128-08-5
CHEMICAL AND PHYSICAL PROPERTIES
| Physical Description | Solid with a mild odor of bromine; [Merck Index] White, pale yellow, or cream-colored powder; [Alfa Aesar MSDS] |
|---|---|
| Color/Form | Orthorhombic bisphenoidal crystals |
| Odor | Faint odor of bromine |
| Boiling Point | 338.9 °C at 101.325 kPa |
| Melting Point | 173-175 °C (slight decomposition) |
| Solubility | In water, 1.47 g/100 g water at 25 °C |
| Density | 2.098 g/cu cm at 25 °C |
| Vapor Pressure | 11.0 [mmHg] |
| Stability/Shelf Life | Stable under recommended storage conditions. |
| Decomposition | Melting range 172-178 °C (decomposes). |
| Chemical Classes | Nitrogen Compounds -> Succinimides |
SAFETY INFORMATION
| Signal word | Warning |
|---|---|
| Pictogram(s) |
 Flame Over Circle Oxidizers GHS03  Corrosion Corrosives GHS05  Exclamation Mark Irritant GHS07  Health Hazard GHS08  Environment GHS09 |
| GHS Hazard Statements |
H272:Oxidising liquids;Oxidising solids H290:Corrosive to Metals H315:Skin corrosion/irritation H317:Sensitisation, Skin H319:Serious eye damage/eye irritation H341:Germ cell mutagenicity H400:Hazardous to the aquatic environment, acute hazard |
| Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P308+P313:IF exposed or concerned: Get medical advice/attention. |
COMPUTED DESCRIPTORS
| Molecular Weight | 177.98 g/mol |
|---|---|
| XLogP3 | -0.1 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Exact Mass | 176.94254 g/mol |
| Monoisotopic Mass | 176.94254 g/mol |
| Topological Polar Surface Area | 37.4 Ų |
| Heavy Atom Count | 8 |
| Formal Charge | 0 |
| Complexity | 129 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
PRODUCT INTRODUCTION
description
N-bromosuccinimide is a five-membered cyclic dicarboximide compound having a bromo substituent on the nitrogen atom. It has a role as a reagent. It is a dicarboximide, a pyrrolidinone and an organobromine compound. It is functionally related to a succinimide. N-Bromosuccinimide (NBS) is a organobromide compound used in a variety of bromination reactions for chemical synthesis. It can be used to donate bromine to alkenes, to allylic or benzyl compounds, to carbonyl-containing compounds as well as aromatic compounds such as phenols, anilines, and various aromatic heterocycles. NBS will decompose over time giving off bromine. Pure NBS is white, but it is often found to be off-white or brown colored by bromine. NBS can be used as a protein modification agent that targets tryptophan and histidine residues.
Preparation
NBS is commercially available and can also be synthesized in the laboratory. Sodium hydroxide and bromine are added to an ice-water solution of succinimide. The NBS product precipitates out and can be collected by filtration. Crude NBS gives better yield in the Wohl-Ziegler reaction. In other cases, impure NBS (slightly yellow-colored) may provide unreliable results. It can be purified by recrystallization from 90-95 °C water.