Thermo Scientific Chemicals

N-Bromosuccinimide, 99%, Thermo Scientific Chemicals

Catalog number: A15922.0B
1000 g, Each
Thermo Scientific Chemicals

N-Bromosuccinimide, 99%, Thermo Scientific Chemicals

Catalog number: A15922.0B
1000 g, Each
Quantity
Catalog number: A15922.0B
also known as A15922-0B
Price (EUR)
Quantity
-

Chemical Identifiers

CAS
128-08-5
IUPAC Name
1-bromopyrrolidine-2,5-dione
Molecular Formula
C4H4BrNO2
InChI Key
PCLIMKBDDGJMGD-UHFFFAOYSA-N
SMILES
BrN1C(=O)CCC1=O
Appearance (Color)
White to cream or pale yellow
Form
Powder or crystalline powder
Assay (Iodometric Titration)
≥98.5 to ≤101.5%
Identification (FTIR)
Conforms
Melting Point (clear melt)
173.0-182.0?C

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.
RUO – Research Use Only

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    Safety and Handling


    Classification of the substance or mixture
    CLP classification - Regulation(EC) No 1272/2008
    Oxidizing solids
    Category 3
    Substances/mixtures corrosive to metal
    Category 1
    Skin Corrosion/Irritation
    Category 2
    Serious Eye Damage/Eye Irritation
    Category 2
    Skin Sensitization
    Category 1
    Acute aquatic toxicity
    Category 1
    Label Elements
    Signal Word

    Warning

    Hazard Statements

    H272 - May intensify fire; oxidizer

    H315 - Causes skin irritation

    H317 - May cause an allergic skin reaction

    H319 - Causes serious eye irritation

    H400 - Very toxic to aquatic life

    Physical hazards

    H290 - May be corrosive to metals

    Precautionary Statements

    P210 - Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking

    P280 - Wear protective gloves/protective clothing/eye protection/face protection

    P302 + P352 - IF ON SKIN: Wash with plenty of soap and water

    P333 + P313 - If skin irritation or rash occurs: Get medical advice/attention

    P337 + P313 - If eye irritation persists: Get medical advice/attention

    P371 + P380 + P375 - In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion