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| | S-Trityl-3-mercaptopropionic acid Basic information |
| Product Name: | S-Trityl-3-mercaptopropionic acid | | Synonyms: | 3-TRITYLMERCAPTO PROPIONIC ACID;3-TRITYLSULFANYL-PROPIONIC ACID;S-TRITYL-BETA-MERCAPTOPROPIONIC ACID;(TRT)SCH2CH2COOH;S-TRITYL-3-MERCAPTOPROPIONIC ACID 98+%;3-Tritymercaptopropionic];3-Tritylmercapto-Propionic acid (Trt)SCH2CH2COOH;S-TRITYL-B-MERCAPTOPROPIONIC ACID | | CAS: | 27144-18-9 | | MF: | C22H20O2S | | MW: | 348.46 | | EINECS: | | | Product Categories: | Other Reagents | | Mol File: | 27144-18-9.mol |  |
| | S-Trityl-3-mercaptopropionic acid Chemical Properties |
| Melting point | 211-213°C | | Boiling point | 503.8±38.0 °C(Predicted) | | density | 1+-.0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Chloroform (Slightly, Heated), DMSO (Soluble), Methanol (Slightly) | | pka | 4.59±0.10(Predicted) | | form | Solid | | color | Off-White | | Water Solubility | Partly miscible in water. | | Sensitive | Air Sensitive | | InChI | InChI=1S/C22H20O2S/c23-21(24)16-17-25-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15H,16-17H2,(H,23,24) | | InChIKey | AECGEIVNZGQBJT-UHFFFAOYSA-N | | SMILES | C(O)(=O)CCSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | | CAS DataBase Reference | 27144-18-9(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 26 | | WGK Germany | 3 | | F | 10-23 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Aquatic Chronic 4
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | S-Trityl-3-mercaptopropionic acid Usage And Synthesis |
| Chemical Properties | White to off-white powder | | Uses | Preparation and structural modification of 3-Tritylsulfanylpropionic Acid possesses antileukemic activity against leukemia. | | Synthesis | General procedure for the synthesis of 3-(triphenylmethylthio)propionic acid from triphenylmethanol and 3-mercaptopropionic acid:
1. 100 g of 3-mercaptopropionic acid (942.15 mmol) was dissolved in 300 mL of glacial acetic acid at room temperature.
2. 245.27 g of triphenylmethanol (942.15 mmol) was dissolved in 736.79 mL of tetrahydrofuran (THF) at room temperature.
3. Slowly add the solution obtained from step 1 to the solution from step 2.
4. 16.62 g of concentrated sulfuric acid (98%, 169.587 mmol) is added slowly and dropwise at 28° C to 30° C. The reaction mixture is insulated.
5. The reaction mixture was stirred under insulating conditions for 4 hours.
6. Upon completion of the reaction, 360 g of solid crude product was obtained by filtration.
7. The crude product was dissolved in 720 mL of N,N-dimethylformamide (DMF).
8. 5 times the volume of water was added to the solution, filtered and dried to give 295.5 g of refined product in 90% yield.
9. The structure of the product was confirmed by infrared spectroscopy (IR) and nuclear magnetic resonance (NMR). | | References | [1] Organic Letters, 2017, vol. 19, # 12, p. 3195 - 3198
[2] Patent: CN106380430, 2017, A. Location in patent: Paragraph 0017; 0018; 0019; 0020
[3] Chemical Communications, 2014, vol. 50, # 35, p. 4571 - 4574
[4] Australian Journal of Chemistry, 1990, vol. 43, # 3, p. 629 - 634
[5] Journal of Medicinal Chemistry, 2000, vol. 43, # 8, p. 1448 - 1455 |
| | S-Trityl-3-mercaptopropionic acid Preparation Products And Raw materials |
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