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Basic Information
CAS No.: 1277-49-2
Name: 1-(Ferrocenyl)ethanol
Article Data: 74
Molecular Structure:
Molecular Structure of 1277-49-2 (1-(Ferrocenyl)ethanol)
Formula: C12H14FeO
Molecular Weight: 230.09
Synonyms: Ferrocenemethanol,a-methyl- (8CI);Iron,cyclopentadienyl[(1-hydroxyethyl)cyclopentadienyl]- (6CI,7CI);(a-Hydroxyethyl)ferrocene;1-Ferrocenylethanol;Ethanol, 1-ferrocenyl-;NSC 162110;alpha-Methylferrocenemethanol;
EINECS: -0
Density: 1.016g/cm3
Melting Point: 76-79 °C
Boiling Point: 184.6oC at 760mmHg
Flash Point: >100 °C
Solubility: Insoluble in water.
Appearance: yellow to yellow-orange crystalline powder
Hazard Symbols: IrritantXi, HarmfulXn
Risk Codes: 36/37/38-22
Safety: 26-36-37/39
PSA: 20.23000
LogP: 1.79150
Synthetic route
1271-55-2

acetylferrocene

1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
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%
12093-10-6

ferrocenecarboxaldehyde

1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
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%
1271-55-2

acetylferrocene

1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
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%
12093-10-6

ferrocenecarboxaldehyde

A

1271-51-8

vinyl ferrocene

B

1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
With methylmagnesium bromide In not given Wittig reaction;;A 6%
B 90%
With CH3MgBr In not given Wittig reaction;;A 6%
B 90%
917-64-6

methyl magnesium iodide

12093-10-6

ferrocenecarboxaldehyde

1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
In diethyl ether reflux;85.3%

lithium borohydride

1271-55-2

acetylferrocene

A

1271-51-8

vinyl ferrocene

B

1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
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%
1271-51-8

vinyl ferrocene

A

1-ethylferrocene

B

1277-49-2

1-ferrocenylethanol

C

butane-2,3-diyldiferrocene

D

C5H5FeC5H4CH(CH3)OC2H5

Conditions
ConditionsYield
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
1271-55-2

acetylferrocene

(2,2'-bipyridyl)(tetrahydroborato)zinc

1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
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

A

1271-55-2

acetylferrocene

B

1271-51-8

vinyl ferrocene

C

1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
With aluminum oxide In n-heptane ambient temp., neutral Al2O3;;A 6%
B 3%
C 44%
16853-85-3

lithium aluminium tetrahydride

1271-55-2

acetylferrocene

A

1271-51-8

vinyl ferrocene

B

1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
In tetrahydrofuran room temp., 16 h;
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    Product Name: 1-(Ferrocenyl)ethanol CAS: 1277-49-2 MF: C12H14FeO10* MW: 230.08 EINECS: 625-176-1 Mol File: 1277-49-2.mol 1-(Ferrocenyl)ethanol Structure 1-(Ferrocenyl)ethanol Chemical Properties Melting point 76-79 °C(lit.

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    1277-49-2 CAS NO.1277-49-2

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Specification

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,