(S)-(4-Isopropyloxazolin-2-yl)ferrocene TCI I0749

Chemical Identity

CAS No.: 162157-03-1
PubChem: CID 15184021·SID 87561248
Formula: C16H19FeNO
Molecular weight: 297.17 g/mol
Purity: >98.0%(GC)(T)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: cyclopenta-1,3-diene;(4S)-2-cyclopenta-1,3-dien-1-yl-4-propan-2-yl-4,5-dihydro-1,3-oxazole;iron(2+)
SMILES: CC(C)[C@H]1COC(=N1)C2=CC=C[CH-]2.[CH-]1C=CC=C1.[Fe+2]
InChIKey: MOTUFOCNRSDOMK-YQFADDPSSA-N

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TCI I0749 (S)-(4-Isopropyloxazolin-2-yl)ferrocene is a chiral organometallic compound that combines a ferrocene core with an oxazoline ring bearing an isopropyl substituent in the S configuration. The compound occupies a special position in asymmetric synthesis laboratories as a key precursor to the well-known family of ferrocenyl oxazoline ligands. Through ortho-lithiation directed by the oxazoline group, it can be converted into a wide range of bidentate phosphine-oxazoline ligands and other donor ligands, which are then used to control stereochemistry in transition metal-catalysed reactions with a high rate of success.

The property that makes this compound so highly valued is the ability of the oxazoline group to direct deprotonation to the ortho position of the cyclopentadienyl ring in a diastereoselective manner. This process creates planar chirality on the ferrocene in addition to the central chirality already present at the oxazoline carbon, so the resulting ligands carry two cooperating elements of chirality. The ferrocene core itself provides a robust framework that is air-stable in its neutral form and offers tunable electronic properties, while the isopropyl group supplies a balanced degree of steric hindrance.

In Indonesian laboratories, the compound is typically handled in university and institutional research groups working on asymmetric catalysis, chiral ligand design, and methodology development in organic synthesis. It is usually ordered in small research quantities and used at the bench under inert-atmosphere technique, since the directed lithiation step that follows requires strictly anhydrous conditions. Laboratories preparing publications or graduate theses on stereoselective transformations are the most common users of this material.

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Ligands 2025-12-01 · p. 4

Related TCI products

Synthesis of ferrocenyl phosphine-oxazoline ligands: the oxazoline group directs ortho-lithiation on the cyclopentadienyl ring, allowing a phosphine donor to be introduced at a defined position to give a bidentate P,N ligand.
Construction of planar-chiral building blocks: diastereoselective deprotonation at the ortho position installs planar chirality on the ferrocene backbone, giving access to scaffolds carrying two distinct chirality elements at once.
Preparation of catalyst systems for transition metal-catalysed asymmetric reactions: ligands derived from this precursor are used to control the stereochemical outcome of metal-mediated transformations with high levels of success.
Chiral ligand design and structure-activity studies: the isopropyl substituent provides a balanced steric environment that researchers can compare against other oxazoline substituents when tuning selectivity.
Methodology development in asymmetric synthesis: the robust, electronically tunable ferrocene framework serves as a reliable platform for developing and benchmarking new stereoselective synthetic procedures in research laboratories.

Brand	TCI (Tokyo Chemical Industry)
CAS number	162157-03-1
Molecular formula	—
Purity	—
Category	Chemistry > Asymmetric Synthesis > Chiral Catalysts, Chiral Ligands, Chiral Reagents
Pack sizes	available in standard TCI research-scale catalogue pack sizes; please confirm the current option when ordering
Physical form	—
Storage	keep in a cool, dry place in the tightly closed original container

Product code: I0749
Chemical name: (S)-(4-Isopropyloxazolin-2-yl)ferrocene

Store the container tightly closed in a cool, dry, well-ventilated area, away from direct sunlight, moisture, and sources of ignition. The original manufacturer packaging is the preferred container; if the material is transferred, use clean, dry, tightly sealed glass vessels and label them clearly. Because the ortho-lithiation chemistry this compound is intended for requires strictly anhydrous conditions, handling under an inert atmosphere and with dried glassware is recommended to protect both the material and the subsequent reaction. Handle in a fume hood, wear safety glasses, a laboratory coat, and chemically resistant gloves, avoid the formation and inhalation of dust, and consult the manufacturer's safety data sheet before use. Keep away from incompatible materials and dispose of residues in accordance with applicable laboratory waste procedures.

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