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This section provides an overview for fluoroglucinol as well as their applications and principles. Also, please take a look at the list of 5 fluoroglucinol manufacturers and their company rankings.
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Fluoroglucinol is a naturally occurring organic compound with the chemical formula C6H6O3.
Fluoroglucinol is biosynthesized by bacteria and plants and is present as glycosides in components within various plants. Acyl derivatives are found in the phloem of the fern Dryopteris arguta. Fluoroglucinol can be isolated from brown algae, and a type of tannin, phlorotannin, can be synthesized. Phlorotannin can also be obtained by hydrolysis of phenone derivatives with phloretin hydrolase.
| Chemical formula | C6H6O3 |
| Molecular weight | 126.11 |
| Melting point | 216 - 219°C |
Being polyfunctional, fluoroglucinol is useful as an intermediate in organic synthesis. It is mainly used as a synthetic raw material for pharmaceuticals and explosives.
For example, it is used as a synthetic raw material for flopropion. It can also be used as a coupling agent in printing because it quickly turns black when combined with diazo dyes. It shows a color reaction with lignin and is used as an analytical reagent. It is also used in the detection and quantification of pentoses and other compounds (the Torrens reaction), which is called the fluoroglucinol reaction.
Fluoroglucinol has a molecular weight of 126.11 and a melting point of 216-219 °C. The melting point of fluoroglucinol dihydrate at ambient pressure is 116-117 °C. Fluoroglucinol is sublimable. It is a weak tribasic acid with the first two pKa of 8.5 and 8.9.
It reacts with hydroxylamine to form an oxime. This is because fluoroglucinol, like enol, exists in equilibrium with the keto tautomer.
Fluoroglucinol also behaves like benzentriol, and methylation of the three hydroxyl groups yields 1,3,5-trimethoxybenzene.
Fluoroglucinol, also known as 1,3,5-benzentriol, is a polyphenol with three hydroxy groups substituted on the benzene ring and is a member of the benzenetriols or trihydroxybenzenes.
Fluoroglucinol is in pH-dependent chemical equilibrium. Two tautomers exist: 1,3,5-trihydroxybenzene (phenolic form) and 1,3,5-cyclohexatrione (ketone form). The keto tautomer of the spectroscopically neutral compound is undetectable. However, when deprotonated, the keto tautomer is predominant.
In organic synthesis, the reduction of 1,3,5-trinitrobenzene gives triaminobenzene, which is hydrolyzed by boiling the resulting hydrochloride salt with water. Normal aniline derivatives are inert to hydroxide ions, but triaminobenzene is easily hydrolyzed to an imine form due to its tautomerism.
1-(2,4,6-trihydroxyphenyl)ethanone can be synthesized by the Hoesch reaction of fluoroglucinol. The reaction of fluoroglucinol with isovaleroylnitrile in the presence of a zinc chloride catalyst yields leptospermone.
Fluoroglucinol reacts readily with low-temperature aqueous ammonia to form 5-aminoresorcinol (fluoramine). The reaction of fluoroglucinol with phloretic acid yields phloretin in 30% yield.
There are three isomers depending on the position of the hydroxy group: 1,2,4-benzenetriol and 1,2,3-benzenetriol. 1,2,4-benzenetriol is also called hydroxyquinol and 1,2,3-benzenetriol is called pyrogallol.
*Including some distributors, etc.
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Kanto Chemical Co. Inc., founded in 1944 and headquartered in Tokyo, Japan, is a reagent manufacturer with overseas affiliates in other countries, including China, France, USA, Taiwan, and Malaysia. Its product portfolio includes analytical reagents, ionic liquids, Iodine compounds, ultra-pure chemicals, and water analysis kits. The company is also developing regenerative medicine and genetics reagents and has over 50,000 products. It has several certifications, including ISO 9001, acquired in 1994, making it the first Japanese company in the reagent industry. Other certifications are ISO 14001, ISO 13485, and ISO/IEC 17025.
FujiFilm Wako Pure Chemical Corporation, founded in 1922 and headquartered in Osaka, Japan, is a manufacturer of laboratory chemicals, specialty chemicals, and clinical diagnostic reagents. The company has three business domains, namely laboratory chemicals, specialty chemicals, and clinical diagnostic reagents, and some of its products include biochemistry reagents, blood transfusion test drugs, battery materials, polymer-related materials, and general reagents. The products are useful in various fields, including electronic, cosmetic, polymeric, pharmaceutical, and medical care. It acquired Sibayagi Co. Ltd. in 2015 and provides custom manufacturing to meet customer requirements.
Merck, started in 1668 and based in Darmstadt, Germany, is a supplier of solutions and services for research, development, and manufacture of pharmaceutical and biotechnological drug therapies. The company serves the life science industry and has a broad portfolio of 300,000 products, including biopharmaceutical manufacturing, industrial microbiology, reagent, life science research, and water purification products. It is available in 66 countries, brings together six brands, and has several ISO certifications, including ISO 13485, ISO 14001, ISO 13485, and ISO 50001.
Millipore Sigma, formerly known as Sigma-Aldrich, was created in 175 through the merger of Sigma Chemical Company and Aldrich Chemical company and today is a subsidiary of Merck. Millipore Sigma is a life science and biotechnology company serving the industry with several products and services. Some of their product categories include peptide synthesis materials, biochemicals, building blocks, catalysts, chemical biology, chemical synthesis, flavors & fragrances, formulation, lab chemicals, lab safety, APIs, and stable isotopes. Services include characterization, contract manufacturing, custom products, software, support, testing, and mRNA development & manufacturing.
HAZMAT Resource, Inc., located in Irvine, California, USA, is a distributor of hazardous materials response equipment and materials. They specialize in personal protective equipment (PPE), testing devices, and technical reference materials for hazardous materials (hazmat) response. Their product range includes PPE such as suits, gloves, boots, and respirators to safeguard hazmat responders from dangerous substances. They offer various testing devices like meters, detectors, and kits for precise identification and measurement of hazardous materials. Additionally, the company provides technical reference materials like books, manuals, and software, equipping responders with essential knowledge on hazardous material properties and safe handling procedures.
Number of Employees
Newly Established Company
Company with a History
*Including some distributors, etc.
| Country | Number of Companies | Share (%) |
|---|---|---|
|
Japan
|
2 | 100.0% |
