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Cas Database |
| Name |
Ferrocenecarboxaldehyde |
EINECS | 235-158-1 |
| CAS No. | 12093-10-6 | Density | 1.149g/cm3 |
| PSA | 17.07000 | LogP | 1.60960 |
| Solubility | insoluble | Melting Point |
118-120 °C(lit.) |
| Formula | C11H10FeO | Boiling Point | 213.6 °C at 760 mmHg |
| Molecular Weight | 214.047 | Flash Point | 98.8 °C |
| Transport Information | N/A | Appearance | crystalline solid |
| Safety | 22-24/25 | Risk Codes | R45; R23/24/25; R34; R42/43 |
| Molecular Structure |
|
Hazard Symbols |
 T
|
| 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; |
Article Data | 148 |
Ferrocenecarboxaldehyde Synthetic route
| Conditions | Yield |
|---|---|
| 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% |
- 12093-10-6
ferrocenecarboxaldehyde
| Conditions | Yield |
|---|---|
| With sodium hydride; sodium iodide In tetrahydrofuran at 40℃; chemoselective reaction; | 94% |
- 1273-86-5
1-ferrocenylmethanol
- 12093-10-6
ferrocenecarboxaldehyde
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| In diethyl ether Ar; pptn. on mixing; filtration, evapn. of soln.; | A 90% B n/a |
| Conditions | Yield |
|---|---|
| In diethyl ether Ar; pptn. on mixing; filtration, evapn. of soln.; | A 90% B n/a |
- 12093-10-6
ferrocenecarboxaldehyde
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| With trichlorophosphate for 72h; | 73% |
| Conditions | Yield |
|---|---|
| In dichloromethane presence of AlCl3, Cl2CHOC2H5 excess, 0°C;; | 72% |
Ferrocenecarboxaldehyde Chemical Properties
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
Ferrocenecarboxaldehyde Safety Profile
Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
Ferrocenecarboxaldehyde 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.
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