Di-tert-butyl dicarbonate, with the CAS number 24424 - 99 - 5, is a widely used organic compound in the chemical industry. Its molecular formula is C₁₀H₁₈O₅, and the molecular weight is approximately 218.25 g/mol. It appears as a white crystalline solid with a melting point range of around 22 - 24 °C. This product is known for its high quality and is offered at the best price, making it an attractive option for various applications. It is soluble in common organic solvents such as dichloromethane, chloroform, and tetrahydrofuran, but has limited solubility in water.
Di-tert-butyl dicarbonate is an important reagent in organic synthesis. One of its most common uses is as a protecting group for amines in peptide synthesis. It can selectively protect the amino group of an amino acid, preventing unwanted side reactions during the peptide bond formation process. After the desired reaction is completed, the protecting group can be easily removed under mild acidic conditions, restoring the original amino group. In addition, it is also used in the synthesis of pharmaceutical intermediates, agrochemicals, and fine chemicals. It can be used to introduce the tert-butoxycarbonyl (Boc) group into various molecules, which can modify the physical and chemical properties of the target compounds, such as improving their solubility, stability, and bioavailability.
When using di-tert-butyl dicarbonate, appropriate safety measures should be taken. It should be stored in a cool, dry, and well-ventilated place, away from heat sources and ignition sources. Wear appropriate personal protective equipment, such as gloves and goggles, when handling this product. In a typical organic synthesis reaction, the amount of di-tert-butyl dicarbonate used usually depends on the molar ratio of the reactants. Generally, a slight excess of di-tert-butyl dicarbonate is used to ensure complete reaction. It is usually added slowly to the reaction mixture under stirring conditions to control the reaction rate. The reaction temperature and time also need to be carefully controlled according to the specific reaction requirements. After the reaction is completed, the product can be purified by methods such as extraction, distillation, or chromatography.
Let's consider a case in peptide synthesis. Suppose we want to synthesize a simple dipeptide, glycyl-alanine. First, we need to protect the amino group of glycine. Dissolve glycine in an appropriate organic solvent, such as dichloromethane, and add a base, such as triethylamine, to the solution. Then, slowly add di-tert-butyl dicarbonate to the reaction mixture under ice bath conditions. The reaction is allowed to proceed at room temperature for a certain period of time until the protection reaction is complete. The progress of the reaction can be monitored by thin-layer chromatography (TLC). After the protection of glycine is completed, the protected glycine is coupled with alanine using a coupling reagent, such as dicyclohexylcarbodiimide (DCC). The resulting dipeptide still has the Boc protecting group on the amino group of glycine. Finally, the Boc protecting group can be removed by treating the dipeptide with a mild acid, such as trifluoroacetic acid (TFA), to obtain the desired dipeptide, glycyl-alanine. This case demonstrates the importance and effectiveness of di-tert-butyl dicarbonate in peptide synthesis.
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