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Sigma-Aldrich

Iron(III) chloride on silica gel

powder, extent of labeling: 5 wt. % loading

Synonym(s):

Ferric chloride on silica gel

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About This Item

Empirical Formula (Hill Notation):
Cl3Fe
CAS Number:
7705-08-0
Molecular Weight:
162.20
MDL number:
MFCD00011005
UNSPSC Code:
12352300
PubChem Substance ID:
57649442
NACRES:
NA.21

form

powder

concentration

4-6 wt. % (FeCl3 basis, Na2S2O3, titration)

extent of labeling

5 wt. % loading

impurities

1.00-10.00% water (Karl Fischer)

SMILES string

Cl[Fe](Cl)Cl

InChI

1S/3ClH.Fe/h3*1H;/q;;;+3/p-3

InChI key

RBTARNINKXHZNM-UHFFFAOYSA-K

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General description

Iron(III) chloride on silica gel consists of ferric chloride adsorbed on silica gel. It is a lewis acid commonly used in various chemical reactions like dehydration, acetal cleavage, rearrangements, thioacetalization and oxidative cyclizations. One of the methods reported for its synthesis is adding silica gel to an acetone solution followed by evaporating the solvent and then heating the mixture.

Application

Iron(III) chloride on silica gel may be used as heterogeneous catalyst in the following studies:
  • Efficient and selective cleavage of acetals and ketals.
  • Synthesis of 4(3H)-quinazolinones under solvent free conditions.
  • Rapid, high yield and selective dehydration of alcohols.
  • To induce ring enlargement of tertiary cyclobutanols.
  • Synthesis of 5-substituted 1H-tetrazole derivatives and1,8-dioxo-octahydroxanthene derivatives.
  • Protection of 1,5-dihydro-2,4-benzodithiepines.
  • Thioacetalization of carbonyl compounds.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H290,H318

Hazard Classifications

Eye Dam. 1 - Met. Corr. 1

Storage Class

8B - Non-combustible corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

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Reactions in dry media. Ferric chloride adsorbed on silica gel. A multipurpose, easily controllable reagent.
Keinan E and Mazur Y.
The Journal of Organic Chemistry, 43(5), 1020-1022 (1978)
A Mild and Efficient Method for the Protection of Carbonyl Compounds as 1, 5-Dihydro-2, 4-benzodithiepines Using Anhydrous Iron (III) Chloride Dispersed on Silica Gel.
Patney HK.
Synthetic Communications, 23(13), 1829-1833 (1993)
Silica gel/FeCl3: An efficient and recyclable heterogenous catalyst for one step synthesis of 4(3H)-quinazolinones under solvent free conditions.
Chari MA, et al.
Catalysis Communications, 7(10), 787-790 (2006)
Efficient and selective cleavage of acetals and ketals using ferric chloride adsorbed on silica gel.
Kim KS, et al.
The Journal of Organic Chemistry, 51(3), 404-407 (1986)
A rapid mild and efficient method of thioacetalization using anhydrous iron (III) chloride dispersed on silica gel.
Patney HK.
Tetrahedron Letters, 32(20), 2259-2260 (1991)
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