Sodium ethanesulfinate Chemical Properties

Melting point:

292°C

Density 

1.372

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

Appearance

White to light yellow Solid

InChI

InChI=1S/C2H6O2S.Na/c1-2-5(3)4;/h2H2,1H3,(H,3,4);/q;+1/p-1

InChIKey

UWIVVFQECQYHOB-UHFFFAOYSA-M

SMILES

S(CC)(=O)[O-].[Na+]

Sodium ethanesulfinate Usage And Synthesis

Uses

The following Baran Sulfinate is a part of a toolbox of diversification reagents, which are ideal for the late-stage functionalization of nitrogen-containing heterocycles. The regioselectivity can be effectively tuned by modification of the pH and solvent selection.

Radical-Based Regioselective C–H Functionalization of Electron-Deficient Heteroarenes: Scope; Tunability; and Predictability

reaction suitability

reaction type: C-C Bond Formation
reagent type: catalyst
reaction type: C-H Activation

Synthesis

The general procedure for the synthesis of sodium ethylsulfite from ethylsulfonyl chloride was as follows: sodium sulfite (53.9 g, 0.428 mol), sodium bicarbonate (65.34 g, 0.778 mol), and deionized water (325 mL) were added to a four-necked flask equipped with a stirrer at room temperature and under nitrogen protection. The reaction mixture was stirred continuously at 80 °C for 1.3 hours. Subsequently, ethanesulfonyl chloride (50.0 g, 0.389 mol) was slowly added dropwise to the reaction system and the reaction continued to be stirred at the same temperature for 4.2 hours. Upon completion of the reaction, the reaction mixture was concentrated by rotary evaporator. Anhydrous ethanol was added to the concentrated residue and concentrated again. Next, toluene was added to the residue and the concentration process was repeated to completely remove water. The resulting solid was dried under vacuum, then anhydrous ethanol (100 mL) was added and the mixture was heated to reflux. The mixture was hot filtered and the solids were washed with a small amount of ethanol. All the filtrate and washings were combined and finally concentrated by rotary evaporator to give a white solid sodium ethylsulfite (38.96 g, yield calculated based on ethylsulfonyl chloride).

References

[1] RSC Advances, 2013, vol. 3, # 35, p. 15114 - 15120
[2] Chemistry - A European Journal, 2016, vol. 22, # 50, p. 18085 - 18091
[3] Macromolecules, 2018, vol. 51, # 20, p. 8188 - 8196
[4] Chemistry - A European Journal, 2016, vol. 22, # 25, p. 8694 - 8699
[5] Journal of Medicinal Chemistry, 1989, vol. 32, # 11, p. 2436 - 2442

Sodium ethanesulfinate(20035-08-9)Related Product Information

• Vinylferrocene
• Ethanesulfonamide
• ETHYLTRIMETHYLAMMONIUM IODIDE
• EUK 134
• VINYLCYCLOPENTANE
• Isopropenyl acetate
• Ethylenesulfonic acid
• thioacetic acid S-(3-broMopropyl) ester
• 1,1'-Bicyclohexyl,4-ethyl-4'-propyl-, (trans,trans)-
• Sodium 1-butanesulfonate
• Sodium 2-bromoethanesulphonate
• Sodium 1-hexanesulfonate
• 3-(TRIMETHYLSILYL)-1-PROPANESULFONIC ACID SODIUM SALT
• 1,2-NAPHTHOQUINONE-4-SULFONIC ACID SODIUM SALT
• Sodium 3-hydroxypropane-1-sulphonate
• Taurodeoxycholic acid sodium salt
• GLYOXAL SODIUM BISULFITE
• 1-DODECANESULFONIC ACID SODIUM SALT