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12093-10-6

Basic Information
CAS No.: 12093-10-6
Name: Ferrocenecarboxaldehyde
Article Data: 148
Molecular Structure:
Molecular Structure of 12093-10-6 (Ferrocenecarboxaldehyde)
Formula: C11H10FeO
Molecular Weight: 214.047
Synonyms: Ferrocenecarboxaldehyde(8CI);Iron, cyclopentadienyl(formylcyclopentadienyl)- (6CI,7CI);1-Formylferrocene;2-Ferrocenecarboxaldehyde;Cyclopentadienecarboxaldehyde,cyclopentadienyliron deriv.;Ferrocene-1-carboxaldehyde;Ferrocenecarbaldehyde;Ferrocenylcarbaldehyde;Ferrocene, formyl-;Formyldicyclopentadienyliron;Formylferrocene;NSC 407052;
EINECS: 235-158-1
Density: 1.149g/cm3
Melting Point: 118-120 °C(lit.)
Boiling Point: 213.6 °C at 760 mmHg
Flash Point: 98.8 °C
Solubility: insoluble
Appearance: crystalline solid
Hazard Symbols: T
Risk Codes: R45; R23/24/25; R34; R42/43
Safety: 22-24/25
PSA: 17.07000
LogP: 1.60960
Synthetic route
102-54-5

ferrocene

93-61-8

N-methyl-N-phenylformamide

12093-10-6

ferrocenecarboxaldehyde

Conditions
ConditionsYield
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%

N,N-dimethylferrocene carboxamide

12093-10-6

ferrocenecarboxaldehyde

Conditions
ConditionsYield
With sodium hydride; sodium iodide In tetrahydrofuran at 40℃; chemoselective reaction;94%
1273-86-5

1-ferrocenylmethanol

12093-10-6

ferrocenecarboxaldehyde

Conditions
ConditionsYield
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%
102-54-5

ferrocene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

12093-10-6

ferrocenecarboxaldehyde

B

1271-48-3

1,1'-ferrocenyldicarboxaldehyde

Conditions
ConditionsYield
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%
102-54-5

ferrocene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

12093-10-6

ferrocenecarboxaldehyde

Conditions
ConditionsYield
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%
1293-79-4

ferrocenoyl chloride

Cp2NbH(CO)

A

12093-10-6

ferrocenecarboxaldehyde

B

Nb(η-C5H5)2Cl(CO)

Conditions
ConditionsYield
In diethyl ether Ar; pptn. on mixing; filtration, evapn. of soln.;A 90%
B n/a
1293-79-4

ferrocenoyl chloride

Cp2Ta(CO)H

A

12093-10-6

ferrocenecarboxaldehyde

B

(η5-C5H5)2Ta(CO)Cl

Conditions
ConditionsYield
In diethyl ether Ar; pptn. on mixing; filtration, evapn. of soln.;A 90%
B n/a

C17H16FeN2O

12093-10-6

ferrocenecarboxaldehyde

Conditions
ConditionsYield
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%
N-Methylformamide

N-Methylformamide

102-54-5

ferrocene

12093-10-6

ferrocenecarboxaldehyde

Conditions
ConditionsYield
With trichlorophosphate for 72h;73%
102-54-5

ferrocene

5374-05-0

(dichloromethoxy)ethane

12093-10-6

ferrocenecarboxaldehyde

Conditions
ConditionsYield
In dichloromethane presence of AlCl3, Cl2CHOC2H5 excess, 0°C;;72%
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    Product Name: Ferrocenecarboxaldehyde CAS: 12093-10-6 MF: C11H10FeO10* MW: 214.04 EINECS: 235-158-1 Mol File: 12093-10-6.mol Ferrocenecarboxaldehyde Structure Ferrocenecarboxaldehyde Chemical Properties Melting point 118-120 &

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    12093-10-6 CAS NO.12093-10-6

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    Melting point 118-120 °C(lit.) Water Solubility INSOLUBLE Stability: Stable. Incompatible with strong oxidizing agents. EPA Substance Registry System Ferrocene, formyl-(12093-10-6) Safety Information Safety Statements 22-24/25 WG

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Chemistry

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 Profile

Safety Statements: 22-24/25 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3

Specification

 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.