21243-09-4

Basic information

• Product Name: 3-[(2-FLUOROPHENYL)THIO]PROPANOIC ACID
• Synonyms: 3-(2-fluorophenyl)sulfanylpropanoate
• CAS NO: 21243-09-4
• Molecular Formula: C₉H₉FO₂S
• Molecular Weight: 199.22200
• Mol File: 21243-09-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 67-68 °C
• Boiling Point: 323.6oC at 760 mmHg
• Flash Point: 149.5oC
• Appearance: /
• Density: 1.3g/cm3
• Vapor Pressure: 0.000107mmHg at 25°C
• Refractive Index: 1.573
• PKA: 4.22±0.10(Predicted)
• CAS DataBase Reference: 3-[(2-FLUOROPHENYL)THIO]PROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(2-FLUOROPHENYL)THIO]PROPANOIC ACID(21243-09-4)
• EPA Substance Registry System: 3-[(2-FLUOROPHENYL)THIO]PROPANOIC ACID(21243-09-4)

Safety Data

• Hazardous Substances Data: 21243-09-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H9FO2S/c10-7-3-1-2-4-8(7)13-6-5-9(11)12/h1-4H,5-6H2,(H,11,12)

Upstream product

• 590-92-1 3-Bromopropionic acid 
• 2557-78-0 2-fluorothiophenol 
• 107-94-8 chloropropionic acid 
• 79-10-7 acrylic acid 

Downstream Products

• 1421435-06-4 2-[2-(8-fluorothiochroman-4-ylidene)hydrazinyl]-5-phenylthiazole 
• 21243-12-9 8-fluoro-thiochroman-4-one 

Relevant articles and documents

Synthesis and anticancer activities of thiosemicarbazones derivatives of thiochromanones and related scaffolds

A series of novel thiosemicarbazone analogs (4a–t, 6a–j) were synthesized and evaluated for their cytotoxic activities. The obtained results showed that thiochromanone-based thiosemicarbazones substituted primarily at the C-8 position exhibited higher cytotoxicity than the corresponding 1,1-dioxo-thiochromanone-, benzothiazepine-, and 1,1-dioxo-benzothiazepine-based analogs. Significantly, compound 4c (8-fluoro thiochromanone thiosemicarbazone) was found to be the most active and exhibited potent cytotoxicity against the MCF-7, SK-mel-2, and DU145 cancer cell lines, with IC50 values of 0.42, 0.58, and 0.43 μM, respectively. In addition, the mechanism of compound 4c induced MCF-7 cell apoptosis was preliminarily investigated through cell cycle, Annexin V-FITC/PI staining, and ROS assays, indicating that compound 4c may exert its anticancer property through ROS-mediated apoptosis.

Cu-Catalyzed Conjugate Addition of Grignard Reagents to Thiochromones: An Enantioselective Pathway for Accessing 2-Alkylthiochromanones

The enantioselective incorporation of alkyl groups in thiochromones was realized for the first time by a Cu/(R, S)-PPF-P t Bu 2 -catalyzed conjugate addition of Grignard reagents to thiochromones. With this method, a series of 2-methylthiochromanones were obtained in good yields (up to 96% yield) with moderate-to-good ee values (up to 87% ee). The established method expedites the synthesis of a large library of chiral thiochromanones for further synthetic applications and biological studies.

Ionic liquid catalyzed synthesis of 2-(indole-3-yl)-thiochroman-4-ones and their novel antifungal activities

2-(Indole-3-yl)-thiochroman-4-ones were synthesized via ionic liquid and tested for in vitro antifungal activity. The contribution of ionic liquid to Michael addition reaction is significant. Structures of all compounds are elucidated by 1H NMR, 13C NMR and HRMS. Most of these compounds showed better antifungal activity than fluconazole. The results suggest that 2-(indole-3-yl)-thiochroman-4-ones would be efficient antifungal agents.