N-Bromosuccinimide

Base Information

• Chemical Name: N-Bromosuccinimide
• CAS No.: 128-08-5
• Deprecated CAS: 133435-75-3,3493-39-8,3493-39-8
• Molecular Formula: C4H4BrNO2
• Molecular Weight: 177.985
• Hs Code.: 29251995
• European Community (EC) Number: 204-877-2
• NSC Number: 16
• UNII: K8G1F2UCJF
• DSSTox Substance ID: DTXSID2038738
• Nikkaji Number: J5.405D
• Wikipedia: N-Bromosuccinimide
• Wikidata: Q286939
• Metabolomics Workbench ID: 58582
• Mol file: 128-08-5.mol

Synonyms:Bromosuccinimide;N Bromosuccinimide;N-Bromosuccinimide;Succinbromimide

Chemical Property of N-Bromosuccinimide

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 0.107mmHg at 25°C
• Melting Point: 173- 176°C
• Refractive Index: 1.606
• Boiling Point: 221.4 °C at 760 mmHg
• PKA: -2.78±0.20(Predicted)
• Flash Point: 87.7 °C
• PSA: 37.38000
• Density: 2.042 g/cm³
• LogP: 0.38320
• Storage Temp.: 0-6°C
• Sensitive.: Moisture Sensitive
• Solubility.: 14.8g/l (decomposition)
• Water Solubility.: Soluble in acetone, tetrahydrofuran, dimethyl formamide, dimethyl sulfoxide and acetonitrile. Slightly soluble in water and acet
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 176.94254
• Heavy Atom Count: 8
• Complexity: 129

Purity/Quality:

99%min ^*data from raw suppliers

N-Bromosuccinimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xn
• Hazard Codes: C,Xn
• Statements: 22-34-36/37/38
• Safety Statements: 26-36/37/39-45-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Succinimides
• Canonical SMILES: C1CC(=O)N(C1=O)Br
• Chemical Structure: N-Bromosuccinimide (NBS) consists of a succinimide ring with a bromine atom attached. ^[1]
• Uses: NBS is a highly useful reagent in organic synthesis. It is categorized as an organic brominating agent. Widely employed in various organic transformations, including radical or electrophilic substitutions, electrophilic additions, oxidations, and Hofmann rearrangement. Particularly utilized for the bromination of aliphatic and aromatic hydrocarbons, with applications in electrophilic aromatic substitution reactions. ^[1]; NBS is commonly used as an oxidizing agent in organic synthesis, including antibiotics like levofloxacin (LF). It falls under the category of N-halo compounds and is known for its capacity to oxidize various substrates. ^[2]; In the chemical and pharmaceutical industries, NBS is a commonly used bromination reagent for regulating low-energy bromination reactions.
• History and Development: The first reported iodine-catalyzed bromination of aromatic compounds by NBS dates back to one century ago. Subsequent studies have explored the role of iodine in catalyzing bromination reactions, with advancements in understanding the mechanism and reaction design. ^[1]
• Analysis Method: The purity of NBS can be checked iodometrically. Various analytical techniques such as UV-Vis spectrophotometry, FT-IR spectroscopy, LC-MS, and NMR spectroscopy are employed to characterize reaction products and intermediates. ^[2]
• Production Methods: The preparation method of NBS usually involves synthesizing ammonium succinate from succinic acid and ammonia, then heating and dehydrating it to form succinimide, and then brominating and refining it to obtain the finished product. The purity can generally reach 90% to 97%.
• References: [1] Mechanistic study on iodine-catalyzed aromatic bromination of aryl ethers by N-Bromosuccinimide (DOI 10.1016/j.tet.2017.10.073); [2] Studies on the oxidation of levofloxacin by N-bromosuccinimide in acidic medium and their mechanistic pathway (DOI 10.1016/j.molliq.2016.02.051)

Technology Process of N-Bromosuccinimide

There total 18 articles about N-Bromosuccinimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

Succinimide (123-56-8,89963-74-6) → N-Bromosuccinimide (128-08-5)

Guidance literature:

With hydrogenchloride; sodium chlorite; sodium bromide; In water; at 0 - 25 ℃; for 1.5h; Temperature;

Reference yield: 76.0%

→ N-Bromosuccinimide (128-08-5)

Guidance literature:

Reference yield:

2-(4-methylphenyl)-2-(N-bromo-p-toluene-sulfonamide)-1-bromo-ethane + Succinimide (123-56-8,89963-74-6) → N-Bromosuccinimide (128-08-5) + 2-bromo-1-(4-methylphenyl)-1-(p-toluenesulfonamido)ethane

Guidance literature:

In dichloromethane-d2;

upstream raw materials:

Succinimide

N-bromoacetamide

N-chloro-succinimide

benzotelluracyclopentane bromide succinimide

Downstream raw materials:

2-oxo-propionic acid ethyl ester

3-methyl-2-ketobutanoic acid

isobutyraldehyde

2,5-di-tert-butyl-[1,4]benzoquinone-bis-bromoimine

Refernces

• 1、 Lamchen. "-". . p. 747. Retrieved 1950.
• 2、 Lind, Johan,Shen, Xinhua,Eriksen, Trygve E.,Merényi, Gábor,Eberson, Lennart. "One-Electron Reduction of N-Bromosuccinimide. Rapid Expulsion of a Bromine Atom". . p. 4629 - 4633. Retrieved 1991.
• 3、 Mohite, Amar R.,Phatake, Ravindra S.,Dubey, Pooja,Agbaria, Mohamed,Shames, Alexander I.,Lemcoff, N. Gabriel,Reany, Ofer. "Thiourea-Mediated Halogenation of Alcohols". . p. 12901 - 12911. Retrieved 2020/11/26.
• 4、 ?ebular, Klara,Bo?i?, Bojan ?.,Stavber, Stojan. "Esterification of aryl/alkyl acids catalysed by n-bromosuccinimide under mild reaction conditions". . . Retrieved 2018/09/10.