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8.14815

Sigma-Aldrich

Sodium chlorite

(25% solution in water) for synthesis

Synonym(s):

Chlorous acid, sodium salt

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About This Item

UNSPSC Code:
12352302
NACRES:
NA.22

vapor pressure

20 hPa ( 20 °C)

Quality Level

200

form

liquid

potency

1136 mg/kg LD50, oral (Rat)

pH

12-13 (20 °C in H2O)

bp

≥100 °C/1013 hPa

mp

<-3 °C

density

1.20-1.25 g/cm3 at 20 °C

storage temp.

2-30°C

Application

Sodium chlorite (NaClO2) can be used as an oxidizing agent for the conversion of:
  • Aldehydes to corresponding carboxylic acids under mild reaction conditions in the presence of scavengers such as sulfamic acid or resorcinol.
  • Primary alcohols to carboxylic acids in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and NaOCl.
  • Aliphatic and aromatic thiols to the corresponding disulfides.
  • Aryl boronic acids to phenols via ipso-hydroxylation.
  • Cyclic benzylic ethers and N-protected cyclic benzylic amines to benzolactones and benzolactams.
  • Alkenes to epoxides using aldehydes as promoters.
  • Alkenes and cycloalkenes to 1, 2 diols via osmium-catalyzed Sharpless asymmetric dihydroxylation.

It can also be used in combination with Br2 to synthesize 2-carboxyazetidin-2-ones from furanylazetidinones.

Analysis Note

Assay (iodometric): 23.0 - 26.0 %
Density (d 20 °C/ 4 °C): 1.200 - 1.220

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1 - STOT RE 2

Target Organs

spleen

Supplementary Hazards

EUH032

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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ipso-Hydroxylation of Arylboronic Acids and Boronate Esters by Using Sodium Chlorite as an Oxidant in Water
Gogoi P, et al.
European Journal of Organic Chemistry, 2013(32), 7291-7294 (2013)
Uses of sodium chlorite and sodium bromate in organic synthesis. A review
Krapcho A Paul
Organic preparations and procedures international, 38(2), 177-216 (2006)
Epoxidation by sodium chlorite with aldehyde-promoted chlorine dioxide formation
Jangam A and Richardson DE
Tetrahedron Letters, 51(50), 6481-6484 (2010)
A simple and effective synthesis of benzolactones and benzolactams by noncatalytic benzylic oxidation of cyclic benzylic ethers and N-protected cyclic benzylic amines with sodium chlorite as an oxidant
Song Ai-Ru, et al.
Synthesis, 44(18), 2903-2909 (2012)

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