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N-Bromosuccinimide

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N-Bromosuccinimide Basic information
N-Bromosuccinimide Chemical 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.  0-6°C
  • solubility 14.8g/l (decomposition)
  • pka-2.78±0.20(Predicted)
  • form Crystalline Powder
  • color White to light yellow
  • Odorcharacteristic 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
  • Merck 14,1438
  • BRN 113916
  • Stability:Stable. Incompatible with strong oxidizing agents, halogenated hydrocarbons.
  • InChIKeyPCLIMKBDDGJMGD-UHFFFAOYSA-N
  • CAS DataBase Reference128-08-5(CAS DataBase Reference)
  • NIST Chemistry Reference2,5-Pyrrolidinedione, 1-bromo-(128-08-5)
  • EPA Substance Registry SystemN-Bromosuccinimide (128-08-5)
Safety Information
  • Hazard Codes C,Xn
  • Risk Statements 22-34-36/37/38
  • Safety Statements 26-36/37/39-45-37/39
  • RIDADR UN 3261 8/PG 2
  • WGK Germany 3
  • Hazard Note Harmful
  • TSCA Yes
  • HazardClass 8
  • PackingGroup III
  • HS Code 29251995
  • ToxicityLD50 orally in Rabbit: > 2000 mg/kg
MSDS
N-Bromosuccinimide Usage And Synthesis
  • Chemical Propertieswhite to light yellow crystalline powder
  • UsesN-Bromosuccinimide is a brominated succinimide used as a chemical reagent in radical substitution and electrophilic addition reactions in organic synthesis.
  • UsesNBS, is a chemical reagent used in organic chemistry in electrophilic addition reactions and radical substitution
  • UsesIn bromination of olefins; in oxidation of alcohols to aldehydes and ketones and of aldehydes to acid bromides.
  • DefinitionChEBI: A five-membered cyclic dicarboximide compound having a bromo substituent on the nitrogen atom.
  • PreparationN-Bromosuccinimide (NBS) is a widely used mild brominating agent and used as chemical intermediate and building block for several chemical production processes, especially in pharma related applications.
    Preparation of N-bromosuccinimide
    1.62mol (160g) succinimide is dissolved in a mixture of 1.60mol (64g) NaOH, 300g crushed ice and 400ml water. Cool the mixture in an ice bath, and add 85ml (1.65 mol, 264g) Br2 at once while stirring violently. Stir for two more minutes, then filter the precipitated product and wash with ice water. Dry in a desiccator. Yield 75-81%.
    Don't clean up NBS too much, the stinky yellow stuff still containing a bit of Br2 works best.
  • Safety ProfilePoison by intraperitoneal route. An irritating poison to skin, eyes, and mucous membranes. Reacts explosively with adme, dtallyl sulfide, and hydrazine hydrate. Explosive reaction with propiononitrile after heating to 105℃ for 24 hours. Violent reaction with dtbenzoyl peroxide + 4-tok acid. When heated to decomposition it emits toxic fumes of Brand NOx. See also BROMIDES and NITROGEN MONOXIDE.
  • Purification MethodsN-Bromosuccinimide (30g) is purified by dissolving rapidly in 300mL of boiling water and filtering through a fluted filter paper into a flask immersed in an ice bath, and left for 2hours. The crystals are filtered off, washed thoroughly with ca 100mL of ice-cold water and drained on a Büchner funnel before drying under vacuun over P2O5 or CaCl2 [Dauben & McCoy J Am Chem Soc 81 4863 1959]. This brominating agent has also been crystallised from acetic acid or water (10 parts), washed in water and dried in vacuo [Wilcox et al. J Am Chem Soc 108 7693 1986, Shell et al. J Am Chem Soc 108 121 1986, Phillips & Cohen J Am Chem Soc 108 2013 1986, Beilstein 21/9 V 543.]
N-Bromosuccinimide Preparation Products And Raw materials
N-Bromosuccinimide(128-08-5)Related Product Information
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