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N-Bromosuccinimide ( NBS ) 1-Bromopyrrolidine-2,5-dione | For Synthesis
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Description
N-Bromosuccinimide (NBS)
Other Names: NBS, Succinbromimide
CAS Number: 128-08-5
Sum Formula: C₄H₄BrNO₂
Molar Mass: 177.98 g/mol
Appearance: White to off-white crystalline powder
N-Bromosuccinimide is an organic brominating and oxidizing reagent commonly used in organic synthesis. It is especially valued for selective bromination of alkenes and aromatic compounds and for various oxidation reactions in research and industrial processes.
Chemical and Physical Properties
Density: ~2.098 g/cm³
Melting Point: 173–175°C (with decomposition)
Boiling Point: Decomposes before boiling
Solubility in Water: Slightly soluble
Solubility in Other Solvents: Soluble in acetone, DMF (dimethylformamide), and acetonitrile
Odor: Odorless to faint characteristic odor
Applications
Organic Synthesis: Used for allylic and benzylic bromination reactions.
Halogenation Reactions: Preferred for selective bromination under mild conditions.
Oxidizing Agent: Employed in various oxidation protocols for alcohols, amines, and sulfides.
Material Science: Studied for surface functionalization reactions involving bromination.
Pharmaceutical Chemistry: Applied in the preparation of intermediates for active compounds.
Safety
Signal Word: Danger
H272 (38.7%): May intensify fire; oxidizer [Danger Oxidizing liquids; Oxidizing solids]
H290 (38.7%): May be corrosive to metals [Warning Corrosive to Metals]
H302 (55.8%): Harmful if swallowed [Warning Acute toxicity, oral]
H314 (35.2%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H315 (46.2%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (21.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H319 (65.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (26.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H341 (15.1%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
H400 (43.2%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
P203, P210, P220, P234, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P370+P378, P390, P391, P403+P233, P405, P406, and P501
Handling and Storage
Storage Conditions: Store in a tightly closed container in a cool, dry, and well-ventilated place away from heat and light. Protect from moisture and incompatible materials such as strong reducing agents.
Handling Precautions: Handle under inert atmosphere if possible. Avoid exposure to moisture to prevent decomposition.