N-Bromosuccinimide

Product Details

CasNo： 128-08-5

MF： C4H4BrNO2

Appearance： White to off-white crystal

Delivery Time： 15 days

Packing： 25kg/drum

Purity： 99%

1. Basic Information

• CAS Number: 128 - 08 - 5

• Molecular Formula: C4H4BrNO2

• Molecular Weight: 177.98 g/mol

• Synonyms: N - Bromosuccinimide (NBS), 1 - Bromo - 2,5 - pyrrolidinedione, Bromosuccinimide

2. Physical Properties

• Appearance: White to off - white crystalline powder or granular solid. It has a slightly characteristic odor of bromine.

• Density: Approximately 2.098 g/cm³.

• Melting Point: In the range of 173 - 175 °C, with decomposition starting around 182 °C.

• Solubility: Soluble in organic solvents such as acetone, tetrahydrofuran (THF), N,N - dimethylformamide (DMF), dimethyl sulfoxide (DMSO), and acetonitrile. It is slightly soluble in water and acetic acid, and insoluble in ether, hexane, and carbon tetrachloride.

3. Product Specifications

• Purity: Usually ≥ 99%. High - purity NBS is crucial for applications in fields like pharmaceuticals and fine chemicals, where impurities can significantly affect reaction outcomes.

• Active Bromine Content: ≥ 44%. This is an important parameter as it determines the brominating ability of the compound in various reactions.

• Chloride Content: ≤ 0.05%. Low chloride content is required to avoid interference in reactions sensitive to chloride ions.

• Loss on Drying: ≤ 0.5%. This indicates the amount of moisture present in the product, and low moisture content is essential for maintaining the stability and reactivity of NBS.?

4. Applications

• Bromination Reagent

• Allylic and Benzylic Bromination: NBS is widely used for the bromination of allylic and benzylic positions in organic compounds. For example, in the synthesis of allyl bromides from alkenes, NBS selectively replaces the allylic hydrogen atom. In the presence of a radical initiator like benzoyl peroxide, the reaction proceeds through a radical mechanism.?

• Free - Radical Bromination: It serves as a source of bromine radicals in low - energy bromination reactions. The bromine radical generated from NBS can react with substrates to form brominated products. It can also be used in the bromination of aromatic compounds under certain conditions, such as in the presence of a catalyst or under specific reaction conditions to achieve electrophilic aromatic bromination.

• Oxidizing Agent

• Oxidation of Alcohols: NBS can oxidize secondary alcohols to ketones. The reaction mechanism involves the formation of an intermediate that is then oxidized to the carbonyl compound. It can also be used in the oxidation of aldehydes to carboxylic acids. For instance, in some synthetic routes, NBS can be used to convert aldehydes into their corresponding bromo - substituted carboxylic acids.?

• Modification of Biomolecules: In biochemistry, NBS is used for the oxidation of certain amino acid residues. For example, it can be used in the oxidation of tryptophan residues in proteins, which can be useful for studying protein structure - function relationships or for chemical modification of proteins.?

• Pharmaceutical Intermediate?

• Antibiotic Synthesis: NBS is used in the synthesis of antibiotics such as cefaloram (benzyl cephalosporin). Its ability to introduce bromine atoms at specific positions in organic molecules is crucial for constructing the molecular framework required for the antibiotic's activity.?

• Anti - inflammatory and Anticancer Drug Synthesis: It plays a role in the synthesis of anti - inflammatory and anticancer drugs. The bromine - containing moieties introduced by NBS can be further modified and incorporated into the final drug molecules to enhance their biological activities, such as improving their binding affinity to specific receptors or enzymes.?

• Agricultural and Preservation Applications?

• Pesticide Synthesis: In the agricultural industry, NBS is used in the synthesis of pesticides like thiabendazole. The bromination step using NBS is an important part of the multi - step synthesis process of this pesticide, which is used to control fungal diseases in crops.?

• Fruit Preservation: It can be used as a fruit preservative and antifungal agent. NBS may act by inhibiting the growth of microorganisms on the surface of fruits, thus extending their shelf life.?

• Rubber Industry?

• As a Rubber Additive: NBS can be used as an additive in the rubber industry. It can participate in reactions that modify the rubber's molecular structure, for example, by introducing bromine atoms, which can improve the rubber's properties such as its resistance to heat, wear, and aging. It can also be used in the cross - linking process of certain types of rubbers to enhance their mechanical strength.?

5. Storage Conditions?

NBS should be stored in a cool, dry, and well - ventilated area. It is sensitive to moisture, so it must be kept away from sources of humidity. Sealed containers are recommended to prevent exposure to air and moisture. The ideal storage temperature is between 2 - 8 °C.?

6. Safety Information?

• Hazardous Symbols: C (Corrosive), Xn (Harmful).?

• Hazard Statements:?

• Harmful if swallowed (H302). Ingestion of NBS can cause harm to the digestive system.?

• Causes skin burns and eye damage (H314). Direct contact with the skin or eyes can lead to severe irritation, burns, and potential long - term damage.?

• May cause an allergic skin reaction (H317). Some individuals may be sensitive to NBS and develop allergic reactions upon skin contact.?

• Causes serious eye irritation (H318). Even brief contact with the eyes can result in significant discomfort and irritation.?

• Safety Statements:?

• In case of contact with eyes, rinse immediately with plenty of water and seek medical advice (S26). Prompt and thorough eye irrigation is crucial to minimize damage.?

• Wear appropriate protective clothing, gloves, and eye/face protection (S36/37/39). This includes chemical - resistant gloves, safety goggles, and protective clothing to prevent skin and eye contact.?

• In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible) (S45). Quick medical attention is essential in case of exposure or ingestion.?

• UN Number: UN3261. This number is used for the transportation of hazardous substances, and NBS is classified as a corrosive solid during transportation.?