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This section provides an overview for imidazole as well as their applications and principles. Also, please take a look at the list of 14 imidazole manufacturers and their company rankings. Here are the top-ranked imidazole companies as of December, 2024: 1.Kishida Chemical Co.,Ltd., 2.Manus Aktteva Biopharma LLP, 3.Shilpa Chemspec International Pvt. Ltd..
Table of Contents
Imidazole is a type of heterocyclic compound containing two nitrogen atoms. Other names include 1H-imidazole, glyoxane and 1,3-diazole,
Imidazole is also referred to as a generic term for a group of compounds with substituents on the nitrogen or carbon forming the imidazole ring.
Imidazole is widely used industrially as a raw material for chemicals, agrochemicals, and pharmaceuticals. In particular, it is often used as a semiconductor encapsulant and adhesive, as it exhibits excellent properties in areas around electronic substrates where heat resistance is required.
It is are also widely used in various other industrial fields, such as curing agents and accelerators for epoxy resins, urethane foaming catalysts, rust inhibitors, rubber vulcanization accelerators, paints, adhesives, construction materials, and sporting goods.
As a base catalyst type curing agent or accelerator, it is characterized by its excellent storage stability, such as curing with the addition of a relatively small amount.
In pharmaceutical applications, imidazole is used in antifungal agents, and imidazoles with substituents attached to the imidazole ring are also used in many pharmaceuticals, including anti-ulcer, anti-hypertensive, and anti-asthmatic agents. In addition, imidazolium salts containing imidazolium cations, which are quaternary amines formed by alkyl addition to the nitrogen of imidazole, have become ionic liquids, neutralized salts with melting points near room temperature, and are attracting attention as green solvents, which are environmentally friendly solvents.
Imidazole is a white to pale yellow flaky solid with molecular formula C3H4N2 and molecular weight of 68.08. It has a melting point of 88~92°C, a boiling point of 256°C, and a flash point of 145°C.
Imidazole is sublimable. It is soluble in solvents of high polarity, easily soluble in water, methanol, and ethanol, soluble in pyridine and chloroform, insoluble in ether and benzene of low polarity, and nearly insoluble in hexane.
It forms complexes with many transition metal ions and functions as an excellent ligand. It is resistant to thermal decomposition and relatively stable against oxidizing and reducing agents. It exhibits strong aromaticity and is susceptible to hydrogen atom substitution reactions.
Imidazole retains its symmetrical structure by taking on a resonance structure even when the proton at position 1 is removed or the nitrogen at position 3 is protonated. This allows the charge to be dispersed without loss of aromaticity.
There are various derivatives with substituents attached to the imidazole ring, and these are called imidazoles. Substituents are attached to the nitrogen at the 1-position and the carbons at the 2-, 4-, and 5-positions, and it is possible to synthesize derivatives with different substituents at each position. The nitrogen at position 3 can also be cationized by nucleophilic substitution, but substituents can be attached.
Typical imidazoles include 2-methylimidazole, 2-ethyl-4-methylimidazole, and 2-phenylimidazole, where the prefix number indicates to which site of the ring the substituent is attached. Acylated imidazoles are sensitive to nucleophilic reactions and are used in the synthesis of carboxylic acid derivatives.
Imidazole is also commonly used as a base and catalyst in the protection of hydroxyl groups as silyl ethers by the action of silyl chlorides. Additionally, carbonyldiimidazoles (CDIs) are useful as carbonylating agents and amide condensing agents.
Imidazole can be produced by the reaction of glyoxal with aldehydes and ammonia, or by synthesis from ethylenediamine and nitriles.
1. Synthesis from glyoxal
The type of aldehyde or amine used as a raw material determines the substituent at the 1- and 2-positions.
OHC-CHO + R1-NH2 + R2CHO → R1R2C3H2N2 + 3H2O
2. Synthesis from ethylenediamine
The substituent at the 1- and 2-positions is determined by the substituent of the nitrile.
H2N-CH2CH2-NH2 + RCN → R2C3H4N2 + NH3 → R2C3H2N2 + H2
*Including some distributors, etc.
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Kishida Chemical Co. Ltd., established in 1924 and headquartered in Osaka, Japan, is a manufacturer of reagents and high-purity chemicals and also does drug discovery support activities. Its product portfolio includes fine chemicals, research chemicals, ionic liquid, organic micro-analytical reagents, and chemical reagents for analysis. The products support several industries, including reagent business, battery material, drug discovery, and life science. The company is ISO 14001 certified and supplies several companies worldwide, including Meterion Advanced Chemicals Inc., Acros Organics, ChemBridge Corporation, Decon Laboratories, and InerBioScreen Ltd.
Manus Aktteva Biopharma LLP, established in 2010 and headquartered in Ahmedabad, India, is a manufacturer, supplier, and exporter of pharmaceutical APIs, intermediates, and specialty chemicals. Their wide-ranging products cater to industries such as pharmaceutical, nutraceutical, and biotechnology. They offer Active Pharmaceutical Ingredients (APIs), the fundamental components used in various drug formulations, such as antibiotics, cardiovascular drugs, and anti-inflammatory drugs. The company also supplies specialty chemicals with unique properties applicable to diverse industries, from plastics to cosmetics manufacturing. Furthermore, the company offers custom synthesis services to meet the specific needs of their customers.
Shilpa Chemspec International Pvt. Ltd, established in 1982, is a manufacturer and wholesale trader of specialty chemicals and intermediates. This private company is based in Mumbai, India, and serves local and global clients. They distribute, import, and export specialty chemicals, papers, and boards, laminates, and coated foils. Their self-adhesive labels are used in various industries, including food and beverage, health and personal care, car, motor oil, and tyre. The company has recently ventured into contract manufacturing of intermediates used in bulk drugs, dyes, agrochemicals, and metal surface treatment chemicals.
Triown Chemie, established in 1996, is a chemical manufacturer, exporter, and trader based in Ahmedabad, India. The company offers a range of chemicals known for its purity, accurate pH-values, precise composition and extended shelf life. With an experienced professional team who ensure that their products meet international standards through rigorous testing procedures. They provide excellent products and customer service which allows them to expand their reach to regions including Europe, Asia, Latin America and China. Their transparent business practices, range of chemicals, advanced processing unit, robust R&D department and competitive pricing distinguish them from the competitors.
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.
SUVCHEM, established in 2004 and headquartered in Mumbai, India, is a manufacturer and exporter of laboratory chemicals and reagents. Their diverse product range includes organic and inorganic chemicals utilized in pharmaceuticals, plastics, water treatment, and more. They also offer biological stains and indicators for laboratory applications like cell culture and DNA analysis, along with culture media ingredients for growing microorganisms. SUVCHEM's products cater to schools, colleges, research laboratories, pharmaceutical and chemical companies, and other industries, supporting teaching, research, product development, and manufacturing processes across various sectors.
BASF SE, a manufacturer of polyurethane solutions, has been in business since 1865 and is headquartered in Ludwigshafen, Germany. They offer polyurethane products such as polyester polyols for CASE and footwear applications. The company delivers cutting-edge products while prioritizing environmental sustainability. With decades of expertise, they continue to drive creativity in the polyurethane sector, meeting the evolving needs of customers worldwide. With a long-standing history of success, BASF SE remains engaged on advancing technology and shaping the future of polyurethane applications.
Neil Chemical Industries, established in 2012 and headquartered in Kolhapur, India, specializes in specialty chemicals of pharma grade and serves as a manufacturer of imidazole in the form of flakes and its derivatives. The company's product portfolio includes N-methyl imidazole, 1-methyl imidazole, imidazole hydrochloride, imidazole epichlorohydrin polymer, iso amyl propropionate, and more. It also manufactures polyphosphoric acids and sodium bisulfite. The company offers products to a diverse range of industries such as the pharmaceutical, resin, and semiconductor sectors.
Nacalai Tesque Inc., founded in 1846 and headquartered in Kyoto, Japan, is a manufacturer of research chemicals, fine chemicals, diagnostics, and the related instruments. Some of its products include cytokines, nucleic acid electrophoresis, cell dissociation reagents, and sialic acid-related products, and it also offers custom and bulk service for bulk reagents and cell culture media. The company has more than 50 domestic distributors and several worldwide, including Asia, the Middle East, Oceania, Europe, and Africa. It is ISO 9001 and ISO 9002 certified, while the Kyoto South brand and Tesque factory are ISO 14001 certified.
Founded in 1981, Central Drug House Ltd. serves the scientific community via manufacturing and marketing a library of over 9,000 products to laboratory fine chemicals and dehydrated culture media with emphasis on purity and service. Examples are acids & bases, adsorbents, disinfectants, indicator papers, oils, and solvents. CDH provides bio chemicals, research chemicals, laboratory reagents, various solvents, stains & indicators, and dehydrated culture media. CDH is ISO 9001 certified and CDHs’ products are in compliance with specifications of IP, BP, USP, and EP standards.
naugraexport was established in 1951 and is a distributor and supplier of lab equipments based in Ambala Cantt, Haryana, India. The company's product portofolio offers various products such as zoom stereo binocular microscope, human anatomy models, flask erlenmeyer narrow neck glass, laser theodolite, and precision engineered cube mould. The products are used in various industries such as petrochemical, agriculture, semiconductor manufacture, pharmaceutical, and energy. The company has obtained the certificate of ISO 9001:2008 certification standards.
Shanghai Freemen Chemicals Co., Ltd., established in 1995 and headquartered in Shanghai, China, serves as a supplier of chemical products such as titanium dioxide, fluoride polymers, epoxy resins, and fine chemicals. The company offers a comprehensive product line, featuring ethyl vinyl ether, pivalic acid, aloe emodin, 3-aminomethyl oxetane, trimethyl orthoformate, and more. These products cater to industries such as fine chemicals, pharmaceuticals, agrochemicals, nutrition, and beyond. The company boasts a range of customers, including India Pesticide Limited, Biocon, Honeywell, Deccan, Syngenta, and others.
Ranking as of December 2024
Derivation Method| Rank | Company | Click Share |
|---|---|---|
| 1 | Kishida Chemical Co.,Ltd. |
28.2%
|
| 2 | Manus Aktteva Biopharma LLP |
10.0%
|
| 3 | Shilpa Chemspec International Pvt. Ltd. |
8.2%
|
| 4 | Triown Chemie |
8.2%
|
| 5 | Wuhan Bright Chemical Co. Ltd. |
7.3%
|
| 6 | Neil Chemical Industries |
7.3%
|
| 7 | SUVCHEM |
6.4%
|
| 8 | BASF SE |
5.5%
|
| 9 | naugraexport |
4.5%
|
| 10 | Merck |
4.5%
|
Derivation Method
The ranking is calculated based on the click share within the imidazole page as of December 2024. Click share is defined as the total number of clicks for all companies during the period divided by the number of clicks for each company.Number of Employees
Newly Established Company
Company with a History
*Including some distributors, etc.
| Country | Number of Companies | Share (%) |
|---|---|---|
|
India
|
6 | 66.7% |
|
Japan
|
2 | 22.2% |
China
|
1 | 11.1% |
