| Identification | More | [Name]
N-Bromosuccinimide | [CAS]
128-08-5 | [Synonyms]
1-BROMO-2,5-PYRROLIDINEDIONE
2,5-PYRROLIDINEDIONE, 1-BROMO-
AKOS BBS-00004413
bromosuccinimide
BROMOSUCCINIMIDE-N
N-BROMOBUTANIMIDE
N-BROMOSUCCINIMIDE
N-BROMOSUCINIMIDE
NBS
SUCCINBROMIDE
SUCCINBROMIMIDE
SUCCINIMIDE, N-BROMO-
TIMTEC-BB SBB007826
1-Bromo-2,5-phrrolidinedione
1-bromo-5-pyrrolidinedione
5-Pyrrolidinedione,1-bromo-2
N-Bromsuccinimid
N-Brom-succinimid
N-Bromsuccinimide
Succinibromimide | [EINECS(EC#)]
204-877-2 | [Molecular Formula]
C4H4BrNO2 | [MDL Number]
MFCD00005510 | [Molecular Weight]
177.98 | [MOL File]
128-08-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystalline powder | [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. ]
0-6°C
| [solubility ]
14.8g/l (decomposition) | [form ]
Crystalline Powder | [pka]
-2.78±0.20(Predicted) | [color ]
White to light yellow | [Odor]
characteristic odour of bromine | [Stability:]
Stable. Incompatible with strong oxidizing agents, halogenated hydrocarbons. | [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 | [Detection Methods]
T(Iodometry) | [Merck ]
14,1438 | [BRN ]
113916 | [InChIKey]
PCLIMKBDDGJMGD-UHFFFAOYSA-N | [LogP]
-1.19 | [CAS DataBase Reference]
128-08-5(CAS DataBase Reference) | [NIST Chemistry Reference]
2,5-Pyrrolidinedione, 1-bromo-(128-08-5) | [Storage Precautions]
Moisture sensitive;Light sensitive | [EPA Substance Registry System]
128-08-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C,Xn | [Risk Statements ]
R22:Harmful if swallowed.
R34:Causes burns.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [Hazard Note ]
Harmful | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29251995 | [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. | [Hazardous Substances Data]
128-08-5(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: > 2000 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Succinic acid-->Succinimide | [Preparation Products]
alpha,alpha'-Dibromo-p-xylene-->4-Pyrazolecarboxylic acid-->METHYL ALPHA-BROMOPHENYLACETATE-->5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine-->2,1,3-BENZOTHIADIAZOL-4-YLMETHANOL,97%-->5-Bromo-4-chloro-2-(methylthio)-7H-pyrrolo[2,3-D]pyrimidine ,97%-->IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID-->METHYL 3-((PYRROLIDIN-1-YL)METHYL)BENZOATE-->5-BROMO-2-(PIPERIDIN-1-YL)PYRIMIDINE-->Methyl 3-(morpholinomethyl)benzoate ,98%-->5-BROMO-6-HYDROXY-1H-PYRIMIDINE-2,4-DIONE-->Ethyl 4-bromocrotonate-->5-BROMO-2-CHLORO-4,6-DIMETHYLNICOTINONITRILE-->5-BROMO-4,6-DIMETHOXYPYRIMIDINE-->4-BROMO-5-METHYL-1H-PYRAZOLE-3-CARBOXYLIC ACID-->2,5-DICHLOROTHIOPHENE-3-CARBOXYLIC ACID-->3-BROMO-5-(TRIFLUOROMETHYL)BENZENESULFONYL CHLORIDE-->4-Bromo-2-methoxyphenol-->5-Bromo-2-oxindole-->2-Hydroxy-5-bromopyridine-->3-Nitrobenzyl bromide-->8-BROMO-4-CHLORO-2-METHYLTHIOPYRAZOLO[1,5-A]1,3,5-TRIAZINE-->BISPYRAZOLONE-->METHYL 4-(BROMOMETHYL)-3-METHOXYBENZOATE-->2,6-Dibromopyridin-3-amine-->IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER-->2-Amino-5-bromopyrazine-->4-CHLORO-3-((CYCLOPROPYLAMINO)METHYL)BENZALDEHYDE-->4-AMINO-N,N-DIMETHYLBENZYLAMINE-->3-(BROMOMETHYL)BENZOIC ACID-->6-BROMOMETHYL-2-PYRIDINECARBOXYLIC ACID-->Methyl 2-bromomethylbenzoate-->DIETHYL 2-(ACETAMIDO)-2-(2-(BROMOMETHYL)-5-NITROBENZYL)MALONATE-->2-(Bromomethyl)pyridine hydrobromide-->5-BROMO-2-(MORPHOLIN-4-YL)PYRIMIDINE-->2-NAPHTHALEN-1-YL-ETHYLAMINE-->Bromoacetonitrile-->3-BROMO-1-(TRIISOPROPYLSILYL)INDOLE-->1-(BROMOMETHYL)-4-(METHYLSULFONYL)BENZENE |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystalline powder | [Uses]
In bromination of olefins; in oxidation of alcohols to aldehydes and ketones and of aldehydes to acid bromides. | [Uses]
N-Bromosuccinimide is a brominated succinimide used as a chemical reagent in radical substitution and electrophilic addition reactions in organic synthesis. | [Definition]
ChEBI: N-bromosuccinimide is a five-membered cyclic dicarboximide compound having a bromo substituent on the nitrogen atom. It has a role as a reagent. It is a dicarboximide, a pyrrolidinone and an organobromine compound. It is functionally related to a succinimide. | [Preparation]
N-Bromosuccinimide (128-08-5) 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.
| [Flammability and Explosibility]
Nonflammable | [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.] |
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