Overview
Trihydroxybenzene refers to three isomeric compounds with the molecular formula C6H6O3: 1,2,3-trihydroxybenzene (pyrogallol), 1,2,4-trihydroxybenzene (hydroxyhydroquinone), and 1,3,5-trihydroxybenzene (phloroglucinol). These compounds are aromatic phenols with distinct chemical and physical properties. Phloroglucinol is the most stable and widely used isomer, known for its role in organic synthesis and pharmaceuticals. Pyrogallol is a strong reducing agent, while hydroxyhydroquinone is less common but finds niche applications in dyes and analytical chemistry. Trihydroxybenzenes are typically synthesized from benzene derivatives through hydroxylation or other substitution reactions. Their reactivity and ability to form complexes with metals make them valuable in industrial and laboratory settings. Proper identification of the specific isomer is critical for applications, as their properties and toxicity vary.
Physical and Chemical Properties
Trihydroxybenzenes are crystalline solids with varying solubility in water and organic solvents. Phloroglucinol (1,3,5-isomer) is the most water-soluble, while pyrogallol (1,2,3-isomer) oxidizes readily in air, turning brown. All isomers exhibit phenolic properties, including acidity and the ability to form colored complexes with iron(III) ions. The 1,3,5-isomer is particularly noted for its tautomeric equilibrium, existing in both keto and enol forms. Thermal stability varies among the isomers, with phloroglucinol being the most stable. Pyrogallol decomposes upon heating, releasing toxic fumes. The density, melting points, and boiling points are isomer-dependent, as reflected in the infobox. These properties influence their handling, storage, and application in industrial processes.
Main Applications
Trihydroxybenzenes are used in diverse industries. Phloroglucinol is a key intermediate in pharmaceuticals, particularly for antispasmodic drugs and flavonoid synthesis. It also serves as a coupling agent in dyes and a reagent in analytical chemistry. Pyrogallol is employed in hair dyes, photographic developers, and as an oxygen scavenger. The 1,2,4-isomer is less common but finds use in specialty dyes and as a reducing agent. In organic synthesis, these compounds act as building blocks for polyphenols and other complex molecules. Their chelating properties are exploited in metal extraction and corrosion inhibition. The choice of isomer depends on the specific reaction or application, emphasizing the need for precise procurement and handling.
Safety and Storage
Trihydroxybenzenes require careful handling due to their irritant and toxic properties. Pyrogallol is particularly hazardous, causing skin burns and systemic toxicity upon ingestion or inhalation. Phloroglucinol is less toxic but still requires protective equipment (gloves, goggles) during handling. All isomers should be stored in airtight containers, away from light and oxidizing agents, to prevent degradation. Spills should be neutralized with appropriate absorbents, and contaminated areas washed thoroughly. Disposal must comply with local regulations for phenolic compounds. Safety data sheets (SDS) should be reviewed before use, and workplace exposure limits (e.g., OSHA, ACGIH) adhered to.
B2B Procurement Guide
When procuring trihydroxybenzenes, specify the isomer (CAS number) and required purity (e.g., technical grade, ≥99%). Suppliers should provide certificates of analysis (CoA) and material safety data sheets (MSDS). Bulk purchases (25 kg drums or larger) typically offer cost savings, but verify storage conditions to prevent degradation. Reliable suppliers include chemical distributors like Sigma-Aldrich, TCI, and Alfa Aesar. For industrial-scale procurement, direct manufacturer contracts (e.g., Merck, BASF) may be preferable. Prices vary by isomer and quantity, with phloroglucinol generally commanding a higher price due to pharmaceutical demand. Request samples for quality testing before large orders.
Related Manufacturers
- 主营：亚硝酸钠、乙酸、氢氧化钠、三氟乙酸、三氟乙酸酐、三氯化铁、三氟乙酸乙酯、柠檬酸、柠檬酸钠、苯甲酸钠、无水亚硫酸钠
- 主营：三羟基、对照品、标准品
- 主营：苄基三甲基氯化铵、聚苯胺、脯氨酸甲酯盐酸盐
- 主营：聚乙烯亚胺、TS-1钛硅分子筛、5-甲基靛红、三甘醇二异辛酸酯3G8、三硫代碳酸钠40%、六氯环三磷腈、烷基苯磺酸酯、苯基次磷酸钠、甲巯咪唑、吡啶硫酮锌、焦磷酸哌嗪、热敏材料、油酸甲酯、曲酸
- 主营：红色素-16、聚乙烯亚胺、巯基苯并噻唑钠、三硫代碳酸钠、三乙二醇二异辛酸酯、L-丙交酯、乙交酯、石油酯-T50、多元醇苯甲酸酯、热压敏染料、光稳定剂、高分子降解材料
- 主营：叔碳酸、十八醛、溶菌酶、癸二醇、邻苯二甲、乙基碳二、羟基癸酸、烷二甲醇、癸烷撑二醇、10-羟基羊蜡酸、海藻糖、氨基丙基、氢路噻嗪、正十七烷、谷胱甘肽、松果体素、vc磷酸酯镁、2-甲基丁醛、朱栾倍半萜、丁烷四乙酸、表面活性剂、缩水甘油邻、氢氯噻嗪杂质、盐酸邻菲罗啉、壳聚糖季铵盐
- 主营：固体酸催化剂、重组胶原蛋白、硅油、全氟三丁胺、特种硅油、聚硅氮烷、硼酸铝晶须、碳化硅晶须、t-BAMBP萃取剂
- 主营：化学品、香精香料、试剂、三羟基二苯甲酮、中间体、有机硅、橡胶树脂、催化剂、纳米材料
- 主营：异丙醇铝、纳米勃姆石、隐色结晶紫、全氟三丁胺、二苄叉山梨醇、六氟丙烯二聚体、六氟环氧丙烷二聚体、二异戊基硫醚、邻菲罗啉
- 主营：杜仲素、对位酯、丙烯酸酯、二氧化硫脲、二苯基硅二醇、乙基麦芽酚、饲料添加剂、油酸基硬脂酸
- 主营：磷钼酸、艾拉莫德中间体、光引发剂、6-二羟基吲哚、甲基丙二酸、聚二羟基吲哚、2-辛基十二醇、苯芴醇、溴芬酸钠中间体、樟脑醌、钼酸钾、丝素蛋白、盐酸胍、β-丙氨酸甲酯盐酸盐、7-去氢胆固醇、甘氨胆酸钠盐、半叶素、胆固醇、蛋白酶K、D-荧光素钾盐、光引发剂LAP、BIS-TRIS、甲基丙烯酸氧杂环丁烷
- 主营：麦芽糖酸、苯氧基环磷腈、甲巯基四氮唑
- 主营：食品添加剂、饲料添加剂、原料中间体、三羟基二苯甲酮、去氧胆酸钠、肌酸酐、氨甲环酸、甘氨胆酸
- 主营：阻燃剂、乙酸镍、乙酸镝、庚二酸、硫酸锂、硫酸锶、溴氨酸、香茅醇、肌氨酸、锂电池、四氢萘、磷酸铬、碳酸镁、碳酸镍、防冻剂、磷酸铝、叔丁醇、氟苯基、浮选剂、稀释剂、羟乙基、去除剂、除磷剂、十八烯、蛋白酶
- 主营：酒渣碱、异常山乙素、芦丁标准品、三羟基二苯甲酮、对照品标准品