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This section provides an overview for diazomethane as well as their applications and principles. Also, please take a look at the list of 6 diazomethane manufacturers and their company rankings. Here are the top-ranked diazomethane companies as of December, 2024: 1.Sterling Pharma Solutions, 2.BenchChem, 3.SimSon Pharma Limited.
Table of Contents
Diazomethane is an organic compound with the molecular formula CH2N2.
It is classified as a diazo compound because it has a diazo group in its molecule. Diazomethane has the simplest structure among diazo compounds, and its CAS registration number is 334-88-3.
It has a molecular weight of 42.04, a melting point of -145°C, and a boiling point of -23°C. At room temperature, it exists as a yellow gas with a musty odor. It has a density of 1.4 (air = 1). It is highly explosive and may explode on impact, heat, light, or in the presence of alkali metals.
It reacts with water, but is relatively stable in ether or dioxane solutions. Otherwise, it is readily soluble in benzene, slightly soluble in ethanol and ethyl ether, but reacts slowly with alcohols and decomposes.
It is also harmful to the human body through skin irritation and inhalation, so it should be handled with care.
The main uses of diazomethane include methylating agent, agrochemical raw material, and pharmaceutical raw material. In organic synthesis laboratories, it is used for reactions such as O-methylation of carboxylic acids and phenolic hydroxy groups (to produce methyl ether and methyl ester derivatives) and C-methylation via epoxidation of ketones, among others.
Because of its explosive nature, it is usually used in ether or dioxane solutions, which are prepared for use, but safer and easier-to-handle alternatives are very often used.
Due to the delocalization of π-electrons, the Lewis structure of diazomethane is represented as a resonance mixture, and the molecular structure is a linear structure. It is a very unstable substance and, as mentioned above, can decompose explosively when subjected to shock, friction, or vibration.
Heating to 100°C or contact with rough surfaces are also factors that can induce explosion. Additionally, the presence of impurities or solids in undiluted liquids or concentrated solutions can also cause explosions under high-intensity light.
Diazomethane itself is not commercially available because it is a very unstable, dangerous, and difficult to handle substance. As mentioned above, it is usually used as an ether solution or dioxane solution, which is adjusted for use.
On the other hand, trimethylsilyl diazomethane ((CH3)3SiCHN2) is a stable, non explosive liquid with reactivity similar to that of diazomethane. Because it is easy to handle, it is also available commercially as a chemical reagent.
Except in special cases where diazomethane itself must be used, this is the most commonly used reagent, and it is also preferred from a safety standpoint. Trimethylsilyldiazomethane reagent products are usually 10% hexane solution, and are available in 5mL, 25mL, 100mL, etc. They are reagents that require refrigerated storage.
Diazomethane, as mentioned above, is explosive, so it is used as an ether or dioxane solution, adjusted for use. The general method of synthesis is to react acylated or sulfonated N-methyl-N-nitrosamines with a concentrated aqueous alkaline solution.
The specific experimental operation can be obtained by the following flow.
Diazomethane is a photolytic substance that produces methylene CH2. When reacted with acid chlorides, diazomethyl ketone or chloromethyl ketone is formed.
Reaction with active triple bonds of acetylenes and double bonds of ethylenes leads to 1,3-dipole addition reactions to form pyrazole or pyrazoline derivatives. It is also used in the ring expansion reaction of cyclic ketones in the Arndt-Eichstadt synthesis.
When used as an O-methylating agent for phenol or carboxylic acids, the reaction is generally carried out by stirring an ice-cold ether solution of an excess amount of diazomethane and adding it to a solution of phenol or carboxylic acid in small quantities.
*Including some distributors, etc.
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BenchChem, an American company located in Pasadena, California, is a supplier specializing in chemicals and biochemicals for laboratory and research and development use. The company’s product portfolio includes inhibitors, chemical reagents, bioactive chemicals, lead compounds, and catalysts. These products cater to various industries, including pharmaceutical companies, biotechnology firms, academic and research institutions, chemical and materials science researchers, as well as environmental and analytical laboratories. The company provides customer services, including contract manufacturing and analytical services.
Parchem was founded in 1999 and headquartered in Rochelle, New York. Parchem is a distributor of industrial chemicals. Parchem serves nutritional, personal care, pharmaceutical, and specialty chemical industries. Parchem offerings include coatings, adhesives, elastomers, industrial products, petrochemicals, oleochemicals, plastics, rubber, nutritional supplements, cosmetics, consumer products, catalysts, metallic salts, rare earths, flavors & fragrances, industrial & institutional, textiles, other food-related chemicals, dyes, finishes, chemicals for aerospace, oil gas drilling chemicals, electronics, and pharmaceuticals.
SimSon Pharma Limited, established in 2011 and headquartered in Mumbai, India, is a manufacturer and supplier of pharmaceutical reference materials. Their product range includes drug working standards, drug impurity standards, drug metabolites, and stable isotope labeled compounds. These provide a basis for comparison and validation, enabling pharmaceutical companies to produce safe and effective medications. The company's offerings serve specific purposes, such as calibrating analytical instruments and ensuring precise analytical results, identifying and quantifying impurities in drugs, understanding drug metabolism, and developing new drug therapies.
Trademill Technologies Pvt Ltd, founded in the United States in 1987, is a supplier of finished metal parts and assemblies and has ISO 9001 certification. The company's product portfolio includes CNC Machined Parts, Stamped and Formed Components, Turned and Milled Parts, Sheet Metal Fabrications and Extruded and Cast Components. It also provides services such as Design and Engineering Support, Prototyping and Rapid Manufacturing, Quality Control and Inspection, Surface Treatments and Coatings, and Custom Packaging and Labeling.
Ranking as of December 2024
Derivation Method| Rank | Company | Click Share |
|---|---|---|
| 1 | Sterling Pharma Solutions |
20.0%
|
| 2 | BenchChem |
20.0%
|
| 3 | SimSon Pharma Limited |
20.0%
|
| 4 | NINGBO INNO PHARMCHEM CO.,LTD. |
20.0%
|
| 5 | Parchem |
20.0%
|
Derivation Method
The ranking is calculated based on the click share within the diazomethane 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.
*Including some distributors, etc.
| Country | Number of Companies | Share (%) |
|---|---|---|
|
United States of America
|
2 | 50.0% |
|
India
|
1 | 25.0% |
China
|
1 | 25.0% |
