N-Bromosuccinimide CAS 128-08-5 NBS
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- Appearance: White powder
- Assay: 99. 0%min
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N-Bromosuccinimide: The Complete Guide
N-Bromosuccinimide for Sale
Basic Info of N-Bromosuccinimide
NBS; Bromosuccinimide; 2,5-PYRROLIDINEDIONE, 1-BROMO-; 1-BROMO-2,5-PYRROLIDINEDIONE
Pharmaceuticals, pesticides, synthetic material intermediates; Daily chemicals; Pharmaceutical raw materials; Organic raw materials
What is N-Bromosuccinimide?
N-bromosuccinimide (NBS) is an important brominating representative in organic synthesis. The bromination response has the advantages of moderate response conditions, excellent selectivity, high return and also easy splitting up of products. It is applied to the totally free radical bromination of allyl and also benzyl groups; Electrophilic bromination response of ketones, fragrant compounds or heterocyclic compounds and addition reaction of olefins; It is additionally commonly made use of as stimulant as well as oxidant, as well as is a commonly used bromination reagent in chemical and also pharmaceutical industries. As a crucial intermediate of medicine, pesticide and natural polymer products, N-bromosuccinimide is widely made use of and also has a wide market prospect. It plays an irreplaceable role in the chemical, pharmaceutical and also organic polymer materials markets.
N-bromosuccinimide is a 5 membered cyclic dicarboxyimide compound with a bromine substituent on the nitrogen atom. N-bromosuccinimide (NBS) has been commonly made use of in the Bromination and also oxidation of several organic compounds. Initially presented by Ziegler as well as his coworkers. N-bromosuccinimide is a kind of bromosuccinimide, which is made use of as a chemical reagent free of cost radical alternative and also electrophilic addition reaction in organic synthesis.
N-bromosuccinimide (NBS) is typically made use of in extreme bromination of allyl and also benzyl teams; Electrophilic bromination of ketones, fragrant substances or heterocyclic compounds; Hydroxylation of olefins, etherification response as well as lactonization reaction.
- As a vital intermediate of medication, pesticide as well as organic polymer product, N-bromosuccinimide has a vast array of uses and broad market potential customers, and has an irreplaceable role in the chemical, pharmaceutical, and natural polymer material sectors.
- Organic synthesis resources, used to regulate low-energy bromination reactions, as well as additionally utilized to generate rubber auxiliaries and pharmaceuticals. Can manufacture bromoacetonitrile medicine. In the chemical industry, it is made use of to manufacture thiabendazole, as well as it can also be used as a fruit chemical, in addition to a disinfectant and also antifungal representative.
- The typical use of N-bromosuccinimide reagents in organic responses is the bromination of allylic, benzylic, and carbonyl alpha hydrogens. With the growing of research, it is progressively located that NBS can additionally have lots of applications in numerous aspects such as stimulant and oxidant.
- Multifunctional brominating agent. Made use of in the oxidation of tryptophan, yet tyrosine, histidine and methionine residues may be oxidized to a lesser extent. It can likewise be made use of for adjustment of sulfhydryl groups of ribosomes. Universal brominating agent. Silyl ethers can be oxidized to aldehydes in the existence of AIBN.
- NBS can be prepared by responding an ice-cooled NaOH service of succinimide with equimolar bromine. It is mainly made use of in natural synthesis and also additives for rubber items. It is a special brominating agent for lab preparation of allyl brominated olefins, and is likewise a reagent for identifying main, second as well as tertiary alcohols.
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Application of N-Bromosuccinimide
N-Bromosuccinimide (NBS) is a mild bromination reagent, which is suitable for the bromination of allylic and benzylic positions. It not only has mild reaction conditions, convenient operation, but also has high reaction selectivity. Less response.
NBS can undergo benzene ring bromination reaction with aromatic ethers (such as anisole, m-anisole, α-naphthyl methyl ether, etc.). With a small amount of Friedel-Crafts reaction catalyst, such as aluminum trichloride, zinc chloride or iron, etc., benzene and toluene can also undergo benzene ring bromination reaction with NBS to obtain bromobenzene and p-bromotoluene, respectively.
The addition of N-bromosuccinimide to alkenes under acid catalysis is an important method for the preparation of β-halohydrin. The method has high stereoselectivity, high yield, pure product, mild reaction and convenient operation. The yield reached 82%. The reaction formula is as follows:
Dimethyl sulfoxide (DMSO) is a very effective solvent. Using NBS to react with alkenes in aqueous DMSO, a good and highly stereoselective addition product can be obtained with a yield of 92%. The reaction formula is:
NBS is a very good carbonyl α-bromination reagent, the reaction is easy to operate and widely used. In order to improve the rate and yield of the reaction, many corresponding catalytic systems have been developed. Rapid bromination of 1,3-dicarbonyl compounds by NBS catalyzed by Mg(ClO4)2. The reaction was carried out mildly in CH3CN or EtOAc. The reaction has good stereoselectivity, and can easily prepare α-bromo 1,3-dicarbonyl compounds which are very important in organic synthesis.
The traditional use of N-bromosuccinimide reagents in organic reactions is the bromination of allylic, benzylic, and carbonyl α-hydrogens. With the deepening of research, it is gradually found that NBS can also have many applications in many aspects such as catalyst and oxidant.
- NBS as a catalyst NBS is used as a catalyst, and toluenesulfonamide and alcohols are used as nucleophiles to react activated styrene under mild conditions to obtain the amino groups (yields60%～83%) and alkoxy groups of activated styrene, respectively. Derivatives (yields75%～85%). Both types of reactions are in high yields and 100% use Markov addition. Using NBS as a catalyst, the alcohol was acetylated with acetic anhydride, and the reaction was carried out with chloroform as a solvent at room temperature with high yield and few by-products.
- NBS as oxidant Many secondary alcohols are oxidized to ketones with NBS. The reaction uses a cobalt complex of acetylacetone as a catalyst.
- Application of NBS in polymer research Living polymerization is a very important method to prepare polymers with specific structure and narrow molecular weight distribution. Because the N-Br bond in NBS is very active, it is easy to be broken under heating to obtain active succinimide free radicals and bromine free radicals inert to free radical initiation. Therefore, it is also possible to use NBS as a chain-initiated transfer terminator for free-radical polymerization.
Preparation of N-Bromosuccinimide
- The alkali solution reaction of bromine and succinimide, the product quality of gained is uneven, the utilization rate of bromine resources is low, and the production cost is high; Concrete experimental steps: Succinimide is dissolved in sodium hydroxide, crushed To the solution prepared by ice and water, liquid bromine was added under the condition of ice-water bath. After the reaction, the crude product was washed with ice water to remove residual bromine, and dried to obtain the product N-bromosuccinimide. Purity: 90%～97%. mp: 173～175℃, 180～183℃ (decomposition), the reaction formula is as follows:
- Reacting with sodium bromate, hydrobromic acid and succinimide, hydrobromic acid has high volatility and serious pollution, and the concentration of domestic hydrobromic acid is different, and the production process is not easy to control.
- The technique of synthesizing N-bromosuccinimide with succinimide, sodium bromate, sodium bromide and sulfuric acid, but there is no specific operation process, nor specific raw material proportioning and feeding order, and The feeding amount is at the milligram level, which cannot provide a reliable reference for industrial production.
- The experimental steps of synthesizing N-bromosuccinimide with sodium bromate, sodium bromide, sulfuric acid and succinimide as main raw materials: Under the condition of stirring at 25°C, 17.8g (180mmol) Succinimide and 10.4g (69mmol) of sodium bromate were dissolved in 60mL of water, 6.6mL of sulfuric acid and 14.2g (138mmol) of sodium bromide solution were added dropwise. After the addition, the reaction was stirred for 2.5h, filtered and dried to obtain 27.9g of N -Bromosuccinimide, yield 87%.
- N-Bromosuccinimide – PubChem
- What is N-Bromosuccinimide? – ChemicalBook
- Wu Jing, Pei Wen.Research progress of N-bromosuccinimide in organic reactions[J].Guangzhou Chemical Industry,2011,39(09):31-34.