(4R)-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 150718
• Molecular Formular: C4H7NO2S
• Molecular Mass: 133.16888
• Monoisotopic Mass: 133.01974947
• SMILES: C1[C@H](NCS1)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1CSCN1
• InChI: InChI=1S/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1
• InChIKey: DZLNHFMRPBPULJ-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: (4R)-1,3-thiazolidine-4-carboxylic acid
• Synonyms: L-Thiaproline; L-4-Thiazolidinecarboxylic acid; (4S)-4-Thiazolidinecarboxylic Acid; (S)-4-Thiazolidinecarboxylic Acid; D-Thiazolidine-4-carboxylic Acid; D-Thiaproline; L-Thiazolidine-4-carboxylic acid; (R)-Thiazolidine-4-carboxylic acid; D-THIAZOLIDINE-4-CARBOXYLIC ACID; L-硫代脯氨酸; L-噻唑烷-4-羧酸

Database IDs

• CAS Number: 45521-09-3; 34592-47-7
• EC Number: 252-106-3
• MDL Number: MFCD00005212
• Beilstein Number: 81065
• Merck Index: 149445
• PubChem SID: 24900069; 24899900; 24889089; 162244879
• PubChem CID: 93176

CALCULATED PROPERTIES

• Acid pKa: 2.5915701
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.683327
• LogD (pH = 7.4): -2.8394518
• Log P: -2.6825848
• Molar Refractivity: 30.8241 cm^3
• Polarizability: 12.540595 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 190-200 °C (dec.)(lit.); 192-200°C dec.
• Optical Rotation: [α]20/D -101±2°, c = 1% in 1 M HCl; [α]20/D -141°, c = 1.3 in H2O; -141 (c=1.3 in water)

Safety Information

• RTECS: XJ5425500
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 20/21/22-36/37/38; 22-36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H312-H315-H319-H332-H335; H301-H315-H319-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥99.0% (T); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C4H7NO2S

DETAILS

Sigma Aldrich - T27502

Packaging
10, 100 g in poly bottle
Application
Used in peptide coupling reactions.1

Toronto Research Chemicals - T344205

A thiazolidine derivative with inhibitory effects on blood platelet aggregation. It is used in studies as a ligand for the catalytic asymmetric reduction of ketones with borane.

REFERENCES

• Satake, M. et al.: Experientia, 45, 1110 (1989)
• Hanessain, S. et al.: Can. J. Chem., 80, 885 (1989)