N-Bromosuccinimide CAS 128-08-5

N-Bromosuccinimide CAS 128-08-5

n-bromosuccinimide CAS 128-08-5, n-bromosuccinimide, CAS 128-08-5

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Judging from the reaction conditions, it is in a moderate state. Neither does it require extremely harsh conditions like some reactions, such as extremely high temperatures, super strong pressures or extremely special environments, making the experimental operation extremely difficult and demanding extremely high equipment requirements; Nor will it be too mild to make the reaction difficult to proceed effectively.

128-08-5

C4H4BrNO2

177.98

204-877-2

N-Bromosuccinimide CAS 128-08-5 Inffromation


Chemical Name

N-Bromosuccinimide

Other Name

NBS; Bromosuccinimide; 2,5-PYRROLIDINEDIONE, 1-BROMO-; 1-BROMO-2,5-PYRROLIDINEDIONE

CAS

128-08-5

EINECS

204-877-2

Type

Pharmaceuticals, pesticides, synthetic material intermediates; Daily chemicals; Pharmaceutical raw materials; Organic raw materials

Molecular Formula

C4H4BrNO2

Molecular Weight

177.98



N-Bromosuccinimide CAS 128-08-5 Properties


Melting point 

175-180 °C (dec.)(lit.)

Boiling point 

221.4°C (rough estimate)

density 

2.098

vapor pressure 

14.8 hPa (20 °C)

refractive index 

1.6060 (estimate)

storage temp. 

Store at +2°C to +8°C.

solubility 

14.8g/l (decomposition)

pka

-2.78±0.20(Predicted)

form 

Crystalline Powder

color 

White to light yellow

Odor

characteristic odour of bromine

Water Solubility 

Soluble in acetone, tetrahydrofuran, dimethyl formamide, dimethyl sulfoxide and acetonitrile. Slightly soluble in water and acetic acid. Insoluble in ether, hexane and carbon tetrachloride.

Sensitive 

Moisture Sensitive


What is N-Bromosuccinimide?



In the vast and complex chemical field of organic synthesis, N-bromosuccinimide (NBS) is undoubtedly a representative brominated substance that occupies an important position. The bromination reaction involved has demonstrated many remarkable advantages.


Judging from the reaction conditions, it is in a moderate state. Neither does it require extremely harsh conditions like some reactions, such as extremely high temperatures, super strong pressures or extremely special environments, making the experimental operation extremely difficult and demanding extremely high equipment requirements; Nor will it be too mild to make the reaction difficult to proceed effectively. This moderate reaction condition provides great convenience for chemists in the actual operation process, making the reaction easier to control and operate, and reducing various problems that may arise due to the difficulty in controlling the conditions.


In terms of selectivity, the bromination reaction of N-bromosuccinimide performed quite well. It can precisely identify and act on specific chemical bonds or functional groups, just like a highly skilled craftsman who can accurately process the target area without causing unnecessary influence on other unrelated parts. This excellent selectivity enables efficient and accurate bromination reactions to be achieved even in complex organic molecular systems, significantly enhancing the synthesis efficiency and the purity of the products.


Yield is also one of the important indicators to measure the quality of a chemical reaction, and the bromination reaction of N-bromosuccinimide also performs well in this aspect. Under appropriate reaction conditions, it can be transformed into the target product in a relatively high proportion. This means that with the same raw material input, more expected products can be obtained, which not only reduces production costs but also minimizes the environmental pressure that may be caused by the handling of unreacted raw materials.


In addition, the product generated by this bromination reaction also has the characteristic of being easily cracked. This characteristic provides more possibilities and conveniences for subsequent chemical transformations. In organic synthesis, sometimes it is necessary to further modify and transform the intermediate products. The characteristic that the products are easy to decompose makes this process smoother and enables the target molecules to be gradually constructed according to the preset synthetic route.


The application scope of N-bromosuccinimide is very wide. In terms of the bromination of allyl and phenyl groups, it can achieve full radical bromination. During this process, the generation and reaction mechanism of free radicals enable bromine atoms to accurately add to specific positions, providing a basis for subsequent molecular structure modification and functionalization.


For ketones, aromatic compounds or heterocyclic compounds, N-bromosuccinimide can trigger electrophilic bromination reactions. In this type of reaction, it acts as an electrophilic reagent and can interact with the electron-rich regions of the substrate, introducing bromine atoms into the molecular structure, thereby altering the electron distribution and chemical properties of the molecule, providing an effective approach for the synthesis of organic compounds with specific functions.


In the addition reaction of alkenes, N-bromosuccinimide also plays an important role. It can undergo specific addition reactions with alkenes, forming new chemical bonds, expanding the chemical transformation methods of alkene compounds, and providing rich means for structural construction in organic synthesis.


In addition to its application in bromination reactions, N-bromosuccinimide is also commonly used as a stimulant and oxidant. In some specific chemical reaction systems, it can stimulate the reaction to proceed, enhance the activity and efficiency of the reaction, or change the chemical state of the substrate through oxidation to achieve specific chemical transformations.


Meanwhile, N-bromosuccinimide is also a commonly used brominating reagent in the chemical and pharmaceutical industries. In the chemical industry, it is widely used in the synthesis and modification of various organic compounds, providing a crucial bromination step for the production of chemical products with specific properties. In the pharmaceutical industry, it is an indispensable and important tool. The synthesis of many drug molecules is inseparable from bromination reactions. N-bromosuccinimide, with its excellent reactive performance, can precisely introduce bromine atoms into specific positions of drug molecules, thereby regulating the activity, stability and other pharmacological properties of drugs, providing strong support for the development of new drugs and the improvement of the production process of existing drugs.


As an important intermediate, N-bromosuccinimide has extensive applications in fields such as medicine, pesticides and natural polymer products. In the field of medicine, it is a key intermediate in numerous drug synthesis routes. By participating in various chemical reactions, it gradually constructs complex drug molecular structures. In the field of pesticides, it is also used to synthesize pesticide molecules with specific insecticidal, fungicidal or herbicidal activities, providing effective guarantees for agricultural production. For natural polymer products, N-bromosuccinimide can modify and functionalize them, endowing them with new properties and applications.


Due to its wide application and important role in multiple fields, the market prospect of N-bromosuccinimide is very broad. It plays an irreplaceable role in the markets of chemical engineering, pharmaceuticals and organic polymer materials. With the continuous development of these industries and technological progress, the demand for N-bromosuccinimide is also continuously increasing, providing a strong impetus for its market development.


From the perspective of chemical structure, N-bromosuccinimide is a 5-membered cyclic dicarboxylimide compound with a bromine substituent on the nitrogen atom. This unique structure endows it with special chemical properties and reactivity.


Since its discovery, N-bromosuccinimide (NBS) has been widely used in the bromination and oxidation reactions of several organic compounds. Initially, this important compound was proposed and studied by Ziegler and his colleagues. Their pioneering work laid the foundation for the later wide application and development of N-bromosuccinimide.


N-bromosuccinimide is a type of bromosuccinimide and plays an important role in organic synthesis. It is mainly used as a chemical reagent for free radical substitution and in electrophilic addition reactions. In free radical substitution reactions, it can generate free radical species that react with the substrate to achieve the substitution of bromine atoms at specific positions. In electrophilic addition reactions, it acts as an electrophilic reagent and can interact with the nucleophilic center in the substrate, adding bromine atoms to the molecular structure, thereby altering the properties and functions of the molecule.


In practical organic synthesis applications, N-bromosuccinimide (NBS) is typically used for the extreme bromination of allyl and phenyl groups. Under such extreme conditions, it can achieve efficient bromination reactions, providing a crucial step for the synthesis of organic compounds with specific structures and properties.


For ketones, aromatic substances or heterocyclic compounds, N-bromosuccinimide can trigger electrophilic bromination reactions. During this process, it can selectively react with specific parts of the substrate, introducing bromine atoms into the molecular structure, thereby achieving functional modification of these compounds.


In addition, N-bromosuccinimide can also promote the hydroxylation reaction, etherification reaction and endoesterification reaction of alkenes. In the hydroxylation reaction, it can guide the introduction of hydroxyl groups, altering the chemical properties and reactivity of alkenes. In the etherification reaction, it participates in the formation of ether bonds and builds new molecular structures. In the internal esterification reaction, it helps to form the lactone ring, providing an effective approach for the synthesis of compounds with specific cyclic structures.



N-Bromosuccinimide Uses


In today's complex and diverse field of the chemical industry, N-bromosuccinimide, as a crucial chemical substance, plays an indispensable role. It is not only a key intermediate in the production process of pharmaceuticals, pesticides and organic polymer products, but also has demonstrated remarkable application value in many fields due to its unique chemical properties and wide applicability. It has extremely wide uses and a market customer group with huge potential.


In the field of chemical engineering, N-bromosuccinimide is like a brilliant pearl, radiating a unique radiance. It is an extremely important organic synthesis resource and plays a key role in regulating low-energy bromination reactions. By ingeniously applying it, the reaction process can be precisely controlled, enabling the chemical reaction to proceed smoothly in the expected direction and laying a solid foundation for the synthesis of numerous chemical products. Meanwhile, in the production of rubber additives, N-bromosuccinimide is also an indispensable and important component. It can endow rubber products with specific properties, improve the quality and service life of rubber, and meet the diverse demands of different industries for rubber materials. In addition, in the production process of drugs, it also plays an important role, providing strong support for the research and development and production of drugs, and helping the pharmaceutical industry to keep moving forward. It is worth mentioning that it can also be used to produce bromoacetonitrile drugs, which play an important role in the prevention, treatment and management of diseases in certain specific fields. Not only that, in the chemical industry, N-bromosuccinimide is also widely used in the manufacturing process of thiabendazole. Thiabendazole, as an important chemical substance, has extensive applications in multiple fields, and the participation of N-bromosuccinimide ensures the efficiency and stability of its production process. In addition, it can also be used as a fruit chemical, playing a positive role in the preservation, anti-corrosion and quality improvement of fruits. Meanwhile, as one of the representative substances of disinfectants and antifungi, N-bromosuccinimide has also made significant contributions to ensuring the hygiene and health of people's living environment.


In the field of pharmaceuticals, N-bromosuccinimide reagents have demonstrated their outstanding performance even more. In organic reactions, its application is very typical and extensive. For example, in the bromination reactions of allyl, phenyl and carbonyl groups, the N-bromosuccinimide reagent can play a unique role, achieving precise bromination operations and providing a crucial step for the synthesis of drug molecules. With the continuous deepening and exploration of scientific research, people have gradually lifted more mysterious veils of N-bromosuccinimide and discovered that in addition to its outstanding performance in the above-mentioned traditional fields, it can also be widely applied in many other aspects such as stimulants and oxidants. This discovery undoubtedly opens up a broader space for its application in the pharmaceutical field and provides more possibilities for the research and development and innovation of new drugs.


In the field of natural polymer materials, N-bromosuccinimide also plays an irreplaceable and important role. It is a multifunctional brominating agent and performs well in the oxidation process of tryptophan. When reacting with other substances, it can selectively oxidize tryptophan. Although tyrosine, histidine and methionine residues may also be oxidized to a small extent, the overall specificity and effectiveness of the reaction can still be guaranteed. In addition, it can also be used to adjust the thiol groups of ribosomes, which is of great significance for in-depth research on the structure and function of ribosomes as well as related biological processes. Meanwhile, as a universal brominating agent, in the presence of AIBN (azo diisobutyl nitrile), N-bromosuccinimide can oxidize silyl ethers to aldehydes. This reaction has significant application value in organic synthesis and provides an effective method for the synthesis of compounds with specific structures.


From the perspective of the preparation method, N-bromosuccinimide can be elaborately prepared by reacting a cold sodium hydroxide solution of succinimide with an equal molar amount of bromine. This preparation method has been verified through long-term research and practice, and it has high feasibility and stability, which can ensure the acquisition of high-quality N-bromosuccinimide products.


In terms of practical applications, N-bromosuccinimide is mainly used as an additive in natural synthesis and rubber products. During the natural synthesis process, it can participate in complex chemical reactions, helping to construct natural product molecules with specific structures and functions, and providing an important tool for the synthesis and research of natural products. In rubber products, as an additive, it can improve the performance of rubber, enhance its strength, wear resistance and aging resistance, and make rubber products more in line with the demands of different application scenarios. Meanwhile, it is also a dedicated brominating agent for the laboratory preparation of allyl bromoalkenes and holds an important position in the scientific research and teaching of organic chemistry. By using N-bromosuccinimide, researchers can prepare allyl bromoalkenes more accurately and efficiently, providing a basis for further research and exploration. In addition, it is also a reagent for identifying primary alcohols, diols and tertiary alcohols, playing a significant role in the field of analytical chemistry. It can help researchers quickly and accurately identify different types of alcohol substances, providing strong support for chemical research and applications.


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