1-bromopyrrolidine-2,5-dione

• ChemBase ID: 91856
• Molecular Formular: C4H4BrNO2
• Molecular Mass: 177.98406
• Monoisotopic Mass: 176.94254037
• SMILES: N1(C(=O)CCC1=O)Br
• Canonical SMILES: BrN1C(=O)CCC1=O
• InChI: InChI=1S/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
• InChIKey: PCLIMKBDDGJMGD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-bromopyrrolidine-2,5-dione
• IUPAC Traditional name: N-bromosuccinimide
• Synonyms: 1-Bromopyrrolidine-2,5-dione; N-Bromosuccinimide; 1-Bromo-2,5-Pyrrolidinedione; Succinobromimide; NBS; 1-bromopyrrolidine-2,5-dione; Bromosuccinimide; NSC 16; Succinbromimide; N-Bromo succinimide; N-Bromosuccinimide; N-bromosuccinimide; N-溴琥珀酰亚胺; N-溴丁二酰胺

Database IDs

• CAS Number: 128-08-5
• EC Number: 204-877-2
• MDL Number: MFCD00005510
• Beilstein Number: 113916
• Merck Index: 141438
• PubChem SID: 24851059; 162078554; 24892048
• PubChem CID: 67184
• CHEBI ID: 53174
• Chemspider ID: 60528
• Wikipedia Title: N-Bromosuccinimide

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.08120419
• LogD (pH = 7.4): -0.08120419
• Log P: -0.08120419
• Molar Refractivity: 30.2166 cm^3
• Polarizability: 11.852916 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1.47 g / 100 mL (25°C) in water; Insoluble (25°C) in CCl4
• Apperance: White solid
• Melting Point: 175 - 178°C; 175-180 °C (dec.); 175-180 °C (dec.)(lit.); 175-180°C; 175-180°C dec.; 180-183°C
• Boiling Point: 339 °C
• Density: 2.098; 2.098 g/cm3 (solid); 2.098 g/ml

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: Corrosive/Harmful/Light Sensitive/Moisture Sensitive/Store under Argon/Keep Cold; Light Sensitive
• European Hazard Symbols: Corrosive (C); X
• UN Number: 1759; 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; III
• Australian Hazchem: 2X
• Risk Statements: 22-34; R:34
• Safety Statements: 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• Main Hazard: Irritant
• GHS Hazard statements: H301-H314-H318; H302-H314
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (RT); 95+%; 99%
• Grade: purum; ReagentPlus®
• Empirical Formula (Hill Notation): C4H4BrNO2

DETAILS

MP Biomedicals - 02101152

Crystalline
Allylic bromination reagent. Cleaves peptide at Tryptophyl residues. Decarboxylates α-amino acids, peptides, and proteins in aqueous solutions.

Sigma Aldrich - B81255

Application
Common brominating agent. Oxidizes silyl ethers to aldehydes in the presence of AIBN.1,2
Versatile brominating agent. For the oxidation of tryptophan though tyrosine, histidine and methionine residues may be oxidized to a lesser extent. Also used for the modification of ribosomal sulfhydryl groups.
Packaging
1, 5 kg in poly bottle
100, 500 g in poly bottle
5 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 18350

Application
Versatile brominating agent. For the oxidation of tryptophan though tyrosine, histidine and methionine residues may be oxidized to a lesser extent. Also used for the modification of ribosomal sulfhydryl groups.

Toronto Research Chemicals - B686995

N-Bromosuccinimide is a brominated succinimide used as a chemical reagent in radical substitution and electrophilic addition reactions in organic synthesis.

REFERENCES

• Alberola, A. et al.: Anal. Quim., 74, 761 (1968)
• Kobayashi, T. et al.: J. Chem. Soc. Perk. Trans., 12, 1372 (1968)
• Paulini, K. et al.: CHem. Ber., 127, 685 (1968)
• 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.