N-Bromosuccinimide

• Catalog No.: A15922
• CAS Number: 128-08-5
• M. F.: C4H4BrNO2
• M. W.: 177.98406
• Purity: 99%

SYNONYMS

• Title: N-溴丁二酰胺
• IUPAC name: 1-bromopyrrolidine-2,5-dione
• IUPAC Traditional name: N-bromosuccinimide
• Synonyms: NBS

DATABASE IDS

• Beilstein Number: 113916
• Merck Index: 141438
• CAS Number: 128-08-5
• EC Number: 204-877-2
• MDL Number: MFCD00005510

PROPERTIES

• Purity: 99%
• Density: 2.098
• Melting Point: 175-180°C dec.
• GHS Hazard statements: H301-H314-H318
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 22-34
• Safety Statements: 26-36/37/39-45
• Storage Warning: Light Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: III

REFERENCES

• Source of free-radical or positive bromine. For examples of radical benzylic bromination (Wohl-Ziegler), see: Org. Synth. Coll., 4, 921 (1963); 5, 145, 329, 825 (1973). The use of the ozone depleting solvent CCl₄ has been avoided by the use of the ionic liquid 1-n-Butyl-3-methylimidazolium hexafluorophosphate, L19086: Synlett, 702 (2003). Cleavage of carbohydrate benzyl ethers: J. Org. Chem., 55, 378 (1990), and of benzyl esters: Synlett, 219 (1994), occur under mild conditions; the benzyl group is converted to benzaldehyde. For allylic bromination, see e.g.: Org. Synth. Coll., 4, 108 (1963);.9, 112, 191 (1998) review: Chem. Rev., 43, 271 (1948).
• In the presence of a phosphine or phosphite, converts alcohols to alkyl bromides with inversion: Tetrahedron Lett., 3937 (1973). For a review of this and related reactions, see: Org. React., 29, 1 (1983).
• Alkenes undergo trans-addition reactions with NBS in combination with a nucleophile. For examples, see: Org. Synth. Coll., 6, 184, 560 (1988). With alcohols, bromohydrin ethers are formed. For use in the synthesis of cyclopropenone, see: Org. Synth. Coll., 6, 361 (1988):
  
• In the presence of DBU in MeOH, amides rearrange to amines in good yields, providing a mild and efficient alternative to the classical Hofmann halogen/ caustic alkali conditions: J. Org. Chem., 62, 7495 (1997).
• Sulfides to sulfoxides: J. Org. Chem., 37, 3976 (1968). Oximes to nitrile oxides: J. Org. Chem., 37, 436 (1968). Secondary alcohol in the presence of primary: Tetrahedron Lett., 2745 (1979). (In DMSO): Alkynes to ɑ-diketones: Can. J. Chem., 49, 1099 (1979).
• (Free radical): Aldehydes to acyl bromides or amides: Tetrahedron Lett., 31, 7237 (1990). Benzyl silyl ethers to aldehydes: Synlett, 345 (1990). Aldehydes to esters: Synlett, 347 (1990).
• For a brief feature on uses in synthesis, see: Synlett, 498 (2006). See also 1,3-Dibromo-5,5-dimethylhydantoin, A15510.
• For free-radical ɑ-bromination of a Boc glycine ester, see: Org. Synth. Coll., 9, 526 (1998).
• Both aliphatic and aromatic aldehydes are converted to acyl bromides under free-radical conditions: Tetrahedron Lett., 3809 (1979); Synlett, 347 (1990); Tetrahedron Lett., 31, 7237 (1990).
• In acetonitrile, NBS is a mild and regiospecific nuclear brominating agent for activated aromatics such as methoxybenzenes and naphthalenes: J. Org. Chem., 60, 5328 (1995). Deactivated aromatics, e.g. nitroarenes and benzotrifluorides, can be m-brominated under mild conditions in good yield with NBS in TFA, in the presence of H₂SO₄: Synlett, 1245 (1999).
• Examples of the use of NBS as a mild, selective oxidizing agent:
• For use as a mild catalyst in acetalization reactions, see Triethyl orthoformate, A13587.