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361003

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

Signal Word

Danger

Hazard Statements

H290,H318

Hazard Classifications

Eye Dam. 1 - Met. Corr. 1

Storage Class Code

8B - Non-combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBB0033V
SHBB0033
04396JJ
22421CR
14921BA

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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)
Reaction in dry media: silica gel supported ferric chloride catalyzed synthesis of 1,8-dioxo-octahydroxanthene derivatives.
Shaterian HR, et al.
Phosphorus, Sulfur, and Silicon and the Related Elements, 183(12), 3136-3144 (2008)
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)
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)
Anhydrous ferric chloride adsorbed on silica gel induced ring enlargement of tertiary cyclobutanols: Synthesis of isolaurolene and derivatives, campholenic ether and (?) cuparene.
Fadel A and Salaun J.
Tetrahedron, 41(2), 413-420 (1985)
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