Dimethylcarbamoyl chloride(https://www.bloomtechz.com/synthetic-chemical/organic-intermediates/dimethylcarbamoyl-chloride-cas-79-44-7.html), chemical formula C3H6ClNO, CAS 79-44-7. At normal temperature, it is a colorless to slightly yellow liquid, and it is a non-volatile liquid. The common form is a colorless transparent liquid. Its appearance can be compared to common organochlorine compounds. Due to its strong pungent nature, DMF-Cl's odor is often described as pungent or pungent. Almost insoluble in water, it reacts with water to form dimethyl carbamic acid. However, it has good solubility in many organic solvents, such as ether, chloroform, methanol, ethanol, etc. This solubility makes DMF-Cl have a wide range of applications in organic synthesis and chemical reactions. It does not evaporate easily at room temperature and can be stored and handled in liquid form. It is important to note that due to its pungent odor and corrosive nature, proper safety measures need to be taken when using and handling it. It can be used as a synthetic intermediate of dyes and pigments, and can obtain carbaamide dyes with different colors, which are widely used in textiles, leather, inks and plastics and other fields. It is also commonly used in chemical analysis to enhance the detection sensitivity of target compounds in chromatographic analysis.
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The laboratory synthesis method of Dimethylcarbamoyl chloride (dimethylcarbamoyl chloride, also known as DMF-Cl) usually uses Dimethylformamide (DMF) and Thionyl chloride (SOCl2) or Phosgene (COCl2).
Method 1: Reaction of Dimethylformamide and Thionyl chloride
step:
1. Prepare an anhydrous environment: Prepare an anhydrous environment under a dry inert atmosphere, such as nitrogen or dry solvent. Make sure all instruments, containers and reagents are dry.
2. Reactant preparation: Mix Dimethylformamide (DMF) and Thionyl chloride (SOCl2) according to the molar ratio. Typically, 1 equimolar DMF to 2 equimolar SOCl2 is used.
3. Reaction: Slowly add the prepared mixture into a cooled anhydrous solvent (such as methylene chloride or benzene). The reaction mixture is stirred and the temperature of the reaction is controlled, usually below room temperature. As the reaction proceeds, you will observe gas evolution (SO2) and the reaction solution becoming cloudy.
4. The end of the reaction: The reaction time varies according to the experimental conditions, generally several hours. The reaction was nearly complete when the cloudy reaction mixture gradually became clear.
5. Product separation: After the reaction is completed, the target product Dimethylcarbamoyl chloride is separated by distillation or filtration. Often, the solvent needs to be removed and the product purified.
The chemical reaction formula of the reaction between Dimethylformamide and Thionyl chloride:
(CH3)2NC(O)H + SOCl2 → (CH3)2NCOCl + SO2 + HCl
Method 2: Reaction of Dimethylamine and Phosgene
step:
1. Safety measures: Because Phosgene is highly toxic, it must be operated under strict safety conditions. Before performing this reaction, make sure you have taken proper safety precautions and perform the experiment in a well-ventilated environment.
2. Prepare an anhydrous environment: Prepare an anhydrous environment under a dry inert atmosphere, such as nitrogen or dry solvent. Make sure all instruments, containers and reagents are dry.
3. Reactant preparation: Mix Dimethylamine (CH3)2NH) and Phosgene (COCl2) according to the molar ratio. Usually, use 1 equimole of Dimethylamine corresponding to 1 equimole of Phosgene.
4. Reaction: Slowly add the prepared mixture of Dimethylamine and Phosgene into a cooled anhydrous solvent (such as dichloromethane or benzene). Gas evolution (HCl) occurs during the reaction and the reaction mixture becomes cloudy.
5. The end of the reaction: The reaction time varies according to the experimental conditions, generally several hours. The reaction was nearly complete when the reaction mixture gradually became clear.
6. Product separation: After the reaction is completed, the target product Dimethylcarbamoyl chloride is separated by distillation or filtration. Often, the solvent needs to be removed and the product purified.
The chemical reaction formula of the reaction between Dimethylamine and Phosgene:
(CH3)2NH + COCl2 → (CH3)2NCOCl + 2HCl
History of discovery of Dimethylcarbamoyl chloride:
The earliest discovery of Dimethylcarbamoyl chloride can be traced back to the early 20th century. According to literature records, in 1906, German chemist Kurt H. Meyer synthesized Dimethylcarbamoyl chloride for the first time. Meyer made the compound in his laboratory by reacting dimethylamine with thionyl chloride. He named it Dimethylcarbonyl chloride, and described the synthesis method and some physical properties in detail.
With the establishment of the synthesis method of Dimethylcarbamoyl chloride, researchers began to explore its chemical properties and application fields. In earlier studies, it was found that Dimethylcarbamoyl chloride could be hydrolyzed by alkaline agents such as sodium hydroxide to generate Dimethylcarbamate.
In the 1920s, Dimethylcarbamoyl chloride began to be used to synthesize many kinds of compounds. Studies have shown that dimethylcarbamoyl chloride reacts with amine compounds to form amide compounds, which provides a way for the synthesis of a large number of amine compounds. In addition, Dimethylcarbamoyl chloride can also be used as a chlorinating agent to react with certain alcohols to form ester compounds.
With the in-depth research on Dimethylcarbamoyl chloride, people have gradually discovered its wide application in the fields of organic synthesis and medicine. Dimethylcarbamoyl chloride can be used as an important reagent in a variety of synthetic reactions, such as carbamoylation reactions, substitution reactions, condensation reactions, etc. At the same time, it is also an important intermediate in the synthesis of many drugs.
For example, Dimethylcarbamoyl chloride can be used in the synthesis of antibiotics, pesticides, dyes and fragrance substances, etc. In the field of medicine, Dimethylcarbamoyl chloride can be used to prepare antiepileptic drugs, antineoplastic drugs, antidepressant drugs, etc. In addition, Dimethylcarbamoyl chloride can also be used in the synthesis of polyurethane resins, textile additives, etc.
The discovery and application of dimethylcarbamoyl chloride have greatly benefited researchers in the fields of organic synthetic chemistry and medicinal chemistry. The study of its structure and reaction properties has promoted the development of the field of organic chemistry and provided an important basis for the development of new drugs and new materials.
To sum up, Dimethylcarbamoyl chloride was first synthesized by German chemist Kurt H. Meyer in the early 20th century. Subsequently, people gradually discovered its important applications in the fields of organic synthesis and medicine. So far, the research on Dimethylcarbamoyl chloride is still going on, in order to seek new synthesis methods and application fields.