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Sigma-Aldrich

Benzenesulfinic acid sodium salt

98%

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Synonym(s):
Sodium benzenesulfinate
Linear Formula:
C6H5SO2Na
CAS Number:
873-55-2
Molecular Weight:
164.16
Beilstein:
3598405
EC Number:
212-842-8
MDL number:
MFCD00013135
PubChem Substance ID:
24847576
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

mp

>300 °C (lit.)

SMILES string

[Na+].[O-]S(=O)c1ccccc1

InChI

1S/C6H6O2S.Na/c7-9(8)6-4-2-1-3-5-6;/h1-5H,(H,7,8);/q;+1/p-1

InChI key

CHLCPTJLUJHDBO-UHFFFAOYSA-M

Related Categories

General description

Benzenesulfinic acid sodium salt when treated with alkynylselenonium salts yields (Z)-β-alkoxyvinylsulfones. It undergoes rhodium-catalyzed desulfinative coupling with aldehydes to yield ketones.

Application

Benzenesulfinic acid sodium salt has been used in synthesis of sulfones by reaction of organic halides and sodium benzenesulfinate using higher alcohols or diols as solvents.It was also used in the synthesis of aryl sulfones via copper-catalyzed cross-coupling with boronic acids and vinyl sulfones via reaction with vicinal dibromides.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis, 1465-1465 (2007)
Reactions of alkynylselenonium salts with sodium benzenesulfinate.
Kataoka T, et al.
Tetrahedron Letters, 38(10), 1809-1812 (1997)
Rhodium-Catalyzed Aerobic Coupling between Aldehydes and Arenesulfinic Acid Salts: A Novel Synthesis of Aryl Ketones.
Rao H, et al.
Advanced Synthesis & Catalysis, 353(10), 1701-1706 (2011)
Sulfones from sodium benzenesulfinate.
Kauffman JM.
Journal of Chemical and Engineering Data, 14(4), 498-499 (1969)
Tetrahedron, 63, 7667-7667 (2007)
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