2-Iodoxybenzoic acid Chemical Properties

Melting point:

280 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Very Slightly, Heated)

form 

powder to crystal

color 

White to Almost white

Merck 

14,5048

InChI

InChI=1S/C7H5IO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)

InChIKey

CQMJEZQEVXQEJB-UHFFFAOYSA-N

SMILES

C1(C(=O)O)C=CC=CC=1I(=O)=O

CAS DataBase Reference

61717-82-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi,Xn

Risk Statements 

22-34-44-42/43-36/37/38-20/21/22-37-35-1

Safety Statements 

26-36/37/39-45-22-35

RIDADR 

UN 1759 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

Ⅱ

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich

2-Iodoxybenzoic acid Usage And Synthesis

Chemical Properties

White to off-white powder, prills or agglomerates

Uses

Stabilized 2-Iodoxybenzoic Acid (SIBX)

Uses

2-Iodoxybenzoic Acid is used in the oxidation of alcohols in organic synthesis. It is also frequently used in the preparation of Dess-Martin periodinane.

Definition

ChEBI: A benziodoxole compound having hydroxy and oxo substituents at the 1-position and an oxo substituent at the 3-position.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 4155, 1983 DOI: 10.1021/jo00170a070

reaction suitability

reagent type: oxidant

Synthesis

General procedure for the synthesis of 2-iodobenzoic acid from 2-iodobenzoic acid: note: IBX may explode when subjected to shock or heated to over 200 °C. IBX was prepared with reference to the method described by Sputore and coworkers.In a 500 mL round bottom flask equipped with a mechanical stirrer, 2-iodobenzoic acid (12.5 g, 50.4 mmol) was added to a solution of Oxone (40.281 g, 65.5 mmol) in deionized water (163 mL). The reaction mixture was heated to 73 °C and stirred vigorously at this temperature for 3 hours. Subsequently, the reaction mixture was cooled to 0 °C and continued to stir slowly for 1.5 hours. The mixture was filtered through a porous glass funnel and the resulting white solid was washed sequentially with deionized water (730 mL) and acetone (235 mL). Finally, the product was dried under high vacuum for 2 days to afford 2-iodoylbenzoic acid as a white solid in 84% yield (11.848 g, 42.3 mmol).

References

[1] European Journal of Organic Chemistry, 2012, # 7, p. 1439 - 1447
[2] Journal of Organic Chemistry, 1983, vol. 48, # 22, p. 4155 - 4156
[3] Journal of the American Chemical Society, 1991, vol. 113, # 19, p. 7277 - 7287
[4] Journal of Organic Chemistry, 2005, vol. 70, # 17, p. 6991 - 6994
[5] Tetrahedron, 2002, vol. 58, # 23, p. 4573 - 4587

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