5-bromo-1H-pyrazolo[3,4-b]pyrazin-3-amine cas 1242336-77-1white powder support customized synthesis

This is a very important organic synthesis intermediate and reagent, especially in green chemistry and organic synthesis methodologies.
The following is a detailed introduction to this compound:
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1. Basic Information
· Chinese name: 2-Chloro-1,3-dimethylimidazolinium Chloride
· English name: 2-Chloro-1,3-dimethylimidazolinium Chloride
· Common abbreviation: DMC or CIMC
· CAS number: 1242336-77-1
· Molecular formula: C₅H₁₀Cl₂N₂
· Molecular weight: 169.05 g/mol
2. Chemical Structure and Properties
· Structural characteristics: It is an imidazoline salt compound, containing two chlorine atoms in its structure. One of the chlorines is connected to a carbon atom on the ring and has high reactivity; the other chlorine exists as an anion (Cl⁻).
· Appearance: Usually, it is a white to off-white crystalline powder.
· Solubility: Easily soluble in polar organic solvents such as dichloromethane, acetonitrile, N,N-dimethylformamide (DMF), etc. It has a certain degree of solubility in water but will slowly hydrolyze.
· Stability: Sensitive to air and moisture. It is usually stored in a dry and cool place and operated under the protection of inert gases (such as nitrogen or argon).
3. Main Applications and Reaction Mechanism
The core function of DMC is to act as an efficient and mild dehydrating condensing agent and activator. Its reactivity mainly stems from the chlorine atom on its ring, which is a good leaving group and can react with carboxylic acids to form highly active intermediates.
Main application fields:
1. Formation of amide bonds:
· This is the most important and widely used application of DMC. It can efficiently catalyze the condensation of carboxylic acids with amine compounds to form amides, which is an important method for synthesizing drug molecules and polymers.
· Advantages: Compared with traditional condensation agents (such as DCC, EDC·HCl), the reaction conditions of DMC are milder, the by-product (1,3-dimethylimidazolidin-2-one) is easy to remove, and there is no risk of causing allergies.
2. Esterification reaction:
· It can be used for the esterification reaction of carboxylic acids and alcohols, especially in substrates with high steric hindrance or sensitivity to acids.
3. Synthesis of heterocyclic compounds:
· As a cyclization dehydration agent, it is used to construct heterocyclic structures such as lactones and amides.
4. As a precursor of Vilsmeier-Haack reagent:
· When reacted with amide solvents such as DMC, it can in situ generate Vilsmeier reagent for acylation reactions.
Reaction mechanism overview (taking amide synthesis as an example):
· Step 1: The chlorine atom in DMC attacks the carbonyl carbon of the carboxylic acid, forming a highly active acyl oxime imidazoline cation intermediate.
· Step 2: The amine nucleophilically attacks this intermediate, removing one molecule of 1,3-dimethylimidazolidin-2-one, generating the target amide.
4. Advantages and Features
· High atom economy: The reaction by-products are only 1,3-dimethylimidazolidin-2-one, which is soluble in water, non-toxic and odorless. The post-treatment is simple and conforms to the principles of green chemistry.
· Mild conditions: The reaction can usually occur at room temperature or with a slight heating, making it suitable for compounds that are unstable to heat.
· Good selectivity: It causes less interference to other functional groups in the substrate (such as hydroxyl groups, phenolic hydroxyl groups).
· Low allergenicity: Its by-products are not as difficult to remove as those of DCC (DCU), and are less likely to cause allergies, giving it an advantage in the pharmaceutical industry.
5. Safety and Storage
· Irritation: This compound is irritating to the eyes, skin and respiratory tract. Appropriate personal protective equipment (such as gloves, goggles and laboratory coats) should be worn during operation.
· Moisture resistance: It must be stored in a sealed container in a dry environment to prevent decomposition due to contact with moisture in the air.
· Inert atmosphere: It is recommended to conduct weighing and feeding under an inert gas atmosphere to maintain its optimal reactivity.
Summary

CAS 1242336-77-1 (2-Chloro-1,3-dimethylchloromethylimidazoline, DMC) is an efficient condensing agent highly regarded in modern organic synthesis, particularly in drug development and fine chemical fields. It has replaced traditional condensing agents in many scenarios due to its mild reaction conditions, excellent selectivity, simple post-treatment, and environmentally friendly characteristics, and has become one of the preferred reagents for key reactions such as the synthesis of amide bonds.