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710857

Sigma-Aldrich

Iron(III) chloride solution

greener alternative

0.2 M in 2-methyltetrahydrofuran

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:
12161600
PubChem Substance ID:
329763016
NACRES:
NA.22

form

solution

Quality Level

100

reaction suitability

core: iron
reagent type: catalyst

greener alternative product characteristics

Safer Solvents and Auxiliaries
Use of Renewable Feedstocks
Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

concentration

0.2 M in 2-methyltetrahydrofuran

refractive index

n20/D 1.414

density

0.868 g/mL at 25 °C

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

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. FeCl3 is used in many biomass conversion processes because of its unique properties such as nontoxicity, low-cost, abundance, and high selectivity. Here, this product is 0.2 M in 2-methyltetrahydrofuran and thus aligns with "Safer Solvents and Auxiliaries", "Use of Renewable Feedstocks", and has been enhanced for catalytic efficiency. Click here for more information.

Application

Iron(III) chloride in greener solvent, 2-methyltetrahydrofuran (2-MeTHF) can be used:
  • As a mild oxidant for phenolic coupling reaction.
  • In dimerizing aryllithiumsand ketone enolates.
  • As a mild Lewis acid catalyst to catalyzes ene reactions.
  • In Nazarov cyclizations, Michael additions, and acetonation reactions.


2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry

Signal Word

Danger

Hazard Statements

H225,H290,H302,H315,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Met. Corr. 1 - Skin Irrit. 2

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

14.0 °F - closed cup

Flash Point(C)

-10.0 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Chen-Yu Chen et al.
Clinica chimica acta; international journal of clinical chemistry, 438, 337-341 (2014-10-05)
Insulin-like growth factor binding protein-1 (IGFBP-1) constitutes a subgroup of the insulin-like growth factor binding protein systems, and its concentration in amniotic fluid is 100-1000 times higher than the concentration in other body fluids. The aim of this study was
D C Florian Wieland et al.
Colloids and surfaces. B, Biointerfaces, 109, 74-81 (2013-04-27)
The early stages of the formation of inorganic aggregates, composed of iron compounds at the solution-air interface, were investigated in situ. The properties of the solution-air interface were changed by using different Langmuir layers. In order to get insight into
Dattatraya H Dethe et al.
Organic letters, 15(3), 429-431 (2013-01-16)
A novel approach was developed for the synthesis of highly substituted indene derivatives, using an FeCl(3) catalyzed Prins-type cyclization reaction which was further applied in the total synthesis of jungianol and epi-jungianol.
Rodolphe Beaud et al.
Angewandte Chemie (International ed. in English), 51(50), 12546-12550 (2012-11-06)
IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl(3) features a rare example of the electrophilic reactivity of the indole core in a Friedel-Crafts reaction. This indole umpolung allows us straightforward access to the
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