35812-01-2

Basic information

• Product Name: N-BROMOSACCHARIN
• Synonyms: 2-BROMO-1,2-BENZISOTHIAZOL-3(2H)-ONE 1,1-DIOXIDE;N-BROMOSACCHARIN;N-Bromosaccharin,98%;2-bromo-1,1-dioxo-1,2-benzothiazol-3-one;N-Bromosaccharin;2-Bromobenzo[d]isothiazol-3(2H)
• CAS NO: 35812-01-2
• Molecular Formula: C₇H₄BrNO₃S
• Molecular Weight: 262.08
• EINECS: 252-737-4
• Product Categories: Bromination;Halogenation;Synthetic Organic Chemistry
• Mol File: 35812-01-2.mol

Chemical Properties

• Melting Point: 160 °C
• Boiling Point: 404.4°Cat760mmHg
• Flash Point: 198.3°C
• Appearance: /
• Density: 2.063g/cm³
• Vapor Pressure: 9.51E-07mmHg at 25°C
• Refractive Index: 1.714
• Storage Temp.: Refrigerator
• PKA: -24.37±0.20(Predicted)
• CAS DataBase Reference: N-BROMOSACCHARIN(CAS DataBase Reference)
• NIST Chemistry Reference: N-BROMOSACCHARIN(35812-01-2)
• EPA Substance Registry System: N-BROMOSACCHARIN(35812-01-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 35812-01-2(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white crystalline powder

InChI:InChI=1/C7H4BrNO3S/c8-9-7(10)5-3-1-2-4-6(5)13(9,11)12/h1-4H

Upstream product

• 81-07-2 saccharin 
• 128-44-9 saccharin sodium salt 

Downstream Products

• 133-42-6 D-galactonic acid 
• 3457-55-4 1-phenyl-1,2-butanedione 
• 81-07-2 saccharin 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 122-78-1 phenylacetaldehyde 
• 78-84-2 isobutyraldehyde 
• 50-00-0 formaldehyd 
• 75-07-0 acetaldehyde 

Relevant articles and documents

A convenient preparation of N-bromosaccharin, source of electrophilic bromine

An extremely straightforward, high yield synthesis of a very reactive electrophilic brominating reagent N-bromosaccharin is described, allowing its preparation in multi-gram quantities and in high purity.

Photochemical regioselective C(sp3)-H amination of amides using N-haloimides

A metal-free regioselective C(sp3)-H amination of amides using N-haloimides in the presence of lithium tert-butoxide and visible light is presented herein. This photoexcited approach is straightforward, and it aminates a wide variety of amides under mild conditions without the use of photocatalysts, external radical initiators, or oxidants. A halogen-bonded intermediate between the tert-butoxide base and the N-haloimide is proposed to be responsible for the increased photoreactivity. Calculations show that the formation of this electron donor-acceptor complex presents an exergonic energy profile.

Diastereoselective Electrophilic Trifluoromethylthiolation of Chiral Oxazolidinones: Access to Enantiopure α-SCF3 Alcohols

Lithium imide enolates featuring Evans’ chiral oxazolidinone auxiliary were involved in diastereoselective α-trifluoromethylthiolation with electrophilic SCF3 donors. Diastereopure products were isolated and converted to enantiopure α-SCF3 alcohols without racemisation. (Figure presented.).

PROCESS FOR THE PREPARATION OF ORGANIC BROMIDES

The present invention provides a process for the preparation of organic bromides, by a radical bromodecarboxylation of carboxylic acids with a bromoisocyanurate.

Lewis acid-catalyzed electrophilic trifluoromethylthiolation of (Hetero)arenes

(N-Trifluoromethylthio)saccharin has been applied as an electrophilic trifluoromethylthiolating reagent for a broad scope of heteroarenes, electron-donating group (EDG)-activated benzenes, and several electron-rich olefins. Iron(III) and gold(III) catalysts showed complementary activity for different substrates.

Visible-light promoted catalyst-free imidation of arenes and heteroarenes

We described herein a catalyst-free visible-light photolytic protocol for the imidation of arenes and heteroarenes. N-Bromosaccharin was identified as a viable and chemoselective nitrogen radical precursor that undergoes controllable homolytic cleavage under ambient light irradiation. The reaction can be applied to a number of arenes and heteroarenes with good chemo- and regioselectivity. Mechanistic studies revealed that radical chain termination by electron transfer-proton transfer (ET-PT) is the leading productive pathway for the reaction.

A peptide bromoiodinane approach for asymmetric bromolactonization

A series of 37 peptides containing an iodo-aryl amide active site were generated by means of both solid phase and conventional synthesis. These peptides were screened for asymmetric induction in the bromolactonization of 4-phenyl-4-pentenoic acid based on the generation of chiral bromoiodinane bromenium sources. The study culminated in the discovery of a tri-peptide iodo-aryl amide that effected the desired bromolactonization in quantitative conversion with 24% ee. The experiments disclosed herein provided valuable insight that ultimately facilitated the development of more synthetically useful enantioselective halocyclization methodology.

Conversion of nucleophilic halides to electrophilic halides: Efficient and selective halogenation of azinones, amides, and carbonyl compounds using metal halide/lead tetraacetate

AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc) 4 are efficient electrophilic N- and α-C-halogenating agents. A variety of azinones, amides and carbonyl compounds were chemoselectively and regioselectively N-, or α-C-halogenated in good to excellent yield using AlCl3/Pb(OAc)4 and ZnBr2/Pb(OAc)4 in acetonitrile. Georg Thieme Verlag Stuttgart.

A green preparation of N-chloro- and N-bromosaccharin

The reaction of the sodium salt of saccharin, potassium chloride or bromide and oxone in water at room temperature for 24h produced pure N-chloro- and N-bromosaccharin in 58% and 64% yield, respectively.