1277-49-2

Usage

Uses

1. Used in Chemical Synthesis:
1-(Ferrocenyl)ethanol is used as a ligand in titanium-catalyzed intermolecular hydroamination of terminal alkynes, which is crucial for controlling the Markovnikov vs. anti-Markovnikov addition in chemical reactions.
2. Used in Polymer Chemistry:
It serves as a reactant for single-electron transfer living radical polymerization reactions, which is essential for the controlled synthesis of polymers with specific structures and properties.
3. Used in Pharmaceutical Industry:
1-(Ferrocenyl)ethanol is used as a reactant for the preparation of ferrocene-modified thiopyrimidines, which are potential anticancer agents. These compounds have shown promise in targeting cancer cells and inhibiting their growth.
4. Used in Materials Science:
In the field of materials science, 1-(Ferrocenyl)ethanol is used for the preparation of reversible addition-fragmentation chain transfer (RAFT) agents. These agents are crucial for the RAFT polymerization of styrene, a process that produces polymers with well-defined structures and properties.
5. Used in Catalyst Design:
The unique properties of 1-(Ferrocenyl)ethanol make it a valuable component in the design of catalysts for various industrial applications, including the production of fine chemicals and pharmaceuticals.

Synthetic route

acetylferrocene (1271-55-2) → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C39H45FeN2O2PS; hydrogen; sodium methylate In methanol at 40℃; for 12h; Reagent/catalyst; Solvent; Autoclave; Large scale;	99%
With LiAlH4 In diethyl ether LiAlH4 (10.54 mmol) added in portion to soln. of acetylferrocene (4.38 mmol) (0°C) under N2; stirred (room temp., 3 h);; cooled to 0°C; H2O added; ether added; org. layer sepd.; aq. layer extd. with ether; combined org. layers dried over Na2SO4; filtered; concd.;	97%
With potassium tert-butylate; hydrogen; tetracarbonyl(2-(diphenylphosphino)-ethylamine)chromium(0) In diethylene glycol dimethyl ether at 120℃; under 37503.8 Torr; for 14h; Autoclave;	97%

ferrocenecarboxaldehyde (12093-10-6) → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With LiAlH4 In diethyl ether Ar-atmosphere; addn. of acetylferrocene to excess LiAlH4 (15-20°C, stirring); addn. of satd. aq. NH4Cl (cooling to 0-5°C), washing of org. layer (water), drying (Na2SO4), solvent removal;	93%

acetylferrocene (1271-55-2) + water (7732-18-5) → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With samarium diiodide In tetrahydrofuran N2-atmosphere; molar ratio SmI2:ferrocene derivative:water=2.6:1:11, 25°C, 10 min; addn. of ice water, filtration over SiO2, concn.;	92%

ferrocenecarboxaldehyde (12093-10-6) → vinyl ferrocene (1271-51-8) + 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With methylmagnesium bromide In not given Wittig reaction;;	A 6% B 90%
With CH3MgBr In not given Wittig reaction;;	A 6% B 90%

methyl magnesium iodide (917-64-6) + ferrocenecarboxaldehyde (12093-10-6) → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
In diethyl ether reflux;	85.3%

lithium borohydride + acetylferrocene (1271-55-2) → vinyl ferrocene (1271-51-8) + 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
In methanol lithium borohydride (5.0 equiv.) added to a soln. of the ferrocenyl ketone (1.0 equiv.) in methanol, stirred at room temp. overnight (16 h), water added; extracted with ether, dried (MgSO4), concentrated in vacuo, crude product purified by flash column chromy. on silica gel (TLC Rf 0.66 (1:3 acetone-hexane)), elem. anal.;	A 2% B 77%

vinyl ferrocene (1271-51-8) → 1-ethylferrocene + 1-ferrocenylethanol (1277-49-2) + butane-2,3-diyldiferrocene + C5H5FeC5H4CH(CH3)OC2H5

Conditions	Yield
In ethanol Irradiation (UV/VIS); UV-photolysis in abs. ethanol; mechanism discussed;;	A 4% B 9% C 4% D 58%
In ethanol Irradiation (UV/VIS); UV-photolysis in abs. ethanol, presence of H2O; mechanism discussed;;	A n/a B 0% C n/a D n/a

acetylferrocene (1271-55-2) + (2,2'-bipyridyl)(tetrahydroborato)zinc → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
In acetonitrile addn. of Zn complex to soln. of ferrocene derivative in CH3CN at room temp., strirred for 45 min at room temp., addn. of soln. of FeCl3*6H2O, stirred for 20 min; extraction with CH2Cl2, dried (MgSO4), evapn. of solvent, chromy. (silica gel / CCl4/Et2O: 5/2);	50%

1-methoxyethyl ferrocene → acetylferrocene (1271-55-2) + vinyl ferrocene (1271-51-8) + 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With aluminum oxide In n-heptane ambient temp., neutral Al2O3;;	A 6% B 3% C 44%

lithium aluminium tetrahydride (16853-85-3) + acetylferrocene (1271-55-2) → vinyl ferrocene (1271-51-8) + 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
In tetrahydrofuran room temp., 16 h;

S-(1-ferrocenylethyl)thioglycolic acid + aniline (62-53-3) → 1-ferrocenylethanol (1277-49-2)

hydrogenchloride (7647-01-0) + (C5H5)Fe(C5H4CH(CH3)OCH2COOCH3) (191876-57-0) → 1-ferrocenylethanol (1277-49-2) + α,α'-diferrocenyldiethyl ether

Conditions	Yield
In diethyl ether addn. of aq. HCl (1:1) to Fe-complex soln., stirring (room temp., 24 h); TLC (SiO2); product mixt. not sepd., detd. by NMR spectroscopy;

sodium tetrahydroborate (16940-66-2) + acetylferrocene (1271-55-2) → vinyl ferrocene (1271-51-8) + 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
In methanol room temp., 16 h;

(C5H5)Fe(C5H4CH(CH3)N(CH3)3)(1+)*I(1-)=[(C5H5)Fe(C5H4CH(CH3)N(CH3)3)]I → vinyl ferrocene (1271-51-8) + 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
In water decompn. in H2O at 20-40°C;;	A <1 B n/a
In water decompn. in H2O at 20-40°C;;	A <1 B n/a

hydrogen azide + vinyl ferrocene (1271-51-8) → acetylferrocene (1271-55-2) + 1-ferrocenylethanol (1277-49-2) + 1-ferrocenylethyl acetate + 1-azido-ethylferrocene

Conditions	Yield
With acetic acid In benzene
With CH3COOH In benzene

fc-CHCl(CH3) → acetylferrocene (1271-55-2) + vinyl ferrocene (1271-51-8) + 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With water In water reaction with Na at -78°C or with Mg at -10°C, hydrolysis at ambient temp.; yield of products depends on conditions;;

fc-CHCl(CH3) → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With water; sodium carbonate In water -78°C;;

{C5H5FeC5H4CHCH3}(1+)*BF4(1-)={C5H5FeC5H4CHCH3}BF4 → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With hydroxide In water alkaline hydrolysis;;
With OH(1-) In water alkaline hydrolysis;;

C5H5FeC5H4C(CH3)N2 → acetylferrocene (1271-55-2) + vinyl ferrocene (1271-51-8) + 1-ferrocenylethanol (1277-49-2) + 1,2-diferrocenyl-1-methyl cyclopropane + (C10H9FeCH(CH3)N)2

Conditions	Yield
In benzene
In benzene
In benzene

(C5H5)Fe(C5H4CH(CH3)N(CH3)3)(1+)*I(1-)=[(C5H5)Fe(C5H4CH(CH3)N(CH3)3)]I → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With water In water
With water In tetrahydrofuran; water Kinetics; 50°C, 50 Vol.-% H2O;
With H2O In water; acetone Kinetics; 10-40 Vol.-% H2O, 50°C;

sodium dicarbonyl(cyclopentadienyl)ferrate + fc-CO-CH2-Fe(CO)2C5H5 → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2;
byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2;

fc-CO-CH2-Fe(CO)2C5H5 → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With lithium aluminium tetrahydride byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2;
With LiAlH4 byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2;

C10H9FeCH(CH3)OSO2F → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With water

(+)-(R)-C10H9FeCH(CH3)-S-CS-S-CH3 → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With LiAlH4 11-28 % retention of configuration;
With LiAlH4 In diethyl ether addn. of LiAlH4 to starting complex soln. in diethyl ether at 0°C under N2, reaction for 1 h; addn. of dil. NaOH or water at 0 or 25°C;

fc-CHCH3-Zr(C5H5)2Cl → (μ-oxo)bis[chlorobis(cyclopentadienyl)zirconium(IV)] + 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With water In diethyl ether; water
With H2O In diethyl ether; water

ferrocenylmethyl acetate → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With methanol In methanol Kinetics; methanolysis at 0°C; IR;

4-(1-ferrocenylethoxy)-3-methoxybenzaldehyde → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With water In acetone byproducts: vanillin; heating in aq. acetone;	>99

4-(1-ferrocenylethoxy)benzaldehyde → 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With silica gel In not given byproducts: p-hydroxybenzaldehyde; hydrolysis during an attempt of purification on a SiO2 column;	>99

(C6H5)CN4H(CH(CH3)(C5H4)Fe(C5H5))(1+)*BF4(1-)=[C6H5CN4H(CH(CH3)(C5H4)Fe(C5H5))]BF4 (207301-27-7) → 5-Phenyl-1H-tetrazole (18039-42-4) + 1-ferrocenylethanol (1277-49-2)

Conditions	Yield
With sodium hydroxide In water refluxing (5-10 min), cooling to 5 to 7°C; ppt. filtration off, washing (hot pentane), Fe-compd. obtaining from pentane extracts by drying, tetrazole remaining in the solid residue;

1-ferrocenylethanol (1277-49-2) + γ-cyclodextrin (17465-86-0, 130322-69-9, 130322-70-2) → α-hydroxyethylferrocene*γ-cyclodextrin

Conditions	Yield
In water molar ratio cyclodextrin : ferrocene = 1:2, addn. of crystals of ferrocene to an aq. soln. of cyclodextrin at 60°C with stirring; washed with water and THF, recrystn. from water or aq. alcohol; elem. anal.;	100%

1-ferrocenylethanol (1277-49-2) + β-cyclodextrin decahydrate → α-hydroxyethylferrocene*β-cyclodextrin*2H2O

Conditions	Yield
In water molar ratio cyclodextrin : ferrocene = 1:2, addn. of crystals of ferrocene to an aq. soln. of cyclodextrin at 60°C with stirring; washed with water and THF, recrystn. from water or aq. alcohol; elem. anal.;	100%

1-ferrocenylethanol (1277-49-2) + mercaptoacetic acid (68-11-1) → S-(1-ferrocenylethyl)thioglycolic acid

Conditions	Yield
With potassium hydroxide; trifluoroacetic acid In acetone addn. of 1.1 equiv. of mercapto-acid to Fe-complex soln., cooling to 0°C, addn. of CF3COOH, standing (room temp., overnight); addn. of 5% aq. KOH, treatment with CH2Cl2, addn. of few drops H3PO4 to aq. layer, extn. into CH2Cl2, shaking of extract with H2O, drying (MgSO4), evapn., recrystn. (hexane/C6H6 or EtOAc, not specified); elem. anal.;	99%
With ammonium cerium (IV) nitrate In nitromethane at 20℃; Inert atmosphere;	65%
With CF3COOH or CH3COOH	<=93

1-ferrocenylethanol (1277-49-2) + water (7732-18-5) → 1-ethylferrocene

Conditions	Yield
With samarium diiodide In tetrahydrofuran N2-atmosphere; molar ratio SmI2:ferrocene derivative:water=3.6:1:5.5, refluxing for 50 min; chromy. (SiO2, AcOEt/hexane=1:1); elem. anal.;	99%

1-ferrocenylethanol (1277-49-2) + acetic anhydride (108-24-7) → 1-ferrocenylethyl acetate

Conditions	Yield
With pyridine at 20℃; Inert atmosphere;	99%
With catalyst: DMAP In triethylamine acetic anhydride (196 mmol) and DMAP added to soln. of 1-ferrocenylethanol (38.5 mmol); stirred (room temp., 17 h); solvent removed; dild. with ether (200 ml) and H2O (100 ml); org. layer sepd.; dried over Na2SO4; filtered; concd.;	93%
With pyridine for 24h; Darkness;	76%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2.5h;

1-ferrocenylethanol (1277-49-2) + chloroformic acid ethyl ester (541-41-3) + aniline (62-53-3) → 1-[N-phenylamino]ethylferrocene + C5H5FeC5H4CH(CH3)OC2H5

Conditions	Yield
Stage #1: 1-ferrocenylethanol With n-butyllithium In tetrahydrofuran; hexane for 0.0833333h; Inert atmosphere; Stage #2: chloroformic acid ethyl ester In tetrahydrofuran; hexane for 0.0833333h; Inert atmosphere; Stage #3: aniline Further stages;	A 98% B n/a

1-ferrocenylethanol (1277-49-2) → vinyl ferrocene (1271-51-8)

Conditions	Yield
With copper(II) sulfate In toluene byproducts: H2O; in boiling toluene;;	97%
With potassium hydrogensulfate In benzene byproducts: H2O; in boiling benzene;;	90%
In neat (no solvent) byproducts: H2O; 210°C, 20 Torr;;	84%

1,2,3-Benzotriazole (95-14-7) + 1-ferrocenylethanol (1277-49-2) → 1-N-(1-ferrocenyl-1-methyl)ethylbenzotriazole (101006-59-1, 654083-40-6, 654083-57-5)

Conditions	Yield
With tetrafluoroboric acid In dichloromethane; water addn. of aq. HBF4 to a mixt. of iron complex and heterocycle in CH2Cl2, stirring for 5 min; addn. of Et2O, water, ascorbic acid, sepn., washing org. phase with coldwater, evapn. drying over CaCl2; elem. anal.;	97%
With HBF4 In dichloromethane treatment of 1-ferrocenylethanol with benzotriazole in CH2Cl2 in the presence of 45% aq. HBF4 at room temp. for several minutes ((J. Organomet. Chem. 580 (1999) 26);	93%
With tetrafluoroboric acid In dichloromethane 20°C;

1-ferrocenylethanol (1277-49-2) + N,N-Dimethyltrimethylsilylamine (2083-91-2) → trimethyl(α-ferrocenylethoxy)silane

Conditions	Yield
byproducts: (CH3)2NH; (Ar); mixing for 3 h at 80-90°C; fractionation under deep vac.; TLC; column chromy. (silica gel); elem. anal.;	96.5%

1-ferrocenylethanol (1277-49-2) + N,N-diethyl-1,1,1-trimethylsilanamine (996-50-9) → trimethyl(α-ferrocenylethoxy)silane

Conditions	Yield
byproducts: (C2H5)2NH; (Ar); mixing for 3 h at 80-90°C; fractionation under deep vac.; TLC; column chromy. (silica gel); elem. anal.;	96.5%

1-ferrocenylethanol (1277-49-2) + thiophenol (108-98-5) → (1-ferrocenylethyl) phenyl sulfide

Conditions	Yield
With CF3COOH or CH3COOH	96%
With tetrafluoroboric acid In dichloromethane; water at 20℃; for 0.0833333h;	83%

1-ferrocenylethanol (1277-49-2) + N,N-diethyl-1,1,1-trimethylsilanamine (996-50-9) → vinyl ferrocene (1271-51-8) + trimethyl(α-ferrocenylethoxy)silane

Conditions	Yield
In neat (no solvent) byproducts: (C2H5)2NH, H2O, (CH3)3SiOSi(CH3)3; under argon; equimolar amts of diethylaminotrimethylsilane and the Fe complex are heated to 80-90°C; reaction mixt. distd. under vac.; vinylferrocene recrystd. from hexane; products identified by chromy., IR, and mass spectrometry;	A 4% B 96%
In toluene byproducts: (C2H5)2NH, H2O, (CH3)3SiOSi(CH3)3; under argon; 0.131 mol of diethylaminotrimethylsilane and 0.048 mol of the Fe complex in toluene are heated for 4 h at 120-125°C while distilling off the liberated Et2NH; after cooling, the pptd. crystals of vinylferrocene are sepd.; filtrate distd. under vac.; vinylferrocene recrystd. from hexane; products identified by chromy., IR, and mass spectrometry;	A 83% B 17%
In neat (no solvent) byproducts: (C2H5)2NH, H2O, (CH3)3SiOSi(CH3)3; under argon; 0.104 mole of diethylaminotrimethylsilane and 0.02 mole of the Fe complex are heated to 60-65°C; reaction mixt. distd. under vac.; vinylferrocene recrystd. from hexane; products identified by chromy., IR, and mass spectrometry;	A 25% B 75%

1-ferrocenylethanol (1277-49-2) + triphenylphosphine (603-35-0) → (C5H5)Fe(C5H4CH(CH3)P(C6H5)3)(1+)*ClO4(1-) = ((C5H5)Fe(C5H4CH(CH3)P(C6H5)3))ClO4

Conditions	Yield
With perchloric acid In dichloromethane byproducts: H2O; addn. of acid to soln. of Fe-complex and phosphine in CH2Cl2 with vigorous stirring, stirring (20°C, 30 min), addn. of ether, keeping (10-15 h, 5-8°C), pptn.; filtration, washing (dry ether), crystn. (EtOH) or repptn. from soln. in acetone (ether); elem. anal.;	96%

1-ferrocenylethanol (1277-49-2) + sodium benzotriazolate (15217-42-2) → 1-N-(1-ferrocenyl-1-methyl)ethylbenzotriazole (101006-59-1, 654083-40-6, 654083-57-5)

Conditions	Yield
With tetrafluoroboric acid In dichloromethane; water byproducts: NaBF4; addn. of aq. HBF4 to mixt. of sodium benzotriazolide and Fe complex in CH2Cl2 with rapid stirring; maintaining, 1 h; evapn.; addn. of ether; washing ethereal soln. (water); drying over Na2SO4; evapn.; crystn. (hexane); elem. anal.;	96%

1-ferrocenylethanol (1277-49-2) + dimethylsulfide borane complex (13292-87-0) → 1-ethylferrocene

Conditions	Yield
In dichloromethane all manipulations under Ar atm.; to soln. of ferrocenyl compd. added equiv. amt. of soln. of B compd. in CH2Cl2, stirred at room temp. for 3.5 h; quenched with aq. NH4Cl, org. layer sepd., aq. layer extd. with CH2Cl2,combined org. extracts dried over anhyd. MgSO4, solvent removed in vac., chromy., elem. anal.;	95%

hydrogenchloride (7647-01-0) + 1-ferrocenylethanol (1277-49-2) → fc-CHCl(CH3)

Conditions	Yield
In diethyl ether in cold abs. ether;;	95%

tetrafluoroboric acid + pentetrazole (54-95-5) + 1-ferrocenylethanol (1277-49-2) → C5H5FeC5H4CHCH3N4C(CH2)5(1+)*BF4(1-)=C5H5FeC5H4CHCH3N4C(CH2)5BF4

Conditions	Yield
In dichloromethane; water aq. HBF4 was added to mixt. of corazol and Fe-complex in CH2Cl2, 15 min,Et2O was added; filtered, washed with ether, dried; elem. anal.;	94%

tetrafluoroboric acid + 1-ferrocenylethanol (1277-49-2) + 1-ferrocenylmethyl-1H-1,2,3-benzotriazole (101006-58-0) → C6N3H4((CH(CH3)C5H4)Fe(C5H5))2(1+)*BF4(1-)=C6N3H4((CH(CH3)C5H4)Fe(C5H5))2BF4 (151602-74-3)

Conditions	Yield
In dichloromethane aq. soln. of HBF4 addn. to intensively stirred soln. of Fe-compounds, stirring 3-5 min, ether addn.; ppt. filtration off, washing (water, hexane) drying (CaCl2, vacuum); elem. anal., mass spectroscopy;	94%

tetrafluoroboric acid + 1-ferrocenylethanol (1277-49-2) + hexamethylenetetramine (100-97-0) → 1,1'-bis[α-(N-hexamethylenetetramino)ethyl]ferrocene bistetrafluoroborate

Conditions	Yield
In dichloromethane aq. HBF4 addn. to vigorously stirred soln. of Fe-compounds, 4 min; ppt. filtration off, washing (cold water, pentane), drying (CaCl2, vacuum); elem. anal., mass spectroscopy;	94%

1-ferrocenylethanol (1277-49-2) + N-Phenyl-2-naphthylamine (135-88-6) → C5H5FeC5H4CH(CH3)N(C6H5)(C10H7) (93122-45-3)

Conditions	Yield
With HClO4 or HBF4 In dichloromethane byproducts: H2O; aq. HClO4 (70 %) or HBF4 (45 %) added (vigorous stirring) to the Fe-complex and the amine; soln. stirred (30 min, room temp.), addn. of ether; ether soln. washed twice (water), dried (sodium sulfate), solvent removed (vac.); elem. anal.;	93%

tetrafluoroboric acid + (η-cyclopentadienyl)(η-pyrrolyl)iron + 1-ferrocenylethanol (1277-49-2) → N-(α-ferrocenylethyl)azoniaferrocene tetrafluoroborate (170468-07-2)

Conditions	Yield
In dichloromethane aq. HBF4 addn. to vigorously stirred soln. of Fe-compounds, 5 min, diethyl ether addn., water addn.; pptn. on cooling (0°C), ppt. filtration off, washing (water, ether), drying (CaCl2, vacuum); elem. anal., mass spectroscopy;	93%

1-ferrocenylethanol (1277-49-2) + acetylene (74-86-2) → 1-(vinyloxy)ethylferrocene

Conditions	Yield
With potassium hydroxide semihydrate In dimethyl sulfoxide at 70℃; under 9880.66 Torr; for 0.75h; Temperature; Concentration; Reagent/catalyst; Autoclave;	93%
With potassium hydroxide In dimethyl sulfoxide at 70 - 80℃;	93%

1-ferrocenylethanol (1277-49-2) + C2H13B10S → 1-[(m-carboran-9-yl)thio]-1-ferrocenyl ethane

Conditions	Yield
With ammonium cerium (IV) nitrate In nitromethane at 20℃; Inert atmosphere;	93%

1-ferrocenylethanol (1277-49-2) + thiophenol (108-98-5) → 1-ferrocenyl-1-phenylethane

Conditions	Yield
With HBF4 or HClO4 In dichloromethane byproducts: H2O; aq. HBF4 (45 %) or HClO4 (70 %) added (vigorous stirring) to the Fe-complex and PhSH; soln. stirred (60 min, 20°C), addn. of ether; ether soln. washed twice (water), dried (sodium sulfate), solvent removed (vac.), recrystn. (ethanol);	92%

1-ferrocenylethanol (1277-49-2) + diphenylamine (122-39-4) → C5H5FeC5H4CH(CH3)N(C6H5)2 (93122-44-2)

Conditions	Yield
With HBF4 or HClO4 In dichloromethane byproducts: H2O; aq. HBF4 (45 %) or HClO4 (70 %) added (vigorous stirring) to the Fe-complex and the amine; soln. stirred (30 min, room temp.), addn. of ether; ether soln. washed twice (water), dried (sodium sulfate), solvent removed (vac.); elem. anal.;	92%

tetrafluoroboric acid + 1-ferrocenylethanol (1277-49-2) → (C5H5)Fe(C5H4CH(CH3)NC5H5)(1+)*BF4(1-) = ((C5H5)Fe(C5H4CH(CH3)NC5H5))BF4

Conditions	Yield
With pyridine In dichloromethane byproducts: H2O; addn. of acid to soln. of Fe-complex and base in CH2Cl2 with vigorous stirring, stirring (20°C, 45 min), addn. of ether, keeping (10-15 h, 5-8°C), pptn.; filtration, washing (dry ether), crystn. (EtOH) or repptn. from soln. in acetone (ether); elem. anal.;	92%

Upstream product

• 1271-55-2 acetylferrocene 
• 7732-18-5 water 
• 16853-85-3 lithium aluminium tetrahydride 
• 62-53-3 aniline 
• 917-64-6 methyl magnesium iodide 
• 12093-10-6 ferrocenecarboxaldehyde 
• 7647-01-0 hydrogenchloride 
• 191876-57-0 (C₅H₅)Fe(C₅H₄CH(CH₃)OCH₂COOCH₃) 
• 16940-66-2 sodium tetrahydroborate 
• 1271-51-8 vinyl ferrocene 
• 7782-79-8 hydrogen azide 

Downstream Products

• 1271-55-2 acetylferrocene 
• 1271-51-8 vinyl ferrocene 
• 31904-34-4 N,N-dimethyl-1-ferrocenylethylamine 
• 93122-44-2 C₅H₅FeC₅H₄CH(CH₃)N(C₆H₅)2 
• 93122-45-3 C₅H₅FeC₅H₄CH(CH₃)N(C₆H₅)(C₁₀H₇) 
• 13444-76-3 mercury iodide bromide 

Relevant academic research and scientific papers

Synthesis of ferrocenylketyl radicals by chromium(II) complexes

Chromium(II)-imino-diacetate (IDA), -ethylenediaminetetra-acetate (EDTA) and -1,3-propanediamine-N,N′-diacetic-N,N′-dipropionate (PDADP) complexes were used as reagents in H2O-DMF solutions at 5pH7 for the preparation of ferrocenylketyl radic

An anodic method for covalent attachment of molecules to electrodes through an ethynyl linkage

Electroactive organometallic molecules have been covalently attached to electrode surfaces through an ethynyl linkage. The process takes advantage of ethynyl-based radicals generated by anodic oxidation of a lithio-activated terminal ethynyl group. Electrophores containing redox-active ferrocene, cymantrene, or cobaltocenium moieties have been deposited at the one-to-three monolayer level. Both metal-based and ligand-based chemical reactions have been carried out on the surface-modified systems.

Kinetics of the synthesis of the S-(1-ferrocenylethyl)thioglycolic acid

A systematic study of the reactions of a number of α-hydroxylated ferrocene derivatives with thioglycolic acid confirms that the reaction is extremely fast, viz., 15-20 min , as compared with earlier procedures (12 h) .The important kinetic parame

Electrochemical Detection of Saccharides by the Redox Cycle of a Chiral Ferrocenylboronic Acid Derivative: a Novel Method for Sugar Sensing

A chiral ferrocenylboronic acid 1 bearing an intramolecular tertiary amine binds saccharides at ca. pH 7, the complexation event, which can be conveniently detected by an electrochemical method, shows chiral discrimination for certain linear saccharides.

Model solid-state reactions for the formation of a peripheral layer of organometallic dendrimers. Solid-state α-ferrocenylethylation of phenols

With the aim of modifying solid dendrite structures, the solid-state reactions of (S)-(-)-(1-trimethylammonio)ethylferrocene iodide with substituted phenols were studied.

Synthesis and structure of biologically active ferrocenylalkyl polyfluoro benzimidazoles

The title compounds were synthesized in quantitative yields by interacting α-hydroxyalkyl ferrocenes with polyfluoroalkyl benzimidazoles in an aqueous-organic medium in the presence of HBF4. The resulting diastereomers and enantiomers were reso

Enantiomeric-enriched ferrocenes: Synthesis, chiral resolution, and mathematic evaluation of CD-chiral selector energies with ferrocene-conjugates

Enantiomeric-enriched ferrocene-modified pyrazoles were synthesized via the reaction of the ferrocene alcohol, (S)-FcCH(OH)CH3 (Fc = ferrocenyl), with various pyrazoles in acidic conditions at room temperature within several minutes. X-ray structural data for racemic (R,S)-1N-(3,5-dimethyl pyrazolyl)ethyl ferrocene (1) and its (S)-enantiomer (S)-1 were determined. A series of racemic pyrazolylalkyl ferrocenes was separated into enantiomers by analytical HPLC on βand γcyclodextrins (CD) chiral stationary phases. The quantum chemical calculations of interaction energies of βCD were carried out for both (R)- and (S)-enantiomers. A high correlation between experimental HPLC data and calculated interaction energies values was obtained.

Synthesis of bis-ferrocenylpyrazoles via ferrocenylalkylation reaction

Abstract: Regioselective synthesis of bis-ferrocenylpyrazole derivatives in biphasic aquatic–organic system under catalysis with HBF4 was carried out. The regioselectivity of these reactions depending on the electronic effects of substituents i

Synthesis of 1-(1-ferrocenylethyl)-pyridinium chloride and its hybrid materials with lindquist ype polyoxometalates

A new ferrocene derivative, 1-(1-ferrocenylethyl)-pyridinium (fep = CpFeCp-CH(CH3)-Py+) chloride, and two charge ransfer salts (CTSs) based on the cationic fep donor and Lindqvist ype polyoxometalate acceptors, [fep]2[Mo6O19] (1) and [fep] 2[W6O19] (2), were synthesized. fepCl was characterized by elemental analysis, IR spectroscopy and 1H NMR and the two CTSs were characterized by elemental analysis, IR spectroscopy, UV-vis diffuse reflectance spectrum, cyclic voltammetry, fluorescence spectrum and single crystal X-ray diffraction. X-ray crystallographic studies of the brownish red CTSs 1 and 2 reveal that they are isostructural and crystallize in the monoclinic space group P21/n. In salts 1-2, fep and polyoxoanions are cocrystallized by Coulombic forces, and there also exist the complex C-H?π and π?π stacking interactions between the adjacent fep cations and C-H?O hydrogen bonds between the adjacent fep cations and polyanions. The UV-vis diffuse reflectance spectra indicate the presence of a broad charge ransfer band between 500 and 850 nm for 1-2, and CT character of 1 and 2 is also confirmed by the Mulliken correlation between the CT transition energies and the reduction potentials of the polyoxometalate acceptors. Two new hybrid materials based on 1-(1-ferrocenylethyl)-pyridinium donor and Lindqvist ype polyoxometalate acceptors were synthesized in high yields and their UV-vis diffuse reflectance spectra indicate the presence of a broad charge ransfer band between 500 and 850 nm.

Insight into the Thermal Ring-Opening Polymerization of Phospha[1]ferrocenophanes

A mixture of cis/trans isomers of phospha[1]ferrocenophanes equipped with one iPr group at the α position to the bridging PhP moiety was prepared. Both isomers (cis-4 and trans-4) were obtained as racemates and could be separated so that their thermal properties were investigated individually. The molecular structure of cis-4 was determined by single-crystal X-ray analysis showing a tilt angle α=26.35(8)°. Interconversion between both isomers occurred in the melt at elevated temperatures and revealed that the trans isomer is thermodynamically more stable. Structural and thermodynamic data was complemented by DFT calculations (B3PW91/6-311+G(d,p) and B3PW91-D3(BJ)/6-311+G(d,p)). Performance of thermal ring-opening polymerization (ROP) of trans-4 at 230 °C gave polymers and cyclic oligomers. Gel permeation chromatography (GPC) of the sulfurized polymer resulted in a molecular weight of 62.5 kDa (Mw) and a polydispersity index of 1.39 (PDI). Mass spectrometric analysis of the oligomers showed the presence of cyclic species from dimers to heptamers. After sulfurization, preparative thin layer chromatography led to the separation of three isomeric dimers. Structural characterization of these dimers by single-crystal X-ray analysis led to the conclusion that the Fe?Cp bond breaks during the thermal ROP process. A mechanism similar to the known mechanism of the photolytic ROP of ferrocenophanes is proposed.