Cerium(III) Chloride Anhydrous

• CAS: 7790-86-5
• Catalog Number: ACM7790865-5
• Category: Main Products
• Molecular Weight: 246.47
• Molecular Formula: CeCl3
• Melting Point: 722 °C(lit.)
• Application: Incandescent gas mantles, spectrography,; preparation of cerium metal, polymerization cat-; alyst.

Case Study

Catalytic Application of Cerium(III) Chloride Anhydrous in the Synthesis of 3-Sulfenyl Indoles

Silveira, Claudio C., et al. Tetrahedron Letters 51.15 (2010): 2014-2016.

The cerium(III) chloride anhydrous was found to be an efficient catalyst in the synthesis of 3-sulfenyl indoles, which are highly significant synthetic intermediates in organic synthesis and pharmaceuticals. The article was focused on optimization of the reaction conditions as well as the substrate scope. The model reaction was performed between indole and N-(phenylthio)phthalimide in various conditions to find the best reaction conditions.
Key Results
· Optimal Conditions: The best yield of the reaction (88%) was obtained in the presence of 0.1 equiv. of anhydrous CeCl3 in DMF at 70°C.
· Solvent Effect: DMF was found to be a superior solvent than other solvents including MeCN, DCM, DMA, NMP, which provided enhanced reaction yield.
· Catalyst Form: Anhydrous CeCl3 dramatically outperformed its hydrated counterpart (CeCl3·7H2O), which yielded only 61% under identical conditions.
· Loading and Temperature: Reducing catalyst loading to 0.05 equiv still afforded good yield (79%), while elevated temperature (70-90°C) was essential for high efficiency. Room temperature reactions led to markedly reduced yields.
· The protocol was successfully extended to various N-(alkyl/arylthio)phthalimides and substituted indoles (e.g., 5-bromoindole, 6-methoxyindole), yielding corresponding 3-sulfenyl indoles in good to excellent yields (60-88%). The free N-H indoles proved suitable substrates without the need for N-protection.

Cerium(III) Chloride Anhydrous: A Highly Efficient Catalyst for Solvent-Free Anti-Markovnikov Thiol-Alkene Addition

Silveira, Claudio C., et al. Synlett 2010.05 (2010): 790-792.

This study reported the use of cerium(iii) chloride anhydrous (CeCl3) as a Lewis acid catalyst for the anti-Markovnikov addition of thiols to alkenes, a key transformation in the preparation of organosulfur compounds. The reaction exhibited excellent regioselectivity under mild conditions, and importantly, was performed without any solvent, making the process operationally simple and environmentally friendly.
Key Results
Optimization of reaction conditions for the model reaction of cyclohexene and thiophenol:
· Optimal Conditions: Best yield (quantitative as per GC) was observed using only 0.05 mmol of anhydrous CeCl3, solvent-free at room temperature, for 6 hours.
· Effect of Catalyst Form: A dramatic difference in the performance of anhydrous and hydrated CeCl3 was observed; the hydrated CeCl3·7H2O gave only 65% yield for the model reaction under otherwise identical conditions.
· Solvent-free conditions: Reaction proceeded with and without solvent, but the solvent-free conditions were chosen for simplicity and green chemistry principles.
· Scope of substrates: The reaction conditions were applied to a variety of alkenes (both cyclic and acyclic including dihydropyran) and thiols (aromatic and aliphatic), affording the anti-Markovnikov adducts in 78-97% isolated yield.
· Regioselectivity: Only the anti-Markovnikov product was detected by spectroscopic methods.

Custom Q&A

What is the molecular formula of Cerium(III) chloride?

The molecular formula of Cerium(III) chloride is CeCl3.

What is the molecular weight of Cerium(III) chloride?

The molecular weight of Cerium(III) chloride is 246.47 g/mol.

What are the synonyms of Cerium(III) chloride?

The synonyms of Cerium(III) chloride are cerium(3+);trichloride, 11098-86-5, Cerium-144 chloride, Cerium chloride [Generic], and more.

What is the IUPAC name of Cerium(III) chloride?

The IUPAC name of Cerium(III) chloride is cerium(3+);trichloride.

What is the InChI key of Cerium(III) chloride?

The InChI key of Cerium(III) chloride is VYLVYHXQOHJDJL-UHFFFAOYSA-K.

What is the canonical SMILES of Cerium(III) chloride?

The canonical SMILES of Cerium(III) chloride is [Cl-].[Cl-].[Cl-].[Ce+3].

What is the CAS number of Cerium(III) chloride?

The CAS number of Cerium(III) chloride is 7790-86-5.

What is the hydrogen bond donor count of Cerium(III) chloride?

The hydrogen bond donor count of Cerium(III) chloride is 0.

What is the hydrogen bond acceptor count of Cerium(III) chloride?

The hydrogen bond acceptor count of Cerium(III) chloride is 3.

Is Cerium(III) chloride compound canonicalized?

Yes, Cerium(III) chloride compound is canonicalized.