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CAS RN: 128-08-5 | Product Number: B0656

N-Bromosuccinimide


Purity: >98.0%(T)
Synonyms:
  • NBS
Documents:
25G
$26.00
4   8   ≥100 
100G
$45.00
6   3   ≥100 
500G
$135.00
5   5   ≥100 

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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 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 Pictogram 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 P501 : Dispose of contents/ container to an approved waste disposal plant.
P260 : Do not breathe dusts or mists.
P270 : Do not eat, drink or smoke when using this product.
P234 : Keep only in original container.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P390 : Absorb spillage to prevent material damage.
P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower.
P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P363 : Wash contaminated clothing before reuse.
P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth.
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.
P406 : Store in corrosive resistant container with a resistant inner liner.
P405 : Store locked up.
Related Laws:
Transport Information:
UN Number (DOT-AIR) UN3261
Class (DOT-AIR) 8
Packing Group (TCI-A) III
HS Number 2925.19.9100
Application
TCI Practical Example: Bromination Reaction Using N-Bromosuccinimide

TCI反応実例:N-ブロモスクシンイミドを用いたブロモ化反応

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).

Experimenter’s Comments

The reaction mixture was monitored by TLC (hexane, Rf = 0.65).

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).

Lead Reference


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.

References


PubMed Literature


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