Shandong Huashang Chemical Co., Ltd. is a high-tech enterprise specializing in the research and development, manufacturing, and sales of fine chemicals. Headquartered in Jinan, Shandong, China, we are committed to delivering high-quality products to our global partners. Currently, over 90% of our products are exported to developed markets, including North America, Europe, Japan, South Korea, and the Middle East.
Product Description
4-Fluorothiophenol, also known as 4-Fluorobenzenethiol (CAS: 371-42-6), is an aromatic organosulfur compound with the linear formula FC?H?SH. It appears as a colorless transparent liquid at room temperature, featuring a pungent, thiol-like odor. The compound is insoluble in water but miscible with common organic solvents such as ethanol, ether, and chloroform. Its molecular structure consists of a benzene ring substituted with a fluorine atom at the 4-position and a thiol (-SH) group, endowing it with both nucleophilic reactivity (via -SH) and aromatic fluorination properties. It serves as a critical building block in pharmaceutical, agrochemical, and dye synthesis, with wide applications in organic synthesis and material modification.
Uses
Pharmaceutical Intermediate: As a key raw material for synthesizing fluorine-containing thiol drugs, it leverages the fluorine atom’s ability to enhance metabolic stability and target binding affinity of pharmaceutical molecules. It is widely used in the synthesis of anti-inflammatory, antiviral, and antitumor drugs, where the thiol group enables conjugation with active moieties to improve drug efficacy and bioavailability.
Agrochemical Synthesis: Employed in the production of pesticides and herbicides with high selectivity. The thiol group in its structure facilitates conjugation with pest-targeting moieties, enhancing the insecticidal and herbicidal activity while reducing environmental toxicity. It is also used as a precursor for synthesizing fungicides and plant growth regulators.
Dye & Material Chemistry: Acts as a precursor for fluorinated aromatic dyes and functional materials. Its thiol group enables surface modification of nanoparticles (such as gold, silver, and quantum dots) for the formation of self-assembled monolayers (SAMs), which are widely used in sensors, optoelectronic devices, and biological labeling. It also contributes to the synthesis of high-performance organic pigments with excellent light and thermal stability.
Chemical Research & Organic Synthesis: Used as a versatile reagent in organic synthesis, including cross-coupling reactions, thiol-ene click chemistry, and nucleophilic substitution reactions. It serves as a model compound for studying aromatic fluorination and thiol reactivity, providing valuable insights for the development of new synthetic methodologies. Additionally, it is used in the preparation of thiol-containing ligands for coordination chemistry research.
Molecular Formula & Structure
- Molecular Formula: C?H?FS
- Molecular Weight: 128.17 g/mol (128.171 g·mol?1, precise value)
- IUPAC Name: 4-Fluorobenzenethiol
- Synonyms: 4-Mercaptofluorobenzene; p-Fluorothiophenol; 4-Fluorobenzene-1-thiol; p-Fluorobenzenethiol; MFCD00004846; BRN 1905232; PubChem Substance ID: 24892674; EC Number: 206-737-6
- EC Number: 206-737-6
- CAS Number: 371-42-6
- SMILES Code: Fc1ccc(S)cc1
- Chemical Structure: The molecule consists of a benzene ring with para-substituted fluorine (F) and thiol (-SH) groups. The thiol hydrogen is acidic (pKa ≈ 6.5), enabling deprotonation to form thiolate anions that exhibit strong nucleophilicity. The fluorine atom on the benzene ring enhances the electron-withdrawing effect, regulating the reactivity of the thiol group and making it suitable for various organic transformations.
Physical & Chemical Properties
- Appearance: Colorless transparent liquid; may develop a slight yellow tint upon prolonged exposure to air or light due to oxidation.
- Melting Point: 43–46 °C (lit.); Boiling Point: 164–168 °C (700 mmHg), 162.3 ±13.0 °C (760 mmHg, predicted); Flash Point: 54 °C (closed cup); combustible liquid, poses fire hazard when exposed to open flames or high temperatures.
- Density: 1.203 g/mL (25 °C, lit.); Refractive Index: n??/D 1.548–1.550 (lit.); Solubility: <1 g/L in water; soluble in ethanol, ether, chloroform, benzene, and kerosene.
- Stability: Stable under cool, dry, and airtight conditions; decomposes slowly in strong acids and strong bases. It oxidizes upon prolonged air exposure, forming disulfide impurities (bis(4-fluorophenyl) disulfide). Avoid contact with oxidizing agents (such as hydrogen peroxide, potassium permanganate) to prevent accelerated oxidation.
- Toxicity: Irritant (GHS labeling: signal word "Warning", hazard statements H315 (causes skin irritation), H319 (causes serious eye irritation), H335 (may cause respiratory irritation)); swallowing may be harmful, and skin/eye contact can cause severe discomfort. It is toxic to aquatic organisms (H400) and may have long-term adverse effects on the aquatic environment (H410); precautionary statements include P264, P280, P302+P352, P305+P351+P338, P310, P332+P313, P362, P501.
Synthesis & Storage
- Synthesis: The main synthetic route involves the reduction of 4-fluorobenzenesulfonyl chloride with reducing agents such as zinc/hydrochloric acid or sodium sulfide. Alternatively, it can be prepared via nucleophilic substitution of 4-fluorohalobenzene (e.g., 4-fluorobromobenzene) with sodium hydrosulfide (NaSH) in polar solvents. The crude product is purified by distillation under reduced pressure to remove disulfide and other impurities, ensuring high purity.
- Storage: Sealed in amber glass bottles under a nitrogen atmosphere to prevent oxidation; store in a cool, dry, dark place with a recommended temperature ≤15 °C. Keep away from oxidizing agents, strong acids, open flames, and heat sources. Store separately from food and beverages. Shelf life: 12 months when unopened and stored properly; use promptly after opening to prevent oxidation and impurity formation.
- Safety: Operate in a well-ventilated fume hood to avoid inhalation of vapors. Wear nitrile gloves, chemical protective goggles, and a lab coat during operation. Avoid skin, eye, and mucous membrane contact; do not swallow or inhale the vapor. In case of skin contact, immediately wash the affected area with plenty of water and soap for at least 15 minutes; in case of eye contact, rinse cautiously with water for several minutes and seek medical advice immediately. Dispose of waste and contaminated containers in accordance with relevant environmental regulations and hazardous waste disposal standards.
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