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N-Bromosuccinimide, 99%, Thermo Scientific Chemicals

Catalog No. AAA1592230
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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.

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

Specifications

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

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

RUO – Research Use Only

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