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
1-ferrocenylethanol
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% |
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% |
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% |
Conditions | Yield |
---|---|
In diethyl ether reflux; | 85.3% |
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% |
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 |
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% |
Conditions | Yield |
---|---|
With aluminum oxide In n-heptane ambient temp., neutral Al2O3;; | A 6% B 3% C 44% |
lithium aluminium tetrahydride
acetylferrocene
A
vinyl ferrocene
B
1-ferrocenylethanol
Conditions | Yield |
---|---|
In tetrahydrofuran room temp., 16 h; |
hydrogenchloride
(C5H5)Fe(C5H4CH(CH3)OCH2COOCH3)
A
1-ferrocenylethanol
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
acetylferrocene
A
vinyl ferrocene
B
1-ferrocenylethanol
Conditions | Yield |
---|---|
In methanol room temp., 16 h; |
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 |
Conditions | Yield |
---|---|
With acetic acid In benzene | |
With CH3COOH In benzene |
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;; |
1-ferrocenylethanol
Conditions | Yield |
---|---|
With water; sodium carbonate In water -78°C;; |
1-ferrocenylethanol
Conditions | Yield |
---|---|
With hydroxide In water alkaline hydrolysis;; | |
With OH(1-) In water alkaline hydrolysis;; |
Conditions | Yield |
---|---|
In benzene | |
In benzene | |
In benzene |
1-ferrocenylethanol
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; |
Conditions | Yield |
---|---|
byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2; | |
byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2; |
1-ferrocenylethanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2; | |
With LiAlH4 byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2; |
1-ferrocenylethanol
Conditions | Yield |
---|---|
With water |
1-ferrocenylethanol
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; |
B
1-ferrocenylethanol
Conditions | Yield |
---|---|
With water In diethyl ether; water | |
With H2O In diethyl ether; water |
1-ferrocenylethanol
Conditions | Yield |
---|---|
With methanol In methanol Kinetics; methanolysis at 0°C; IR; |
1-ferrocenylethanol
Conditions | Yield |
---|---|
With water In acetone byproducts: vanillin; heating in aq. acetone; | >99 |
1-ferrocenylethanol
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
A
5-Phenyl-1H-tetrazole
B
1-ferrocenylethanol
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
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
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% |
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 |
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% |
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; |
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 |
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
1-ferrocenylethanol
1-N-(1-ferrocenyl-1-methyl)ethylbenzotriazole
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; |
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% |
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% |
Conditions | Yield |
---|---|
With CF3COOH or CH3COOH | 96% |
With tetrafluoroboric acid In dichloromethane; water at 20℃; for 0.0833333h; | 83% |
1-ferrocenylethanol
N,N-diethyl-1,1,1-trimethylsilanamine
A
vinyl ferrocene
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% |
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
sodium benzotriazolate
1-N-(1-ferrocenyl-1-methyl)ethylbenzotriazole
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% |
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% |
Conditions | Yield |
---|---|
In diethyl ether in cold abs. ether;; | 95% |
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% |
1-ferrocenylethanol
1-ferrocenylmethyl-1H-1,2,3-benzotriazole
C6N3H4((CH(CH3)C5H4)Fe(C5H5))2(1+)*BF4(1-)=C6N3H4((CH(CH3)C5H4)Fe(C5H5))2BF4
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% |
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
N-Phenyl-2-naphthylamine
C5H5FeC5H4CH(CH3)N(C6H5)(C10H7)
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% |
1-ferrocenylethanol
N-(α-ferrocenylethyl)azoniaferrocene tetrafluoroborate
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% |
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% |
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate In nitromethane at 20℃; Inert atmosphere; | 93% |
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% |
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% |
1-ferrocenylethanol
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% |
The systematic name of 1-(Ferrocenyl)ethanol is cyclopenta-2,4-dien-1-yl-[2-(1-hydroxyethyl)cyclopenta-2,4-dien-1-yl]iron. With the CAS registry number 1277-49-2, it is also named as alpha-Methylferrocenemethanol. The product's categories are Industrial/Fine Chemicals; Classes of Metal Compounds; Fe (Iron) Compounds; Ferrocenes; Metallocenes; Transition Metal Compounds. Besides, it is yellow to yellow-orange crystalline powder, which should be stored in tightly sealed containers in a cool, dry place. And you should ensure that the workplaces have well ventilated or exhaust devices. In addition, its molecular formula is C12H14FeO and molecular weight is 230.08.
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. It is also harmful if swallowed. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
(1)SMILES: CC(C1=CC=CC1[Fe]C2C=CC=C2)O
(2)InChI: InChI=1/C7H9O.C5H5.Fe/c1-6(8)7-4-2-3-5-7;1-2-4-5-3-1;/h2-6,8H,1H3;1-5H;/rC12H14FeO/c1-9(14)11-7-4-8-12(11)13-10-5-2-3-6-10/h2-10,12,14H,1H3
(3)InChIKey: NJPGTUIMEAOISI-OFQXSSAXAS
(4)Std. InChI: InChI=1S/C7H9O.C5H5.Fe/c1-6(8)7-4-2-3-5-7;1-2-4-5-3-1;/h2-6,8H,1H3;1-5H
(5)Std. InChIKey: NJPGTUIMEAOISI-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 100mg/kg (100mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#08813, |
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