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CAS RN: 128-08-5 | Product Number: B0656
N-Bromosuccinimide
×
Purity: >98.0%(T)
Synonyms:
- NBS
Product Documents:
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| Product Number | B0656 |
Purity / Analysis Method 
|
>98.0%(T) |
| Molecular Formula / Molecular Weight | C__4H__4BrNO__2 = 177.99 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature
|
Refrigerated (0-10°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Light Sensitive,Moisture Sensitive,Heat Sensitive |
| CAS RN | 128-08-5 |
| Reaxys Registry Number | 113916 |
| PubChem Substance ID | 87563662 |
| SDBS (AIST Spectral DB) | 1944 |
| Merck Index (14) | 1438 |
| MDL Number | MFCD00005510 |
Specifications
| Appearance | White to Orange to Green powder to crystal |
| Purity(Iodometric Titration) | min. 98.0 % |
Properties (reference)
| Melting Point | 176 °C(dec.) |
| Boiling Point | 339 °C |
| Solubility in water | Slightly soluble |
| Degree of solubility in water | 14.8 g/l 20 °C |
| Solubility (soluble in) | Acetone |
GHS
| Pictogram |
|
| Signal Word | Warning |
| Hazard Statements | H315 : Causes skin irritation. H319 : Causes serious eye irritation. H317 : May cause an allergic skin reaction. H410 : Very toxic to aquatic life with long lasting effects. H272 : May intensify fire; oxidizer. H290 : May be corrosive to metals. |
| Precautionary Statements | P501 : Dispose of contents/ container to an approved waste disposal plant. P261 : Avoid breathing dust. P273 : Avoid release to the environment. P272 : Contaminated work clothing should not be allowed out of the workplace. P220 : Keep away from clothing and other combustible materials. P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P234 : Keep only in original packaging. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection. P302 + P352 : IF ON SKIN: Wash with plenty of water. P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish. P390 : Absorb spillage to prevent material damage. P391 : Collect spillage. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P362 + P364 : Take off contaminated clothing and wash it before reuse. P333 + P313 : If skin irritation or rash occurs: Get medical advice/ attention. P406 : Store in a corrosion resistant container with a resistant inner liner. |
Related Laws:
Transport Information:
| UN Number | UN3085 |
| Class | 5.1 / 8 |
| Packing Group | III |
| H.S.code* | 2925.19-000 |
Application
TCI Practical Example: Bromination Reaction Using N-Bromosuccinimide
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Used Chemicals
-
Procedure
-
A solution of 2-methylbenzo[b]thiophene (500 mg, 3.4 mmol) in acetonitrile (5 mL) was stirred under nitrogen at 0 ˚C. Then NBS (630 mg, 3.5 mmol) was added the solution. The ice bath was removed and the mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with water and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the crude was purified by silica gel column chromatography (hexane, Rf = 0.65) to give 3-bromo-2-methylbenzo[b]thiophene as a white solid (759 mg, 99% yield).
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Experimenter’s Comments
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The reaction mixture was monitored by TLC (hexane, Rf = 0.65).
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Analytical Data
-
3-bromo-2-methylbenzo[b]thiophene
1H NMR (270 MHz, CDCl3); δ 7.70-7.75 (m, 2H), 7.30-7.44 (m, 2H), 2.56 (s, 3H).
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Lead Reference
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- Reactive ligand influence on initiation in phenylene catalyst-transfer polymerization
Application
A Method for the Synthesis of Acyclic Haloamines with Ring Opening of Cyclic Amines
Experimental procedure:
To a vial, Piv-protected amine (1 eq.), AgNO3 (4 eq.), (NH4)2S2O8 (4 eq.), and NCS or NBS (4 eq.) is added and dissolved in 1:9 acetone:water (0.2 M). The resulting mixture is stirred at room temperature. After 30 minutes, the reaction mixture is partitioned between EtOAc and H2O and separated. The aqueous layer is extracted with EtOAc in triplicate and the combined organic layers concentrated in vacuo. The crude mixture is then purified over silica column eluting with an EtOAc:Hex. Mixture to afford the desired haloamine product.
To a vial, Piv-protected amine (1 eq.), AgNO3 (4 eq.), (NH4)2S2O8 (4 eq.), and NCS or NBS (4 eq.) is added and dissolved in 1:9 acetone:water (0.2 M). The resulting mixture is stirred at room temperature. After 30 minutes, the reaction mixture is partitioned between EtOAc and H2O and separated. The aqueous layer is extracted with EtOAc in triplicate and the combined organic layers concentrated in vacuo. The crude mixture is then purified over silica column eluting with an EtOAc:Hex. Mixture to afford the desired haloamine product.
References
- Deconstructive diversification of cyclic amines
PubMed Literature
Documents
Product Articles
[Product Highlights] A Method for the Synthesis of Acyclic Haloamines with Ring Opening of Cyclic Amines[Research Articles] Carbon-Heteroatom Bond Formation at the Benzylic Position of Methylarenes
[TCI Practical Example] Bromination Reaction Using N-Bromosuccinimide
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Specifications
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