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A15922 N-Bromosuccinimide, 99%

CAS Number
128-08-5
Synonyms
NBS

Stock No. Size Price ($) Quantity Availability
A15922-30 250g 38.90
A15922-0B 1000g 114.00
A15922-0I 5000g 461.00
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N-Bromosuccinimide, 99%

MDL
MFCD00005510
EINECS
204-877-2

Chemical Properties

Formula
C4H4BrNO2
Formula Weight
177.99
Melting point
175-180° dec.
Density
2.098
Storage & Sensitivity
Light Sensitive. Ambient temperatures.
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.

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.

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.

Literature References

Source of free-radical or positive bromine. For examples of radical benzylic bromination (Wohl-Ziegler), see: Org. Synth. Coll., 4, 921 (1963); 5, 145, 329, 825 (1973). The use of the ozone depleting solvent CCl4 has been avoided by the use of the ionic liquid 1-n-Butyl-3-methyl­imidazolium hexafluorophosphate, L19086 : Synlett, 702 (2003). Cleavage of carbohydrate benzyl ethers: J. Org. Chem., 55, 378 (1990), and of benzyl esters: Synlett, 219 (1994), occur under mild conditions; the benzyl group is converted to benzaldehyde. For allylic bromination, see e.g.: Org. Synth. Coll., 4, 108 (1963);.9, 112, 191 (1998) review: Chem. Rev., 43, 271 (1948).

For free-radical ɑ-bromination of a Boc glycine ester, see: Org. Synth. Coll., 9, 526 (1998).

Both aliphatic and aromatic aldehydes are converted to acyl bromides under free-radical conditions: Tetrahedron Lett., 3809 (1979); Synlett, 347 (1990); Tetrahedron Lett., 31, 7237 (1990).

In acetonitrile, NBS is a mild and regiospecific nuclear brominating agent for activated aromatics such as methoxybenzenes and naphthalenes: J. Org. Chem., 60, 5328 (1995). Deactivated aromatics, e.g. nitroarenes and benzotrifluorides, can be m-brominated under mild conditions in good yield with NBS in TFA, in the presence of H2SO4: Synlett, 1245 (1999).

In the presence of a phosphine or phosphite, converts alcohols to alkyl bromides with inversion: Tetrahedron Lett., 3937 (1973). For a review of this and related reactions, see: Org. React., 29, 1 (1983).

Alkenes undergo trans-addition reactions with NBS in combination with a nucleophile. For examples, see: Org. Synth. Coll., 6, 184, 560 (1988). With alcohols, bromohydrin ethers are formed. For use in the synthesis of cyclopropenone, see: Org. Synth. Coll., 6, 361 (1988):

In the presence of DBU in MeOH, amides rearrange to amines in good yields, providing a mild and efficient alternative to the classical Hofmann halogen/ caustic alkali conditions: J. Org. Chem., 62, 7495 (1997).

Examples of the use of NBS as a mild, selective oxidizing agent:

Sulfides to sulfoxides: J. Org. Chem., 37, 3976 (1968). Oximes to nitrile oxides: J. Org. Chem., 37, 436 (1968). Secondary alcohol in the presence of primary: Tetrahedron Lett., 2745 (1979). (In DMSO): Alkynes to ɑ-diketones: Can. J. Chem., 49, 1099 (1979).

(Free radical): Aldehydes to acyl bromides or amides: Tetrahedron Lett., 31, 7237 (1990). Benzyl silyl ethers to aldehydes: Synlett, 345 (1990). Aldehydes to esters: Synlett, 347 (1990).

For use as a mild catalyst in acetalization reactions, see Triethyl­ orthoformate, A13587 .

For a brief feature on uses in synthesis, see: Synlett, 498 (2006). See also 1,3-Dibromo-5,5-dimethyl­hydantoin, A15510 .

Guha, S.; Rajeshkumar, V.; Kotha, S. S.; Sekar, G. A Versatile and One-Pot Strategy to Synthesize alpha-Amino Ketones from Benzylic Secondary Alcohols Using N-Bromosuccinimide. Org. Lett. 2015, 17 (3), 406-409.

Wang, W. X.; Zhang, Q. Z.; Zhang, T. Q.; Li, Z. S.; Zhang, W.; Yu, W. N-Bromosuccinimide-Mediated Radical Cyclization of 3-Arylallyl Azides: Synthesis of 3-Substituted Quinolines. Adv. Synth. Catal. 2015, 357 (1), 221-226.

GHS Hazard and Precautionary Statements

Hazard Statements: H272-H290-H315-H317-H319

May intensify fire; oxidizer. May be corrosive to metals. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye irritation.

Precautionary Statements: P210-P220-P221-P234-P261-P264b-P272-P280-P302+P352-P305+P351+P338-P333+P313-P337+P313-P362-P370+P378q-P390-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep/Store away from clothing/combustible materials. Take any precaution to avoid mixing with combustibles. Keep only in original container. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If skin irritation or rash occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Absorb spillage to prevent material damage. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,1438
Beilstein
113916
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2925.19
TSCA
Yes

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