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1277-49-2

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1277-49-2 Usage

Chemical Properties

yellow to yellow-orange crystalline powder

Uses

Different sources of media describe the Uses of 1277-49-2 differently. You can refer to the following data:
1. Ligand in titanium-catalyzed intermolecular hydroamination of terminal alkynes (Markovnikov vs. anti-Markovnikov addition) . Reactant for: Single-electron transfer living radical polymerization reactions. Preparation of ferrocene-modified thiopyrimidines as anticancer agents. Preparation of rersible addition-fragmentation chain transfer (RAFT) agent for RAFT polymerization of styrene.
2. Ligand in titanium-catalyzed intermolecular hydroamination of terminal alkynes (Markovnikov vs. anti-Markovnikov addition)Reactant for:Single-electron transfer living radical polymerization reactionsPreparation of ferrocene-modified thiopyrimidines as anticancer agentsPreparation of rersible addition-fragmentation chain transfer (RAFT) agent for RAFT polymerization of styrene

Check Digit Verification of cas no

The CAS Registry Mumber 1277-49-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,7 and 7 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1277-49:
(6*1)+(5*2)+(4*7)+(3*7)+(2*4)+(1*9)=82
82 % 10 = 2
So 1277-49-2 is a valid CAS Registry Number.

1277-49-2 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (L19681)  (±)-1-Ferrocenylethanol, 99%   

  • 1277-49-2

  • 1g

  • 187.0CNY

  • Detail
  • Alfa Aesar

  • (L19681)  (±)-1-Ferrocenylethanol, 99%   

  • 1277-49-2

  • 5g

  • 772.0CNY

  • Detail
  • Aldrich

  • (369268)  α-Methylferrocenemethanol  97%

  • 1277-49-2

  • 369268-1G

  • 265.59CNY

  • Detail

1277-49-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(Ferrocenyl)ethanol

1.2 Other means of identification

Product number -
Other names Oacute

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1277-49-2 SDS

1277-49-2Synthetic route

acetylferrocene
1271-55-2

acetylferrocene

1-ferrocenylethanol
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%
ferrocenecarboxaldehyde
12093-10-6

ferrocenecarboxaldehyde

1-ferrocenylethanol
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%
acetylferrocene
1271-55-2

acetylferrocene

water
7732-18-5

water

1-ferrocenylethanol
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%
ferrocenecarboxaldehyde
12093-10-6

ferrocenecarboxaldehyde

A

vinyl ferrocene
1271-51-8

vinyl ferrocene

B

1-ferrocenylethanol
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%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

ferrocenecarboxaldehyde
12093-10-6

ferrocenecarboxaldehyde

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
In diethyl ether reflux;85.3%
lithium borohydride

lithium borohydride

acetylferrocene
1271-55-2

acetylferrocene

A

vinyl ferrocene
1271-51-8

vinyl ferrocene

B

1-ferrocenylethanol
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%
vinyl ferrocene
1271-51-8

vinyl ferrocene

A

1-ethylferrocene

1-ethylferrocene

B

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

C

butane-2,3-diyldiferrocene

butane-2,3-diyldiferrocene

D

C5H5FeC5H4CH(CH3)OC2H5

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
acetylferrocene
1271-55-2

acetylferrocene

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

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

1-ferrocenylethanol
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

1-methoxyethyl ferrocene

A

acetylferrocene
1271-55-2

acetylferrocene

B

vinyl ferrocene
1271-51-8

vinyl ferrocene

C

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

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

lithium aluminium tetrahydride

acetylferrocene
1271-55-2

acetylferrocene

A

vinyl ferrocene
1271-51-8

vinyl ferrocene

B

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
In tetrahydrofuran room temp., 16 h;
S-(1-ferrocenylethyl)thioglycolic acid

S-(1-ferrocenylethyl)thioglycolic acid

aniline
62-53-3

aniline

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

hydrogenchloride
7647-01-0

hydrogenchloride

(C5H5)Fe(C5H4CH(CH3)OCH2COOCH3)
191876-57-0

(C5H5)Fe(C5H4CH(CH3)OCH2COOCH3)

A

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

B

α,α'-diferrocenyldiethyl ether

α,α'-diferrocenyldiethyl ether

Conditions
ConditionsYield
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

sodium tetrahydroborate

acetylferrocene
1271-55-2

acetylferrocene

A

vinyl ferrocene
1271-51-8

vinyl ferrocene

B

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
In methanol room temp., 16 h;
(C5H5)Fe(C5H4CH(CH3)N(CH3)3)(1+)*I(1-)=[(C5H5)Fe(C5H4CH(CH3)N(CH3)3)]I

(C5H5)Fe(C5H4CH(CH3)N(CH3)3)(1+)*I(1-)=[(C5H5)Fe(C5H4CH(CH3)N(CH3)3)]I

A

vinyl ferrocene
1271-51-8

vinyl ferrocene

B

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
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

hydrogen azide

vinyl ferrocene
1271-51-8

vinyl ferrocene

A

acetylferrocene
1271-55-2

acetylferrocene

B

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

C

1-ferrocenylethyl acetate

1-ferrocenylethyl acetate

D

1-azido-ethylferrocene

1-azido-ethylferrocene

Conditions
ConditionsYield
With acetic acid In benzene
With CH3COOH In benzene
fc-CHCl(CH3)

fc-CHCl(CH3)

A

acetylferrocene
1271-55-2

acetylferrocene

B

vinyl ferrocene
1271-51-8

vinyl ferrocene

C

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
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)

fc-CHCl(CH3)

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
With water; sodium carbonate In water -78°C;;
{C5H5FeC5H4CHCH3}(1+)*BF4(1-)={C5H5FeC5H4CHCH3}BF4

{C5H5FeC5H4CHCH3}(1+)*BF4(1-)={C5H5FeC5H4CHCH3}BF4

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
With hydroxide In water alkaline hydrolysis;;
With OH(1-) In water alkaline hydrolysis;;
C5H5FeC5H4C(CH3)N2

C5H5FeC5H4C(CH3)N2

A

acetylferrocene
1271-55-2

acetylferrocene

B

vinyl ferrocene
1271-51-8

vinyl ferrocene

C

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

D

1,2-diferrocenyl-1-methyl cyclopropane

1,2-diferrocenyl-1-methyl cyclopropane

E

(C10H9FeCH(CH3)N)2

(C10H9FeCH(CH3)N)2

Conditions
ConditionsYield
In benzene
In benzene
In benzene
(C5H5)Fe(C5H4CH(CH3)N(CH3)3)(1+)*I(1-)=[(C5H5)Fe(C5H4CH(CH3)N(CH3)3)]I

(C5H5)Fe(C5H4CH(CH3)N(CH3)3)(1+)*I(1-)=[(C5H5)Fe(C5H4CH(CH3)N(CH3)3)]I

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
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

sodium dicarbonyl(cyclopentadienyl)ferrate

fc-CO-CH2-Fe(CO)2C5H5

fc-CO-CH2-Fe(CO)2C5H5

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2;
byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2;
fc-CO-CH2-Fe(CO)2C5H5

fc-CO-CH2-Fe(CO)2C5H5

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2;
With LiAlH4 byproducts: C10H9FeCOCH3, (C5H5Fe(CO)2)2;
C10H9FeCH(CH3)OSO2F

C10H9FeCH(CH3)OSO2F

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
With water
(+)-(R)-C10H9FeCH(CH3)-S-CS-S-CH3

(+)-(R)-C10H9FeCH(CH3)-S-CS-S-CH3

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
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

fc-CHCH3-Zr(C5H5)2Cl

A

(μ-oxo)bis[chlorobis(cyclopentadienyl)zirconium(IV)]

(μ-oxo)bis[chlorobis(cyclopentadienyl)zirconium(IV)]

B

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
With water In diethyl ether; water
With H2O In diethyl ether; water
ferrocenylmethyl acetate

ferrocenylmethyl acetate

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
With methanol In methanol Kinetics; methanolysis at 0°C; IR;
4-(1-ferrocenylethoxy)-3-methoxybenzaldehyde

4-(1-ferrocenylethoxy)-3-methoxybenzaldehyde

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
With water In acetone byproducts: vanillin; heating in aq. acetone;>99
4-(1-ferrocenylethoxy)benzaldehyde

4-(1-ferrocenylethoxy)benzaldehyde

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
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

(C6H5)CN4H(CH(CH3)(C5H4)Fe(C5H5))(1+)*BF4(1-)=[C6H5CN4H(CH(CH3)(C5H4)Fe(C5H5))]BF4

A

5-Phenyl-1H-tetrazole
18039-42-4

5-Phenyl-1H-tetrazole

B

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

Conditions
ConditionsYield
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

1-ferrocenylethanol

α-hydroxyethylferrocene*γ-cyclodextrin

α-hydroxyethylferrocene*γ-cyclodextrin

Conditions
ConditionsYield
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

1-ferrocenylethanol

β-cyclodextrin decahydrate

β-cyclodextrin decahydrate

α-hydroxyethylferrocene*β-cyclodextrin*2H2O

α-hydroxyethylferrocene*β-cyclodextrin*2H2O

Conditions
ConditionsYield
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

1-ferrocenylethanol

mercaptoacetic acid
68-11-1

mercaptoacetic acid

S-(1-ferrocenylethyl)thioglycolic acid

S-(1-ferrocenylethyl)thioglycolic acid

Conditions
ConditionsYield
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

1-ferrocenylethanol

water
7732-18-5

water

1-ethylferrocene

1-ethylferrocene

Conditions
ConditionsYield
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

1-ferrocenylethanol

acetic anhydride
108-24-7

acetic anhydride

1-ferrocenylethyl acetate

1-ferrocenylethyl acetate

Conditions
ConditionsYield
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

1-ferrocenylethanol

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

aniline
62-53-3

aniline

A

1-[N-phenylamino]ethylferrocene

1-[N-phenylamino]ethylferrocene

B

C5H5FeC5H4CH(CH3)OC2H5

C5H5FeC5H4CH(CH3)OC2H5

Conditions
ConditionsYield
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

1-ferrocenylethanol

vinyl ferrocene
1271-51-8

vinyl ferrocene

Conditions
ConditionsYield
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

1,2,3-Benzotriazole

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

1-N-(1-ferrocenyl-1-methyl)ethylbenzotriazole
101006-59-1, 654083-40-6, 654083-57-5

1-N-(1-ferrocenyl-1-methyl)ethylbenzotriazole

Conditions
ConditionsYield
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

1-ferrocenylethanol

N,N-Dimethyltrimethylsilylamine
2083-91-2

N,N-Dimethyltrimethylsilylamine

trimethyl(α-ferrocenylethoxy)silane

trimethyl(α-ferrocenylethoxy)silane

Conditions
ConditionsYield
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

1-ferrocenylethanol

N,N-diethyl-1,1,1-trimethylsilanamine
996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

trimethyl(α-ferrocenylethoxy)silane

trimethyl(α-ferrocenylethoxy)silane

Conditions
ConditionsYield
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

1-ferrocenylethanol

thiophenol
108-98-5

thiophenol

(1-ferrocenylethyl) phenyl sulfide

(1-ferrocenylethyl) phenyl sulfide

Conditions
ConditionsYield
With CF3COOH or CH3COOH96%
With tetrafluoroboric acid In dichloromethane; water at 20℃; for 0.0833333h;83%
1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

N,N-diethyl-1,1,1-trimethylsilanamine
996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

A

vinyl ferrocene
1271-51-8

vinyl ferrocene

B

trimethyl(α-ferrocenylethoxy)silane

trimethyl(α-ferrocenylethoxy)silane

Conditions
ConditionsYield
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

1-ferrocenylethanol

triphenylphosphine
603-35-0

triphenylphosphine

(C5H5)Fe(C5H4CH(CH3)P(C6H5)3)(1+)*ClO4(1-) = ((C5H5)Fe(C5H4CH(CH3)P(C6H5)3))ClO4

(C5H5)Fe(C5H4CH(CH3)P(C6H5)3)(1+)*ClO4(1-) = ((C5H5)Fe(C5H4CH(CH3)P(C6H5)3))ClO4

Conditions
ConditionsYield
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

1-ferrocenylethanol

sodium benzotriazolate
15217-42-2

sodium benzotriazolate

1-N-(1-ferrocenyl-1-methyl)ethylbenzotriazole
101006-59-1, 654083-40-6, 654083-57-5

1-N-(1-ferrocenyl-1-methyl)ethylbenzotriazole

Conditions
ConditionsYield
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

1-ferrocenylethanol

dimethylsulfide borane complex
13292-87-0

dimethylsulfide borane complex

1-ethylferrocene

1-ethylferrocene

Conditions
ConditionsYield
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

hydrogenchloride

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

fc-CHCl(CH3)

fc-CHCl(CH3)

Conditions
ConditionsYield
In diethyl ether in cold abs. ether;;95%
tetrafluoroboric acid

tetrafluoroboric acid

pentetrazole
54-95-5

pentetrazole

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

C5H5FeC5H4CHCH3N4C(CH2)5(1+)*BF4(1-)=C5H5FeC5H4CHCH3N4C(CH2)5BF4

C5H5FeC5H4CHCH3N4C(CH2)5(1+)*BF4(1-)=C5H5FeC5H4CHCH3N4C(CH2)5BF4

Conditions
ConditionsYield
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

tetrafluoroboric acid

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

1-ferrocenylmethyl-1H-1,2,3-benzotriazole
101006-58-0

1-ferrocenylmethyl-1H-1,2,3-benzotriazole

C6N3H4((CH(CH3)C5H4)Fe(C5H5))2(1+)*BF4(1-)=C6N3H4((CH(CH3)C5H4)Fe(C5H5))2BF4
151602-74-3

C6N3H4((CH(CH3)C5H4)Fe(C5H5))2(1+)*BF4(1-)=C6N3H4((CH(CH3)C5H4)Fe(C5H5))2BF4

Conditions
ConditionsYield
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

tetrafluoroboric acid

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

hexamethylenetetramine
100-97-0

hexamethylenetetramine

1,1'-bis[α-(N-hexamethylenetetramino)ethyl]ferrocene bistetrafluoroborate

1,1'-bis[α-(N-hexamethylenetetramino)ethyl]ferrocene bistetrafluoroborate

Conditions
ConditionsYield
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

1-ferrocenylethanol

N-Phenyl-2-naphthylamine
135-88-6

N-Phenyl-2-naphthylamine

C5H5FeC5H4CH(CH3)N(C6H5)(C10H7)
93122-45-3

C5H5FeC5H4CH(CH3)N(C6H5)(C10H7)

Conditions
ConditionsYield
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

tetrafluoroboric acid

(η-cyclopentadienyl)(η-pyrrolyl)iron

(η-cyclopentadienyl)(η-pyrrolyl)iron

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

N-(α-ferrocenylethyl)azoniaferrocene tetrafluoroborate
170468-07-2

N-(α-ferrocenylethyl)azoniaferrocene tetrafluoroborate

Conditions
ConditionsYield
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

1-ferrocenylethanol

acetylene
74-86-2

acetylene

1-(vinyloxy)ethylferrocene

1-(vinyloxy)ethylferrocene

Conditions
ConditionsYield
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

1-ferrocenylethanol

C2H13B10S

C2H13B10S

1-[(m-carboran-9-yl)thio]-1-ferrocenyl ethane

1-[(m-carboran-9-yl)thio]-1-ferrocenyl ethane

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate In nitromethane at 20℃; Inert atmosphere;93%
1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

thiophenol
108-98-5

thiophenol

1-ferrocenyl-1-phenylethane

1-ferrocenyl-1-phenylethane

Conditions
ConditionsYield
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

1-ferrocenylethanol

diphenylamine
122-39-4

diphenylamine

C5H5FeC5H4CH(CH3)N(C6H5)2
93122-44-2

C5H5FeC5H4CH(CH3)N(C6H5)2

Conditions
ConditionsYield
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

tetrafluoroboric acid

1-ferrocenylethanol
1277-49-2

1-ferrocenylethanol

(C5H5)Fe(C5H4CH(CH3)NC5H5)(1+)*BF4(1-) = ((C5H5)Fe(C5H4CH(CH3)NC5H5))BF4

(C5H5)Fe(C5H4CH(CH3)NC5H5)(1+)*BF4(1-) = ((C5H5)Fe(C5H4CH(CH3)NC5H5))BF4

Conditions
ConditionsYield
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%

1277-49-2Relevant articles and documents

Synthesis of ferrocenylketyl radicals by chromium(II) complexes

Ratkovic, Zoran R.,Somsák, L.ászló,Micskei, K.ároly,Zucchi, Claudia,Pályi, Gyula

, p. 813 - 819 (2001)

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

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

Scutaru, D.,Tataru, Lucia,Mazilu, I.,Scutaru, Brigitte,Lixandru, Tatiana,Simionescu, Cr.

, p. 99 - 102 (1989)

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

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

Khrushcheva,Belousova,Loim,Sokolov

, p. 1106 - 1108 (2000)

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

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

Snegur, Lubov V.,Borisov, Yurii A.,Kuzmenko, Yuliya V.,Davankov, Vadim A.,Ilyin, Mikhail M.,Ilyin, Mikhail M.,Arhipov, Dmitry E.,Korlyukov, Alexander A.,Kiselev, Sergey S.,Simenel, Alexander A.

, (2017)

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

Niu, Yujuan,Ren, Xiaoyu,Yin, Bin,Wang, Danjun,Xue, Ganglin,Hu, Huaiming,Fu, Feng,Wang, Jiwu

, p. 1863 - 1868 (2010)

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.

1-D manganese(ii)-terpyridine coordination polymers as precatalysts for hydrofunctionalisation of carbonyl compounds

Johnson, Jahvon,Li, Sihan,Mo, Zixuan,Neary, Michelle C.,Zeng, Haisu,Zhang, Guoqi,Zheng, Shengping

supporting information, p. 2610 - 2615 (2020/03/05)

Reductive catalysis with earth-abundant metals is currently of increasing importance and shows potential in replacing precious metal catalysis. In this work, we revealed catalytic hydroboration and hydrosilylation of ketones and aldehydes achieved by a structurally defined manganese(ii) coordination polymer (CP) as a precatalyst under mild conditions. The manganese-catalysed methodology can be applied to a range of functionalized aldehydes and ketones with turnover numbers (TON) of up to 990. Preliminary results on the regioselective catalytic hydrofunctionalization of styrenes by the Mn-CP catalyst are also presented.

Synthesis of ferrocenyl-containing silicone rubbers via platinum-catalyzed Si–H self-cross-linking

Deriabin, Konstantin V.,Lobanovskaia, Ekaterina K.,Kirichenko, Sergey O.,Barshutina, Marie N.,Musienko, Pavel E.,Islamova, Regina M.

, (2019/11/22)

Self-cross-linkable ferrocenyl-containing polymethylhydrosiloxanes were synthesized. Karstedt's catalyst and cis-[PtCl2(BnCN)2] were examined as cross-linking catalysts at room temperature for the reaction between Si–H groups of the ferrocenyl-containing polymethylhydrosiloxanes. Cis-[PtCl2(BnCN)2] is an effective catalyst that allows cross-linked ferrocenyl-containing silicones (silicone rubbers) to be obtained with no visible mechanical defects (bubbles or cracks) compared with Karstedt's catalyst. The ferrocene content of the ferrocenyl-containing silicone rubbers was found to be approximately 50?wt.% by energy-dispersive X-ray analysis. Compared with cross-linked non-modified polymethylhydrosiloxanes, the ferrocenyl-containing silicone rubbers exhibited improved tensile properties (the tensile strength increased from 0.47 to 0.75?MPa) and a 1.5–2.5 times lower cross-linking degree. The surface resistivity of the ferrocenyl-containing silicone rubbers (50?wt.% ferrocenyl units) was approximately 7 × 109?Ω/□, which was 10,000 times lower than that of pure polymethylhydrosiloxane. The obtained flexible electroactive ferrocenyl-containing silicone rubbers can potentially be applied as coatings for electronic and electrostatic-sensitive devices, interfaces, and sensors.

Practical and selective hydroboration of aldehydes and ketones in air catalysed by an iron(ii) coordination polymer

Zhang, Guoqi,Cheng, Jessica,Davis, Kezia,Bonifacio, Mary Grace,Zajaczkowski, Cynthia

, p. 1114 - 1121 (2019/03/12)

The in air catalytic hydroboration of ketones and aldehydes with pinacolborane by an iron(ii) coordination polymer (CP) is carried out under mild and solvent-free conditions. The precatalyst is highly active towards a wide range of substrates including functionalized ketones and aldehydes in the presence of KOtBu as an activator, achieving a high turnover number (TON) of up to 9500. Excellent chemoselectivity to aldehydes over ketones was also revealed, which is in sharp contrast with the results obtained under inert atmosphere using the same catalyst system. This catalyst observed here is not only highly efficient but also recyclable for reuse for at least 5 times without losing its effectiveness.

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