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Product Code
BR1130
CAS
128-08-5

N-Bromosuccinimide

CAS 128-08-5 | Product Code BR1130
Synonyms 1-Bromopyrrolidine-2,5-dione, 1-Bromo-2,5-pyrrolidinedione, NBS
Pack size Price SKU UK Europe China
25 g £13.00 BR1130-25G In Stock (5+) In Stock (5+) In Stock (5+)
100 g £22.00 BR1130-100G In Stock (5+) Enquire In Stock (5+)
500 g £26.00 BR1130-500G In Stock (5+) Enquire In Stock (5+)
1 kg £38.00 BR1130-1KG In Stock (5+) In Stock (4.0) In Stock (5+)
5 kg £185.00 BR1130-5KG In Stock (1) Enquire Enquire
25 kg £550.00 BR1130-25KG In Stock (2) Enquire Enquire

Shipping times: UK Stock – Next Day | Germany Stock – 7-10 days | China Stock – 10-14 days

1

Details

2

Chemical Properties

3

Hazards

4

Transport

5

Documentation

6

Literature

Product Code

BR1130

CAS Number

128-08-5

IUPAC

1-bromopyrrolidine-2,5-dione

Canonical Smiles

O=C1CCC(=O)N1Br

InChI

InChI=1S/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2

InChI Key

PCLIMKBDDGJMGD-UHFFFAOYSA-N

MDL Number

MFCD00005510

EINECS Number

204-877-2

Molecular Formula

C4H4BrNO2

UNSPSC Code

12352005

SKU

BR1130

Synonyms

  • 1-Bromopyrrolidine-2,5-dione
  • 1-Bromo-2,5-pyrrolidinedione
  • NBS

Purity

>98%

Molecular Weight

176.943

Logp

0.4453

H Bond Acceptors

2

Fsp3

0.5

State

Solid

Melting Point

174 to 179°C

Boiling Range

338.9°C

Solubility

14.8g/L at 20°C

Vapour Pressure

0.001 Pa at 25°C

Partition Coefficient

-1.19

Auto Ignition Temp

>400°C

Explosive Properties

Not explosive.

Relative Density

2.098

Odour

pungent

SDS Documents

Pictograms

GHS03: Oxidizing
GHS05: Corrosive
GHS07: Harmful/Irritant
GHS09: Environmental Hazard

Signal Word

Danger

Hazard Statements

  • H272 – May intensify fire; oxidiser.
  • H290 – Maybe corrosive to metals.
  • H315 – Causes skin irritation.
  • H317 – May cause an allergic skin reaction.
  • H319 – Causes serious eye irritation.
  • H400 – Very toxic to aquatic life.

Precautionary Phrases

  • P210 – Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
  • P220 – Keep away from clothing and other combustible materials.
  • P234 – Keep only in original packaging.
  • P260 – Do not breathe dust/fume/gas/mist/vapours/spray.
  • P264 – Wash hands thoroughly after handling.
  • P270 – Do not eat, drink or smoke when using this product.
  • P271 – Use only outdoors or in a well-ventilated area.
  • P272 – Contaminated work clothing should not be allowed out of the workplace.
  • P273 – Avoid release to the environment.
  • P280 – Wear protective gloves/protective clothing and eye/face protection.
  • P301+P310 – IF SWALLOWED: Immediately call a POISON CENTER/doctor.
  • P301+P330+P331 – IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
  • P303+P361+P353 – IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water.
  • P304+P340 – IF INHALED: Remove person to fresh air and keep comfortable for breathing.
  • P305+P351+P338 – IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
  • P308+P313 – IF exposed or concerned: Get medical advice/attention.
  • P321 – Specific treatment (see Section 4 on this SDS).
  • P333+P313 – If skin irritation or rash occurs: Get medical advice/attention.
  • P361+P364 – Take off immediately all contaminated clothing and wash it before reuse.
  • P370+P378 – In case of fire: Use dry sand to extinguish.
  • P390 – Absorb spillage to prevent material damage.
  • P391 – Collect spillage.
  • P403+P233 – Store in a well-ventilated place. Keep container tightly closed.
  • P405 – Store locked up.
  • P406 – Store in a corrosion resistant container with a resistant inner liner.
  • P501 – Dispose of contents/container to hazardous waste disposal.

Un Number

3084

Packing Group

II

Hazard Class

8

Hazard Subclass

5.1

Shipping Name

CORROSIVE SOLID, OXIDIZING, N.O.S.

Download Certificate of Analysis

N-Bromosuccinimide Uses and Applications in Organic Synthesis

What is N-Bromosuccinimide (NBS)?

N-Bromosuccinimide (NBS) is a highly selective brominating reagent widely used in organic synthesis for allylic, benzylic, and electrophilic bromination reactions. It is valued in pharmaceutical R&D, fine chemical manufacturing, and CDMO process development due to its controlled reactivity, cleaner reaction profiles, and safer handling compared with elemental bromine.

NBS is commonly used for radical bromination, heterocycle functionalisation, halogenation of activated substrates, and oxidative transformations.

Primary Uses of N-Bromosuccinimide

1. Allylic Bromination (Wohl–Ziegler Reaction)

One of the most important N-Bromosuccinimide uses is allylic bromination, often referred to as the Wohl–Ziegler reaction.

Under radical conditions (AIBN, peroxide initiators, light, or heat), NBS selectively brominates the allylic position of alkenes while minimising addition across the double bond.

Applications include:

  • Pharmaceutical intermediate synthesis
  • Terpene and steroid modification
  • API building block preparation
  • Fine chemical development

NBS provides superior selectivity compared to molecular bromine by maintaining low in situ bromine concentration.

2. Benzylic Bromination

N-Bromosuccinimide is frequently used for benzylic bromination, converting alkylbenzenes into benzyl bromides.

This transformation is widely used in:

  • Medicinal chemistry programmes
  • Cross-coupling precursor synthesis
  • Alkylation reactions
  • Heterocycle functionalisation

NBS reduces unwanted aromatic ring bromination and improves reaction control under radical conditions.

3. Electrophilic Bromination of Alkenes

Under non-radical conditions, NBS acts as a controlled source of electrophilic bromine, enabling:

  • Vicinal dibromination
  • Bromohydrin formation
  • Halolactonisation reactions

These reactions are important in natural product synthesis, polymer chemistry, and advanced materials research.

4. Bromination of Heterocycles

NBS is commonly used for selective bromination of activated heterocycles such as:

  • Indoles
  • Pyrroles
  • Thiophenes
  • Electron-rich aromatic systems

Its controlled reactivity helps prevent polybromination, making it suitable for pharmaceutical and discovery chemistry applications.

5. Oxidative Transformations

In addition to bromination reactions, N-Bromosuccinimide participates in several oxidative processes, including:

  • Conversion of thiols to disulfides
  • Oxidative functional group activation
  • Selective transformations under mild conditions

These applications expand the versatility of NBS beyond halogenation chemistry.

Why Choose N-Bromosuccinimide?

Key advantages of NBS in synthesis:

  • High selectivity for allylic and benzylic positions
  • Controlled bromine release
  • Reduced side reactions
  • Cleaner reaction profiles
  • Easier handling compared with elemental bromine
  • Suitable for research and scalable industrial processes

Because of these advantages, N-Bromosuccinimide remains a cornerstone reagent in pharmaceutical development and fine chemical manufacturing.

Industries That Use NBS

  • Pharmaceutical R&D
  • CDMO process chemistry
  • Agrochemical synthesis
  • Polymer and materials research
  • Academic organic chemistry laboratories

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