N-Bromosuccinimide CAS 128-08-5


Free Sample N-Bromosuccinimide CAS 128-08-5
- Appearance:Powder
- Purity:99.8%
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Name: N-Bromosuccinimide
CAS: 128-08-5
MOQ: 1KG
Directory Guidance on N-Bromosuccinimide
Chemical Structure
Basic Info:
Melting point | 175-180 °C (dec.)(lit.) |
Boiling point | 221.4°C (rough estimate) |
bulk density | 750kg/m3 |
density | 2.098 |
vapor pressure | 14.8 hPa (20 °C) |
Product Introduction:
N-Bromosuccinimide (NBS for short) is a compound that plays an important role in the field of organic synthesis. Its chemical formula is C4H4BrNO2, its molecular weight is 177.98, and its CAS number is 128-08-5. In appearance, NBS usually appears as a white to milky crystalline solid or powder with a slight bromine odor, a melting point between 175℃-180℃, and a boiling point of 221.4℃. NBS has good solubility in a variety of organic solvents, such as acetone, tetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide, and acetonitrile, but has low solubility in water and acetic acid, and is insoluble in ether, hexane, and carbon tetrachloride.
There are two main methods for preparing N-Bromosuccinimide. One is to dissolve succinimide in a solution prepared with sodium hydroxide, crushed ice, and water, add liquid bromine in an ice-water bath, and after the reaction is completed, wash with ice water to remove excess bromine, and dry to obtain the product. Another method is to prepare it by reacting succinimide with NaBrO2 in the presence of HBr. These two methods have their own advantages and disadvantages. The former is relatively simple to operate, but the product quality is uneven, the utilization rate of bromine resources is low, and the production cost is high; the latter can obtain relatively pure products, but the reaction conditions are more complicated.
N-Bromosuccinimide has unique chemical properties. The bromine substituent on its nitrogen atom enables it to provide bromide ions in the reaction, thereby realizing the bromination reaction of organic compounds. This characteristic makes NBS play an irreplaceable role in organic synthesis. It is widely used in bromination reactions of allylic hydrogen, benzyl hydrogen, carbonyl α-position hydrogen and other special positions. It can also be used as a catalyst, oxidant and polymerization initiator.
Nature and Specifications:
Item | Specification |
Product Name | N-Bromosuccinimide |
CAS No. | 128-08-5 |
Appearance | Powder |
Shelf Life | 2 years |
Packing | As your requirements |
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 |
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- Route of synthesis (ROS)
- Method of Aanlysis (MOA)
- Nuclear Magnetic Resonance (NMR)
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N-Bromosuccinimide is an invaluable chemical used widely in organic synthesis. One of its more well-known applications is the allylic bromination reaction, where bromine atoms are introduced into olefin molecules via free radical mechanism at their allylic positions. This reaction can be used for synthesizing natural products, creating drug intermediates and altering polymeric materials. Synthesis of certain terpenoids requires building specific structures via multiple bromination-elimination steps; N-Bromosuccinimide’s superior selectivity ensures this. NBS can also be utilized for the bromination of aromatic rings with high electron cloud density (such as phenol and aniline derivatives). NBS’s superior regioselectivity helps avoid issues associated with oversubstitution caused by traditional bromination reagents.
N-Bromosuccinimide plays an essential role in polymer chemistry as both an initiator and modifier for polymerization reactions, often as free radical polymerization’s initiating agent or modifier. When used with peroxide as part of free radical polymerization reactions, NBS helps control chain initiation rate while modulating the molecular weight distribution of polymers produced. NBS may also be used for functional modifications of polyolefins such as adding bromine atoms into segments to increase flame retardant properties or act as active sites for subsequent grafting reactions; such modified materials find widespread applications throughout electronics packaging, automotive parts production industries as well as many other areas with growing market demands for such modified materials.
N-Bromosuccinimide can also play an essential role in drug development. Many drug molecules require bromine atoms to introduce specific pharmacophores or regulate metabolic stability; due to its mild reaction conditions and low toxicity byproducts, NBS makes an ideal choice for the synthesis of drug intermediates due to its mild reaction conditions and low toxicity byproducts. Antitumor drugs for instance often call for brominating specific parts of an indole or quinoline skeleton, where brominating NBS can significantly increase efficiency; additionally NBS can also be used in bromination of carbohydrate compounds to provide key intermediates needed in creating or altering glycosidic bonds in construction or modification projects.
N-Bromosuccinimide as a derivatization reagent has recently garnered greater consideration within analytical chemistry. By employing bromination reactions, NBS can transform hard-to-detect compounds into derivatives with specific absorption or fluorescence properties, thus increasing analytical sensitivity. N-Bromosuccinimide can also be used in environmental pollution detection to produce brominated derivatives of polycyclic aromatic hydrocarbons that increase mass spectrometry signal intensity for trace analysis. Furthermore, N-Bromosuccinimide may be useful in protein or nucleic acid labeling research by binding bromine atoms to biological macromolecules to investigate relationships between structure and function.
N-Bromosuccinimide stands out as an efficient and selective bromination reagent due to its solid state characteristics that facilitate accurate measurement compared with liquid bromination reagents such as bromine or hydrobromic acid, eliminating volatilization losses and operating risks caused by volatilized liquid solutions. NBS also features controllable bromine release rates that can adapt to suit different reaction systems.
Stability and safety are also among the primary advantages of N-Bromosuccinimide. It can be stored at room temperature without risk of decomposition for extended periods without decomposing, providing it is protected from light and moisture to preserve its activity. Liquid bromine must be kept tightly sealed under adverse storage conditions; while hydrobromic acid presents strong corrosive qualities and an offensive smell. NBS stands out as an ideal candidate for industrial scale-up production due to its low volatility and toxicity levels, meeting modern chemical industry’s safety and environmental protection standards. Furthermore, its primary reaction by-product – succinimide – is highly water soluble and easy to separate thus further decreasing post-processing costs.
From an economic viewpoint, N-Bromosuccinimide offers significant comprehensive cost-effectiveness. Although its unit price may be higher than bromine’s, its high reaction efficiency and low loss rate allow significant dosage reduction; for instance in some bromination reactions where NBS was used only 50%-70% of bromine dosage while reaction times were cut by over 30%. Furthermore, its easy handling of by-products reduces waste liquid treatment costs significantly while its high selectivity reduces raw material waste caused by side reactions; all these advantages translate to substantial economic benefits in large scale production settings.
The optimization of environmental performance is an important development direction of N-Bromosuccinimide in recent years. With the strict control of the emission of bromine compounds in various countries, the low residue characteristics of NBS are favored. The utilization rate of bromine in the reaction system can reach more than 90%, which is much higher than 60%-70% of bromine. In addition, the combination of NBS and green oxidants (such as hydrogen peroxide) can further reduce the formation of harmful by-products, which conforms to the atomic economy principle of green chemistry.
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Related References:
chemicalbook-N-Bromosuccinimide
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