Sodium bromite

• CAS: 7486-26-2
• Catalog Number: ACM7486262
• Category: Main Products
• Molecular Weight: 134.89
• Molecular Formula: BrNaO₂
• Synonyms: Sodium bromite (NaBrO2); Sodium bromite (6CI,7CI); Bromousacid,sodium salt (8CI,9CI); EINECS 231-290-9; sodium hypobromate; Sodium bromite; Bromous acid,sodium salt; Bromous acid,sodium salt (1:1)
• IUPAC Name: sodium;bromite
• Canonical SMILES: [O-]Br=O.[Na+]
• InChI Key: NYCVSSWORUBFET-UHFFFAOYSA-M
• Appearance: White Crystal
• EC Number: 231-290-9
• Exact Mass: 133.89800

Case Study

Study on the oxidation method of alcohols using sodium bromite

Inokuchi, Tsutomu, et al. The Journal of Organic Chemistry 55.2 (1990): 462-466.

Oxidation of primary and secondary alcohols to aldehydes, carboxylic acids and ketones has been carried out in an N-oxyammonium salt-NaBrO2 system. Sodium bromite was used as a stoichiometric oxidant to activate N-oxy compounds (recovered catalyst) to their N-oxyammonium salts in a weakly alkaline medium, preferentially oxidizing primary hydroxyl groups rather than secondary hydroxyl groups to the corresponding aldehydes. Calcium hypochlorite was used as an alternative terminal oxidant in the same medium. This method is applicable to the selective formation of γ- and 6-lactones, β-hydroxyaldehydes and 2-acetoxyketones, and has advantages in terms of reagent cost, safety and operational simplicity.
Undecanol (3a, 1.72 g, 10 mmol) was dissolved in 5% NaHCO3 aqueous solution (100 mL). After cooling to 0-5°C, sodium bromite (6.2 g, 30 mmol) was added to the above mixture under moderate stirring. Stirring was continued for another 3 hours at room temperature, and ethanol (5 drops) was added. The organic layer was separated, the aqueous layer was extracted with CH2Cl2, the combined extracts were washed with brine, dried (Na2SO4), and the residue was flash chromatographed on silica gel (hexanes-AcOEt).

Studies on the formation of carbonyl compounds assisted by sodium bromite

Morimoto, Takashi, et al. Journal of the Chemical Society, Perkin Transactions 1 8 (1988): 2423-2424.

Oxidation of various alcohols with sodium bromite was performed in dichloromethane in the presence of alumina. When benzyl alcohol was used as a substrate, the reaction flask was flushed with argon due to the sensitivity of the product to auto-oxidation. The oxidation of benzyl alcohol proceeded smoothly to produce aldehydes or ketones in good yields. The ring substituents had little effect on the yields: even p-nitro derivatives gave the corresponding benzaldehydes in fairly good yields. Aliphatic secondary alcohols also oxidized smoothly to ketones in excellent yields. Some differences in reaction time were due to differences in substrate reactivity, but except in the case of cyclohexanol, 24 h reactions gave satisfactory yields of carbonyl compounds.
Sodium bromite trihydrate (0.63 g, 3.3 mmol) was added to alumina in dichloromethane (10 ml), followed by 4-tert-butylcyclohexanol (0.50 g, 3.2 mmol), and a small amount of solvent. The mixture was stirred at ambient temperature for 24 h. The solution was filtered through sintered glass and the solid was washed thoroughly with the same solvent or ether (about 100 ml). The combined filtrates were evaporated under reduced pressure to give 4-tert-butylcyclohexanone (0.48 g, 98%).

Synthesis of N-bromoimides using sodium bromite

Kajigaeshi, Shoji, et al. Bulletin of the Chemical Society of Japan 58.2 (1985): 769-770.

N-bromoimides can be easily prepared in high yields under mild conditions by reacting imides with sodium bromite in the presence of hydrobromic acid. Recently, a new reagent, sodium bromite (NaBrO2), has emerged in organic synthesis. While studying the synthetic utility of sodium bromite, researchers found that N-bromoimides can be produced in high yields by reacting imides with sodium bromite in the presence of hydrobromic acid under mild conditions.
A 94.7% aqueous solution of sodium bromite was added to an aqueous solution of 1a. 47% hydrobromic acid was slowly added dropwise to the cold solution with stirring, and the reaction mixture was stirred for another 10 minutes. The precipitate obtained was filtered, washed with cold water and dried at room temperature to give 2a as white crystals. A 94.7% solution of sodium bromite in water was added to a solution of 1b and sodium hydroxide in water. To the ice-cold solution, 47% hydrobromic acid was slowly added dropwise with stirring, and then the reaction mixture was further stirred for 10 minutes at 0° C. The obtained precipitate was filtered, washed with cold water and dried at room temperature to obtain white crystals 2b.

Simultaneous bromination and creaming of unsaturated diols with sodium bromite

Evans, Gary B., and Peter K. Grant.Tetrahedron letters 38.26 (1997): 4709-4712.

Attempts to lactonize unsaturated diols with sodium bromite in aqueous acetic acid gave bromodiols, respectively. Bromodiols were reacted with Jones reagent to give the corresponding lactones. The synthesis of lactones has structural similarities to flavor ingredients and intermediates, and a key step in their synthesis is the lactonization of their appropriate precursors. The use of sodium bromite in aqueous acetic acid has been reported. A series of diols were levorotated in moderate to excellent yields (54-95%). Bromate has been previously reported as an oxidizing agent and has been shown to undergo addition reactions with olefins, which can be explained by the addition of bromine. Attempts to levorotate saturated 1,5-diols. Treatment with sodium bromite in aqueous acetic acid gave a mixture of isoxime ketones.
Lactation of unsaturated 1,5-diols with sodium bromite in aqueous acetic acid. The unsaturated diol was synthesized in six steps from manol. The key reaction was the treatment of the epoxyacetate with methanesulfonyl chloride in refluxing pyridine. A mixture of two allylic alcohols was thus obtained, from which the desired unsaturated alcohol was isolated in moderate yield (27%) after careful chromatography. The compound was quantitatively reduced to the unsaturated diol using LiAlH4.

Custom Q&A

What is the molecular formula of Sodium bromite?

The molecular formula of Sodium bromite is NaBrO2.

What are the synonyms for Sodium bromite?

The synonyms for Sodium bromite are bromous acid, sodium salt and bromous acid, sodium salt (1:1).

What is the molecular weight of Sodium bromite?

The molecular weight of Sodium bromite is 134.89 g/mol.

When was Sodium bromite created?

Sodium bromite was created on February 5, 2008.

When was Sodium bromite last modified?

Sodium bromite was last modified on October 21, 2023.

What is the IUPAC name of Sodium bromite?

The IUPAC name of Sodium bromite is sodium;bromite.

What is the InChI of Sodium bromite?

The InChI of Sodium bromite is InChI=1S/BrHO2.Na/c2-1-3;/h(H,2,3);/q;+1/p-1.

What is the InChIKey of Sodium bromite?

The InChIKey of Sodium bromite is NYCVSSWORUBFET-UHFFFAOYSA-M.

What is the CAS number of Sodium bromite?

The CAS number of Sodium bromite is 7486-26-2.

What is the formal charge of Sodium bromite?

The formal charge of Sodium bromite is -1.