N-Bromosuccinimide, 99%, Thermo Scientific Chemicals

Description

N-Bromosuccinimide is a chemical reagent used in electrophilic additions and radical substitution reactions in synthetic organic chemistry. In Wohl-Ziegler reaction, it is involved in allylic and benzylic bromination reaction. It is also used in the alfa-bromination of carbonyl derivatives. In the Hofmann rearrangement, it is used in the presence of a strong base, such as 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) reacts with primary amides to produce a carbamate. It oxidizes silyl ethers to aldehydes in the presence of azobisisobutyronitrile. It is also used for the modification of ribosomal sulfhydryl groups.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
N-Bromosuccinimide is a chemical reagent used in electrophilic additions and radical substitution reactions in synthetic organic chemistry. In Wohl-Ziegler reaction, it is involved in allylic and benzylic bromination reaction. It is also used in the alfa-bromination of carbonyl derivatives. In the Hofmann rearrangement, it is used in the presence of a strong base, such as 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) reacts with primary amides to produce a carbamate. It oxidizes silyl ethers to aldehydes in the presence of azobisisobutyronitrile. It is also used for the modification of ribosomal sulfhydryl groups.

Solubility
Soluble in acetone, tetrahydrofuran, dimethyl formamide, dimethyl sulfoxide and acetonitrile. Slightly soluble in water and acetic acid. Insoluble in ether, hexane and carbon tetrachloride.

Notes
Moisture and light sensitive. Incompatible with strong oxidizing agents, strong acids, strong bases, iron, iron salts, halogenated hydrocarbons, amines and metals. Store in a cool place.

Specifications

Chemical Identifiers

• CAS: 128-08-5
• Molecular Formula: C4H4BrNO2
• Molecular Weight (g/mol): 177.985
• MDL Number: MFCD00005510
• InChI Key: PCLIMKBDDGJMGD-UHFFFAOYSA-N
• Synonym: n-bromosuccinimide, succinbromimide, succinbromide, succinibromimide, n-bromosuccimide, 2,5-pyrrolidinedione, 1-bromo, 1-bromo-2,5-pyrrolidinedione, bromosuccinimide, nbs, n-bromo succinimide
• PubChem CID: 67184
• ChEBI: CHEBI:53174
• IUPAC Name: 1-bromopyrrolidine-2,5-dione
• SMILES: C1CC(=O)N(C1=O)Br

• Melting Point: 175°C to 180°C (decomposition)
• Density: 2.098
• Assay Percent Range: 99%
• Quantity: 250 g
• UN Number: UN3261
• Beilstein: 113916
• Sensitivity: Light sensitive
• Merck Index: 14,1438
• Solubility Information: Soluble in acetone,tetrahydrofuran,dimethyl formamide,dimethyl sulfoxide and acetonitrile. Slightly soluble in water and acetic acid. Insoluble in ether,hexane and carbon tetrachloride.
• Formula Weight: 177.99
• Percent Purity: 99%
• Chemical Name or Material: N-Bromosuccinimide

Safety and Handling

Hazard Category	H272-H290-H315-H317-H319
Hazard Statement	GHS H Statement H314-H318-H302 Causes severe skin burns and eye damage. Causes serious eye damage. Harmful if swallowed.
Precautionary Statement	P210-P220-P221-P234-P261-P264b-P272-P280-P302+P352-P305+P351+P338-P333+P313-P362-P370+P378q-P390-P501c
DOTInformation	Hazard Class: 8; Packaging Group: II
EINECSNumber	204-877-2
TSCA	Yes
storageNote1	Moisture sensitive
Recommended Storage	Ambient temperatures

SDS

RUO – Research Use Only