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Published TCIMAIL newest issue No.197
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CAS RN: 128-08-5 | Product Number: B0656
N-Bromosuccinimide
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Purity: >98.0%(T)
Synonyms:
- NBS
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 25G |
18,00 €
|
8 | ≥100 |
|
| 100G |
30,00 €
|
25 | ≥100 |
|
| 500G |
117,00 €
|
10 | ≥100 |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| 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 | 14.7 g/l 25 °C |
| Solubility (soluble in) | Acetone |
GHS
| Pictogram |
|
| Signal Word | Danger |
| Hazard Statements | H302 : Harmful if swallowed. H314 : Causes severe skin burns and eye damage. H290 : May be corrosive to metals. |
| Precautionary Statements | P260 : Do not breathe dust. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection. P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water. P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor. P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor. |
Related Laws:
| EC Number | 204-877-2 |
Transport Information:
| UN Number | UN3261 |
| Class | 8 |
| Packing Group | III |
| HS Number | 2925199590 |
Application
TCI Practical Example: Bromination Reaction Using N-Bromosuccinimide
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Used Chemicals
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Procedure
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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
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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
Articles/Brochures
TCIMAIL
[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
Product Documents (Note: Some products will not have analytical charts available.)
Safety Data Sheet (SDS)
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Specifications
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