ChemicalBook Product Catalog Chemical Reagents Organic reagents Amide N-Bromosuccinimide

N-Bromosuccinimide

CAS128-08-5

MFC4H4BrNO2

MW177.98

EINECS204-877-2

Chemical Properties

Melting point	175-180 °C (dec.)(lit.)
Boiling point	221.4°C (rough estimate)
Density	2.098
vapor pressure	14.8 hPa (20 °C)
refractive index	1.6060 (estimate)
storage temp.	Store at +2°C to +8°C.
solubility	14.8g/l (decomposition)
pka	-2.78±0.20(Predicted)
form	Crystalline Powder
color	White to light yellow
Odor	characteristic odour of bromine
Water 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.
Sensitive	Moisture Sensitive
Merck	14,1438
BRN	113916
Stability	Stable. Incompatible with strong oxidizing agents, halogenated hydrocarbons.
InChIKey	PCLIMKBDDGJMGD-UHFFFAOYSA-N
CAS DataBase Reference	128-08-5(CAS DataBase Reference)
NIST Chemistry Reference	2,5-Pyrrolidinedione, 1-bromo-(128-08-5)
EPA Substance Registry System	N-Bromosuccinimide (128-08-5)

Safety Information

Hazard Codes	C,Xn
Risk Statements	22-34-36/37/38
Safety Statements	26-36/37/39-45-37/39
RIDADR	UN 3261 8/PG 2
WGK Germany	3
Hazard Note	Harmful
TSCA	Yes
HazardClass	8
PackingGroup	III
HS Code	29251995
Hazardous Substances Data	128-08-5(Hazardous Substances Data)
Toxicity	LD50 orally in Rabbit: > 2000 mg/kg

MSDS

Usage And Synthesis

Chemical Properties

white to light yellow crystalline powder
Uses

N-Bromosuccinimide is a brominated succinimide used as a chemical reagent in radical substitution and electrophilic addition reactions in organic synthesis.
Uses

In bromination of olefins; in oxidation of alcohols to aldehydes and ketones and of aldehydes to acid bromides.
Uses

NBS, is a chemical reagent used in organic chemistry in electrophilic addition reactions and radical substitution
Preparation

N-Bromosuccinimide (NBS) is a widely used mild brominating agent and used as chemical intermediate and building block for several chemical production processes, especially in pharma related applications.

1.62mol (160g) succinimide is dissolved in a mixture of 1.60mol (64g) NaOH, 300g crushed ice and 400ml water. Cool the mixture in an ice bath, and add 85ml (1.65 mol, 264g) Br2 at once while stirring violently. Stir for two more minutes, then filter the precipitated product and wash with ice water. Dry in a desiccator. Yield 75-81%.
Don't clean up NBS too much, the stinky yellow stuff still containing a bit of Br2 works best.
Definition

ChEBI: A five-membered cyclic dicarboximide compound having a bromo substituent on the nitrogen atom.
Safety Profile

Poison by intraperitoneal route. An irritating poison to skin, eyes, and mucous membranes. Reacts explosively with adme, dtallyl sulfide, and hydrazine hydrate. Explosive reaction with propiononitrile after heating to 105℃ for 24 hours. Violent reaction with dtbenzoyl peroxide + 4-tok acid. When heated to decomposition it emits toxic fumes of Brand NOx. See also BROMIDES and NITROGEN MONOXIDE.
Purification Methods

N-Bromosuccinimide (30g) is purified by dissolving rapidly in 300mL of boiling water and filtering through a fluted filter paper into a flask immersed in an ice bath, and left for 2hours. The crystals are filtered off, washed thoroughly with ca 100mL of ice-cold water and drained on a Büchner funnel before drying under vacuun over P2O5 or CaCl2 [Dauben & McCoy J Am Chem Soc 81 4863 1959]. This brominating agent has also been crystallised from acetic acid or water (10 parts), washed in water and dried in vacuo [Wilcox et al. J Am Chem Soc 108 7693 1986, Shell et al. J Am Chem Soc 108 121 1986, Phillips & Cohen J Am Chem Soc 108 2013 1986, Beilstein 21/9 V 543.]

N-Bromosuccinimide

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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