苯硫酚
[CAS# 108-98-5]

基本信息

• 产品分类: 有机原料 >> 醇、酚、酚醇类化合物及衍生物 >> 酚及其卤化、磺化、硝化或亚硝化衍生物
• 产品名称: 苯硫酚
• 英文名: Thiophenol
• 别名: Benzenethiol; Phenyl mercaptan
• 分子式: C₆H₆S
• 分子量: 110.18
• CAS 登录号: 108-98-5
• EC 号码: 203-635-3
• FEMA 登录号: 3616
• 分子行输入简码SMILES: C1=CC=C(C=C1)S

物理化学性质

• 密度: 1.078
• 熔点: -15 °C
• 沸点: 167-169 °C
• 折射率: 1.588-1.59
• 闪点: 50 °C
• 水溶性: 不溶

安全数据

• 危险品标志: GHS02;GHS05;GHS06;GHS07;GHS09 危险
• 危害标签: H226-H300-H301-H310-H311-H314-H315-H318-H330-H400-H410
• 防护标签: P210-P233-P240-P241-P242-P243-P260-P262-P264-P264+P265-P270-P271-P273-P280-P284-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P320-P321-P330-P332+P317-P361+P364-P362+P364-P363-P370+P378-P391-P403+P233-P403+P235-P405-P501

危害分类

危害	分类	类别码	危害标签
易燃液体	Flam. Liq.	3	H226
急性毒性	Acute Tox.	1	H330
急性毒性	Acute Tox.	2	H300
皮肤刺激	Skin Irrit.	2	H315
严重眼损伤	Eye Dam.	1	H318
对水生环境急性有害	Aquatic Acute	1	H400
对水生环境长期有害	Aquatic Chronic	1	H410
急性毒性	Acute Tox.	3	H311
急性毒性	Acute Tox.	2	H310
急性毒性	Acute Tox.	3	H301
皮肤腐蚀	Skin Corr.	1C	H314
眼刺激	Eye Irrit.	2	H319
特定目标器官毒性—单次接触	STOT SE	2	H371
特定目标器官毒性—单次接触	STOT SE	3	H335
特定目标器官毒性—重复接触	STOT RE	1	H372
生殖毒性	Repr.	2	H361
急性毒性	Acute Tox.	2	H330
易燃固体	Flam. Sol.	1	H228
易燃液体	Flam. Liq.	4	H227
眼刺激	Eye Irrit.	2A	H319
特定目标器官毒性—单次接触	STOT SE	3	H371
皮肤腐蚀	Skin Corr.	1B	H314

• 危险品运输编号: UN 2337

是否危险化学品？

是，请看详情。

发现和应用

Thiophenol, also known as mercaptobenzene or benzenethiol, is a chemical compound with the chemical formula C₆H₅SH. It is characterized by a benzene ring bonded to a sulfur atom and a thiol (-SH) functional group. Thiophenol was first synthesized in the 19th century, when chemists were exploring the properties and reactions of thiols and aromatic compounds. Its discovery marked an important development in organic chemistry, especially in the understanding of sulfur-containing organic molecules. Thiophenol consists of a benzene ring (C₆H₅-) to which is attached a sulfur atom (-S-) and a hydrogen atom (-H). It is a colorless to pale yellow liquid with a strong malodor reminiscent of rotting cabbage, which is typical of thiol compounds.

Thiophenol is widely used as a building block in organic synthesis, especially in the production of pharmaceuticals, agrochemicals, and dyes. Its sulfur-containing functional group promotes a variety of chemical reactions, including nucleophilic substitution and metal complex formation.

It is a key intermediate in the synthesis of other sulfur-containing compounds such as thiophenolates and disulfides. These intermediates can be used to make rubber additives, pesticides, and antioxidants.

The reactivity and stability of thiophenols make them valuable in industrial processes, including the production of specialty chemicals and polymer additives. It helps modify polymer surfaces and synthesize materials with specific chemical and physical properties.

Thiophenols are toxic if inhaled, ingested, or absorbed through the skin. Proper handling and ventilation are essential to prevent exposure to its vapor or liquid form. The strong odor of thiophenols is easily detectable even at low concentrations and serves as a warning of potential exposure.

Thiophenols and their derivatives are biodegradable in soil and water and have reduced environmental persistence compared to some other aromatic compounds. Due to their toxicity and environmental impact, the use and disposal of thiophenols are regulated in different jurisdictions to minimize potential hazards.

References

Holleman, A. F., Wiberg, E., & Wiberg, N. (2001). Inorganic Chemistry. Academic Press.
Clayden, J., Greeves, N., Warren, S., & Wothers, P. (2001). Organic Chemistry. Oxford University Press.
Bessette, D., & Goodgame, D. M. (1997). Thiophenol. In Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. 苯硫酚，也称为巯基苯或苯硫醇，是一种化学式为 C₆H₅SH 的化合物。它的特征是苯环与硫原子结合，并具有硫醇 (-SH) 官能团。苯硫酚最早是在 19 世纪合成的，当时化学家们正在探索硫醇和芳香族化合物的性质和反应。它的发现标志着有机化学的重要发展，特别是在理解含硫有机分子方面。硫酚由一个苯环 (C₆H₅-) 和一个与之相连的硫原子 (-S-) 和一个氢原子 (-H) 组成。它是一种无色至淡黄色液体，具有强烈的恶臭，让人联想到腐烂的卷心菜，这是硫醇化合物的典型特征。

硫酚被广泛用作有机合成的基石，特别是在药物、农用化学品和染料的生产中。其含硫官能团促进各种化学反应，包括亲核取代和金属配合物形成。

它是合成其他含硫化合物（如硫酚盐和二硫化物）的关键中间体。这些中间体可用于制造橡胶添加剂、农药和抗氧化剂。

硫酚的反应性和稳定性使其在工业过程中具有重要价值，包括生产特种化学品和聚合物添加剂。它有助于改性聚合物表面和合成具有特定化学和物理性质的材料。

硫酚如果吸入、摄入或通过皮肤吸收会产生毒性。正确的处理和通风对于防止接触其蒸气或液体形式至关重要。硫酚的强烈气味即使在低浓度下也容易被检测到，可作为潜在接触的警告。

苯硫酚及其衍生物可在土壤和水中发生生物降解，与其他一些芳香族化合物相比，其环境持久性有所降低。由于苯硫酚具有毒性和环境影响，因此不同司法管辖区对其使用和处置进行了监管，以尽量减少潜在危害。

参考文献

2018. XPS Analysis of 2- and 3-Aminothiophenol Grafted on Silicon (111) Hydride Surfaces. Molecules.
DOI: 10.3390/molecules23102712

2013. Peptide Release, Side-Chain Deprotection, Work-Up, and Isolation. Methods in Molecular Biology.
DOI: 10.1007/978-1-62703-544-6_3

2003. Mechanistic Studies of the Tellurium(II)/Tellurium(IV) Redox Cycle in Thiol Peroxidase-like Reactions of Diorganotellurides in Methanol. Journal of the American Chemical Society.
DOI: 10.1021/ja029590m