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12322

Sigma-Aldrich

Iron(III) chloride solution

greener alternative

purum, 45% FeCl3 basis

Synonym(s):

Ferric chloride solution

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About This Item

Linear Formula:
FeCl3
CAS Number:
7705-08-0
Molecular Weight:
162.20
MDL number:
MFCD00011005
UNSPSC Code:
12352302
PubChem Substance ID:
329749708
NACRES:
NA.55

Quality Level

100

grade

purum

form

liquid

reaction suitability

reagent type: catalyst
core: iron

greener alternative product characteristics

Catalysis
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concentration

45% (FeCl3)

greener alternative category

, Aligned

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 is a mild oxidizing agent. It is widely employed as a Lewis acid in organic synthesis. On crystallization with water, it forms hydrates. It can be prepared by passing chlorine over scrap iron at approximately 650°C.
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Application

Iron(III) chloride may be used for the polymerization of pyrrole and for the preparation of the phenanthrene ring. It is widely employed for the following reactions:
  • polymerizations
  • oxidations
  • oxidative couplings
  • reductions
  • C−C bond formation
  • Ferrier rearrangement
  • one-pot multicomponent condensations
  • Friedel-Crafts reactions
  • cyclization′s
  • glycosidation
  • Prins-type cyclisation

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H290,H314

Hazard Classifications

Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1

Storage Class Code

8B - Non-combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Recent uses of iron (III) chloride in organic synthesis.
Diaz DD, et al.
Current Organic Chemistry, 10(4), 457-476 (2006)
Optimum reaction conditions for the polymerization of pyrrole by iron (III) chloride in aqueous solution.
Armes SP.
Synthetic Metals, 20(3), 365-371 (1987)
Kailiang Wang et al.
The Journal of organic chemistry, 74(2), 935-938 (2008-12-05)
Easily available and nontoxic FeCl(3) catalyzes intramolecular oxidative coupling for the direct construction of the phenanthrene ring using meta-chloroperbenzoic acid as sole oxidant at room temperature in excellent yields. The mechanistic investigations show that FeCl(3)-catalyzed coupling proceeds through the heterolytic
Eagleson M.
Concise Encyclopedia Chemistry, 553-553 (1994)
Abdelwareth A O Sarhan et al.
Chemical Society reviews, 38(9), 2730-2744 (2009-08-20)
In this critical review, the use of iron(III) chloride in oxidative C-C couplings of arenes and related unsaturated compounds is presented and reviewed. The approach allows highly selective dimerisations of phenol derivatives, naphthols, and heterocyclic compounds. Sequential couplings give access
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