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128-08-5 molecular structure
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1-bromopyrrolidine-2,5-dione

ChemBase ID: 91856
Molecular Formular: C4H4BrNO2
Molecular Mass: 177.98406
Monoisotopic Mass: 176.94254037
SMILES and InChIs

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

Cite this record

CBID:91856 http://www.chembase.cn/molecule-91856.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -0.08120419  LogD (pH = 7.4) -0.08120419 
Log P -0.08120419  Molar Refractivity 30.2166 cm3
Polarizability 11.852916 Å3 Polar Surface Area 37.38 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
1.47 g / 100 mL (25°C) in water expand Show data source
Insoluble (25°C) in CCl4 expand Show data source
Apperance
White solid expand Show data source
Melting Point
175 - 178°C expand Show data source
175-180 °C (dec.) expand Show data source
175-180 °C (dec.)(lit.) expand Show data source
175-180°C expand Show data source
175-180°C dec. expand Show data source
180-183°C expand Show data source
Boiling Point
339 °C expand Show data source
Density
2.098 expand Show data source
2.098 g/cm3 (solid) expand Show data source
2.098 g/ml expand Show data source
Storage Condition
2-8°C, Desiccate expand Show data source
Storage Warning
Corrosive/Harmful/Light Sensitive/Moisture Sensitive/Store under Argon/Keep Cold expand Show data source
Light Sensitive expand Show data source
European Hazard Symbols
Corrosive Corrosive (C) expand Show data source
X expand Show data source
UN Number
1759 expand Show data source
3261 expand Show data source
UN3261 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
8 expand Show data source
Packing Group
2 expand Show data source
III expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
22-34 expand Show data source
R:34 expand Show data source
Safety Statements
26-36/37/39-45 expand Show data source
S:26-27/28-36/37/39-46-64 expand Show data source
EU Classification
C10 expand Show data source
EU Hazard Identification Number
8B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS06 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Danger expand Show data source
Main Hazard
Irritant expand Show data source
GHS Hazard statements
H301-H314-H318 expand Show data source
H302-H314 expand Show data source
GHS Precautionary statements
P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A expand Show data source
P280-P305 + P351 + P338-P310 expand Show data source
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 expand Show data source
RID/ADR
UN 3261 8/PG 2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥95.0% (RT) expand Show data source
95+% expand Show data source
99% expand Show data source
Grade
purum expand Show data source
ReagentPlus® expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C4H4BrNO2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02101152 external link
Crystalline
Allylic bromination reagent. Cleaves peptide at Tryptophyl residues. Decarboxylates α-amino acids, peptides, and proteins in aqueous solutions.
Sigma Aldrich - B81255 external link
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 external link
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 external link
N-Bromosuccinimide is a brominated succinimide used as a chemical reagent in radical substitution and electrophilic addition reactions in organic synthesis.

REFERENCES

REFERENCES

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  • • 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.
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