for 20 h at room temp.; evapd., the solid was dissolved in benzene and pptd. with hexane; elem. anal.; | 90% |
In methanol in presence of molecular sieves under Ar at room temp.; GC; solvent emoved in vacuo; recrystd. from Et2O; | 78% |
In methanol Fe compd. reacted with org. compd. in MeOH according to Wang, H. X. et al., Inorg. Chem. Commun. 9 (2006) 658; Wang, H. X. et al., Polyhedron 25(2006) 2530; Wang, H. X. et al., Inorg. Chim. Acta 359 (2006) 4114; elem. anal.; | 75% |
In chloroform for 3h; Reflux; |
Conditions | Yield |
---|---|
With pyrrolidine In neat (no solvent) at 20℃; for 0.116667h; Aldol Condensation; | 100% |
ferrocenecarboxaldehyde
2,4,6-trimethylaniline
Conditions | Yield |
---|---|
In chloroform soln. of Fe-complex and ligand in CHCl3 was heated under reflux, cooled to room temp.; solvent was evapd., dried under vac.; elem. anal.; | 99.62% |
With toluene-4-sulfonic acid In toluene Reflux; Dean-Stark; | 90% |
In chloroform refluxing (6 h); removal of solvent, trituration with hexane; | 82% |
In ethanol boiling; | |
In toluene for 8h; Inert atmosphere; Reflux; Molecular sieve; |
ferrocenecarboxaldehyde
N,N-dimethylammonium chloride
sodium tris(acetoxy)borohydride
N,N-dimethylaminomethylferrocene
Conditions | Yield |
---|---|
With triethylamine In dichloromethane Fe complex reacted with HNMe2*HCl and B compd. in presence of Et3N in CH2Cl2; | 99% |
ferrocenecarboxaldehyde
ethylenediamine
N,N'-bis(ferrocenylmethylene)ethylenediamine Schiff base
Conditions | Yield |
---|---|
In neat (no solvent, solid phase) Fe complex (2 equiv.) and ligand were ground at room temp.; kept in vac.overnight; recrystd. (cold MeOH); | 99% |
With potassium carbonate In ethanol reaction in boiling absolute EtOH in the presence of anhydrous K2CO3 under N2 and with protection from light; recrystn. from EtOH; elem. anal.; | 87% |
In ethanol Inert atmosphere; Schlenk technique; | 87% |
lithium aluminium tetrahydride
ferrocenecarboxaldehyde
1-ferrocenylmethanol
Conditions | Yield |
---|---|
In diethyl ether under Ar; LiAlH4 in anhyd. Et2O added dropwise to Fe complex in anhyd. Et2O; stirred at room temp. for 30 min; aq. soln. of NH4Cl slowly added; ether phase sepd.; aq. phase extd. withEt2O; combined org. phases washed with H2O and brine; dried over Na2SO4 ; filtrate evapd. under vac.; | 99% |
In not given |
sodium tetrahydroborate
ferrocenecarboxaldehyde
1-ferrocenylmethanol
Conditions | Yield |
---|---|
In methanol; sodium hydroxide aq. NaOH; (N2); a soln. of NaBH4 in aq. NaOH added to a MeOH soln. of Fe complex at 0°C, stirred and allowed to warm to room temp. overnight; evapd., extd. (Et2O), the org. layer washed (H2O), dried (MgSO4), filtered, evapd. (vac.); | 99% |
With H2O In ethanol | 95% |
In methanol synthesized by Broadhead, G. D., Osgerby, J. M., Pauson, P. L., J. Chem.Soc. (1958) 650; | 90% |
In ethanol synthesized by Broadhead, G. D., Osgerby, J. M., Pauson, P. L., J. Chem.Soc. (1958) 650; | 90% |
ferrocenecarboxaldehyde
1-ferrocenylmethanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 0 - 20℃; Inert atmosphere; | 99% |
With C46H49CoN3P4(2+)*2BF4(1-); hydrogen; potassium hydroxide In ethanol; acetonitrile at 60℃; under 22801.5 Torr; for 24h; Autoclave; Glovebox; chemoselective reaction; | 98% |
With lithium aluminium tetrahydride at 45℃; for 2h; Inert atmosphere; Reflux; | 97% |
lithium aluminium tetrahydride
ferrocenecarboxaldehyde
cyclopenta-1,3-diene
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol cyclopentadiene (ca.250 mmol) was added to a soln. of KOH (153 mmol) in ethanol; the mixt. was added to a stirred soln. of Fe-contg. compd (44 mmol) in ethanol; after 2.5 h TLC showed the react. completness; LiAlH4 (44 mmol) in Et2O was added; after 20 h the ppt. was collected on a frit, washed with Et2O and dried for 24 h in a vac.; | A 99% B 80% |
Conditions | Yield |
---|---|
With iodine In chloroform for 1h; | 99% |
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 10h; Schlenk technique; Sealed tube; Inert atmosphere; | 95.2% |
presence of acidic catalysts: HCl, ZnCl2, p-CH3C6H4SO3H or BF3*O(C2H5)2; | 93% |
presence of acidic catalysts: HCl, ZnCl2, p-CH3C6H4SO3H or BF3*O(C2H5)2; | 93% |
With toluene-4-sulfonic acid In toluene at 60℃; for 24h; | 76% |
Conditions | Yield |
---|---|
In pyridine standing of a soln. of ferrocene-compd. and hydroxylamine hydrochloridein dry pyridine at room temp. for 24 h under N2; pouring into water, pptn., recrystn. from MeOH; | 99% |
Conditions | Yield |
---|---|
In chloroform byproducts: water; refluxing aldehyde and amine for 3 h, evapn. (reduced pressure), dissoln. in MeOH, addn. of excess NaBH4 (in portions, 0°C), stirring for30 min; addn. of aq. NaOH. extn. into CHCl3, drying, evapn.; elem. anal.; | 99% |
ferrocenecarboxaldehyde
trimethylsilyl cyanide
Conditions | Yield |
---|---|
With C29H38AlN4O2(1+)*CF3O3S(1-) In tetrahydrofuran at 20℃; for 0.416667h; Catalytic behavior; Inert atmosphere; Schlenk technique; | 99% |
With zinc(II) iodide In neat (no solvent) under N2; mixt. stirred overnight; evapd., column chromy. (alumina, hexane/CH2Cl2 75:25), recrystd. (hexane/CH2Cl2); elem. anal.; | 61% |
sodium tetrahydroborate
ferrocenecarboxaldehyde
para-methylbenzylamine
Conditions | Yield |
---|---|
In chloroform byproducts: water; refluxing aldehyde and amine for 3 h, evapn. (reduced pressure), dissoln. in MeOH, addn. of excess NaBH4 (in portions, 0°C), stirring for30 min; addn. of aq. NaOH. extn. into CHCl3, drying, evapn.; elem. anal.; | 99% |
ferrocenecarboxaldehyde
ethylenediamine
Conditions | Yield |
---|---|
In benzene byproducts: H2O; Fe complex added to a soln. of ethylenediamine, refluxed overnight with a Dean-Stark apparatus for azeotropic distn.; evapd. (vac.); elem. anal.; | 99% |
In not given byproducts: H2O; Fe complex reacted with H2NCH2CH2NH2 using Dean-Stark apparatus for removal of H2O by azeotropic distn.; |
Conditions | Yield |
---|---|
With potassium carbonate In neat (no solvent) stirring (darkness); hexane and K2CO3 addn., filtn., concn.; elem. anal.; | 99% |
ferrocenecarboxaldehyde
(1S,2R)-2-amino-1-phenylpropane-1,3-diol
Conditions | Yield |
---|---|
With potassium carbonate In neat (no solvent) stirring (darkness); hexane and K2CO3 addn., filtn., concn.; elem. anal.; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In neat (no solvent) stirring (darkness); hexane and K2CO3 addn., filtn., concn.; elem. anal.; | 99% |
ferrocenecarboxaldehyde
4-Nitrophenylacetonitrile
Conditions | Yield |
---|---|
With piperidine In neat (no solvent, solid phase) (under N2, Schlenk); Fe-complex and ligand added to tube, mixed, piperidine added, mixed at room temp., sealed, shaken for 30 min at room temp.; dried in air overnight, column chromy. with hexane/Et2O (4:1); elem. anal.; | 99% |
Conditions | Yield |
---|---|
99% |
ferrocenecarboxaldehyde
(S)-(+)-2-amino-1-methoxy-3-phenylpropane hydrochloride
Conditions | Yield |
---|---|
With potassium carbonate In neat (no solvent) standing (darkness), stirring; K2CO3 and hexane addn., filtn., evapn. (vac.), recrystn.; elem. anal.; | 99% |
ferrocenecarboxaldehyde
diethyl [(4-cyanophenyl)methyl]phosphonate
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; for 2h; Darkness; | 99% |
4-methoxy-5H-furan-2-one
ferrocenecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-methoxy-5H-furan-2-one With n-butyllithium Stage #2: ferrocenecarboxaldehyde In tetrahydrofuran at -78 - 20℃; | 99% |
Stage #1: 4-methoxy-5H-furan-2-one With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; Stage #2: ferrocenecarboxaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Further stages; | 95% |
ferrocenecarboxaldehyde
4-Chloro-5-hydrazino-2-methyl-3(2H)-pyridazinone
Conditions | Yield |
---|---|
In ethanol Reflux; Inert atmosphere; | 99% |
Molecule structure of Ferrocenecarboxaldehyde (CAS NO.12093-10-6):
IUPAC Name: Cyclopenta-1,3-diene; cyclopenta-2,4-dien-1-ylidenemethanolate; iron(2+)
Molecular Weight: 214.0415 g/mol
Molecular Formula: C11H10FeO
Melting Point: 118-120 °C(lit.)
Flash Point: 98.8 °C
Enthalpy of Vaporization: 52.33 kJ/mol
Boiling Point: 213.6 °C at 760 mmHg
Vapour Pressure: 0.036 mmHg at 25 °C
Water Solubility: insoluble
Stability: Stable. Incompatible with strong oxidizing agents.
H-Bond Acceptor: 2
Exact Mass: 214.008107
MonoIsotopic Mass: 214.008107
Topological Polar Surface Area: 23.1
Heavy Atom Count: 13
Canonical SMILES: [CH-]1C=CC=C1.C1=CC(=C[O-])C=C1.[Fe+2]
InChI: InChI=1S/C6H6O.C5H5.Fe/c7-5-6-3-1-2-4-6;1-2-4-5-3-1;/h1-5,7H;1-5H;/q;-1;+2/p-1
InChIKey: HEWFKXVSWQSSAT-UHFFFAOYSA-M
EINECS: 235-158-1
Product Categories: Aromatic Aldehydes & Derivatives (substituted); Ferrocene series
Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
Ferrocenecarboxaldehyde (CAS NO.12093-10-6) is also named as 2-Ferrocenecarboxaldehyde ; Cyclopentadienecarboxaldehyde, cyclopentadienyliron deriv. ; Ferrocene, formyl- ; Ferrocenealdehyde ; Ferrocenecarbaldehyde ; Formyldicyclopentadienyliron ; Formylferrocene ; Iron, pi-cyclopentadienyl(formyl-pi-cyclopentadienyl)- ; NSC 407052 . Ferrocenecarboxaldehyde (CAS NO.12093-10-6) is crystalline solid.
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