(R)-4-Phenylthiazolidine-2-thione TCI P1959

Chemical Identity

CAS No.: 110199-18-3
PubChem: CID 11521249·SID 253662074
Formula: C9H9NS2
Molecular weight: 195.3 g/mol
Purity: >98.0%(GC)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: (4R)-4-phenyl-1,3-thiazolidine-2-thione
SMILES: C1[C@H](NC(=S)S1)C2=CC=CC=C2
InChIKey: IEXSISKCCADMLK-QMMMGPOBSA-N

Rp 2.464.350,00

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(R)-4-Phenylthiazolidine-2-thione is a chiral auxiliary from the thiazolidine-2-thione family. The molecule is a five-membered ring that contains sulfur and nitrogen. It carries a thiocarbonyl group and a stereogenic centre with a phenyl group at the 4-position. In the laboratory, chemists attach this auxiliary to a substrate for a limited time, usually as an N-acyl thiazolidinethione. It then guides the diastereoselective formation of new stereocentres. When the transformation is complete, the auxiliary is cleaved from the product, leaving the newly built chiral framework.

Thiazolidinethione auxiliaries have several advantages over classical oxazolidinones. The thiocarbonyl group coordinates strongly to metals such as titanium and tin. Because of this, chemists can steer asymmetric aldol reactions toward the diastereomer they want by choosing the reaction conditions. The N-acyl bond in thiazolidinethiones is also generally easier to cleave. A range of nucleophiles can release the auxiliary and convert the product directly into an aldehyde, ester, amide, or acid. The phenyl group provides effective steric shielding, and the defined (R) configuration sets the direction of stereochemical induction.

In Indonesia, this auxiliary is relevant to research groups working on total synthesis, natural product chemistry, and the development of chiral building blocks. University organic chemistry laboratories and research institutes can use it in projects where reliable stereocontrol is essential, such as building polyketide-type fragments or optically active intermediates. It also suits advanced teaching and thesis work in asymmetric methodology, where students compare auxiliary-based strategies and study how metal choice and reaction conditions affect diastereoselectivity in carbon–carbon bond formation.

TCI brochures (PDF)

Chiral Auxiliaries and Optical Resolving Agents 2025-06-17 · p. 4

Related TCI products

Asymmetric aldol reactions: the thiocarbonyl group coordinates strongly to titanium or tin, so chemists can select the reaction conditions that favour the desired aldol diastereomer.
Diastereoselective synthesis of new stereocentres: once attached to a substrate as an N-acyl thiazolidinethione, the auxiliary directs bond formation through the steric shielding of its phenyl group.
Direct conversion to aldehydes, esters, amides, or acids: the N-acyl bond is relatively easy to cleave, so different nucleophiles can release the auxiliary and deliver the target functional group in one step.
Total synthesis and natural product chemistry: its predictable stereochemical induction from the defined (R) configuration helps research groups build complex chiral fragments reliably over multi-step routes.
Methodology research and advanced teaching: it is a useful alternative to classical oxazolidinone auxiliaries for comparative studies of stereocontrol, metal coordination effects, and auxiliary cleavage strategies.

Brand	TCI (product code P1959)
CAS number	110199-18-3
Molecular formula	—
Purity	—
Category	Chemistry > Asymmetric Synthesis > Chiral Auxiliaries
Pack sizes	as offered in the TCI catalogue for this product code
Physical form	refer to the TCI product label and Certificate of Analysis
Storage	follow the conditions on the TCI label and Safety Data Sheet

Store (R)-4-Phenylthiazolidine-2-thione in its original, tightly closed manufacturer container. Keep it in a cool, dry, well-ventilated area, away from direct sunlight, heat sources, moisture, and incompatible substances such as strong oxidising agents. If the material is repackaged, use clean, dry, chemically compatible glass containers with secure closures and clear labels. Always follow the storage conditions on the TCI label and Safety Data Sheet. When handling the material, wear suitable personal protective equipment, including a lab coat, safety glasses, and chemical-resistant gloves. Work in a fume hood to avoid inhaling dust or vapour. Do not let it come into contact with your skin or eyes. Dispose of residues and contaminated materials according to local regulations and institutional chemical waste procedures.

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