1,1'-Diacetylferrocene

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CAS:1273-94-5
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CAS:1273-94-5
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Products Intro: Product Name:1,1'-Diacetylferrocene
CAS:1273-94-5

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  • CAS:1273-94-5
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1,1'-Diacetylferrocene Basic information
Product Name:1,1'-Diacetylferrocene
Synonyms:Ferrocene, 1,1'-diacetyl-;BIS(ACETYLCYCLOPENTADIENYL)IRON;1,1'-Diacetylferrocene ,97%;Diacetylferrocene;1,1-Diacetylferrocne;1,1'-Diacetylferrocene,98%;1,1′-Diacetylferrocene 97%;1,1'-Diacetylferrocene >
CAS:1273-94-5
MF:C14H14FeO210*
MW:270.1
EINECS:
Product Categories:Other Metal;Industrial/Fine Chemicals;Miscellaneous
Mol File:1273-94-5.mol
1,1'-Diacetylferrocene Structure
1,1'-Diacetylferrocene Chemical Properties
Melting point 125-127 °C(lit.)
storage temp. Inert atmosphere,Room Temperature
form solid
AppearanceBrown to reddish brown Solid
Water Solubility Insoluble
InChIInChI=1S/2C7H7O.Fe/c2*1-6(8)7-4-2-3-5-7;/h2*2-5H,1H3;
InChIKeyJNBIZDIDVCJECQ-UHFFFAOYSA-N
SMILES[C]1([CH][CH][CH][CH]1)C(=O)C.[C]1([CH][CH][CH][CH]1)C(=O)C.[Fe] |^1:0,1,2,3,4,8,9,10,11,12|
CAS DataBase Reference1273-94-5(CAS DataBase Reference)
NIST Chemistry Reference1,1'-Diacetylferrocene(1273-94-5)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22
Safety Statements 36
WGK Germany 3
RTECS LK0725666
HS Code 29319090
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Toxicitymammal (species unspecified),LDLo,intratracheal,50mg/kg (50mg/kg),BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLDBEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)KIDNEY, URETER, AND BLADDER: INCONTINENCE,"Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 62, 1999.
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
1,1'-Diacetylferrocene Usage And Synthesis
Chemical Propertiesdark orange to dark red powder
Uses1,1′-Diacetylferrocene is an organic compound used as a catalyst or ligand in certain cross-coupling reactions.
reaction suitabilitycore: iron
reagent type: catalyst
Synthesis
Ferrocene

102-54-5

Acetyl chloride

75-36-5

1,1'-Diacetylferrocene

1273-94-5

1) In a dry reaction vessel, anhydrous aluminum trichloride (0.1-0.18 moles) and methylene chloride (30-60 ml) were added and stirred until homogeneous. Subsequently, a mixed solution consisting of ferrocene (0.03-0.06 moles), methylene chloride (80-100 ml) and acetyl chloride (0.1-0.16 moles) was added slowly and dropwise. The reaction was first stirred at room temperature for 3-5 hours and then heated to reflux for 3-4 hours. Upon completion of the reaction, 70-100 ml of distilled water was slowly added to hydrolyze the aluminum trichloride, taking care to prevent splashing. After completion of hydrolysis, the reaction mixture was extracted with dichloromethane and the lower organic phase was separated in a separatory funnel. The upper aqueous phase was extracted three times with a small amount of dichloromethane and the organic phases were combined. The organic phase was dried with anhydrous magnesium sulfate, filtered to remove the desiccant and concentrated to give the crude product. The crude product was purified by aqueous recrystallization to give red needle-like crystals of 1,1'-diacetylferrocene in about 80% yield.

References[1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 10, p. 1551 - 1557
[2] Patent: CN108530493, 2018, A. Location in patent: Paragraph 0032; 0038; 0044; 0049
[3] Patent: CN107226829, 2017, A. Location in patent: Paragraph 0022; 0026; 0030
[4] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9563 - 9569
[5] Patent: CN104292274, 2017, B. Location in patent: Paragraph 0057
1,1'-Diacetylferrocene Preparation Products And Raw materials
Raw materialsAluminum chloride-->Acetyl chloride-->Ferrocene-->Dichloromethane
Preparation Products1,1'-DIETHYLFERROCENE
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