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2-Iodoxybenzoic acid

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2-Iodoxybenzoic acid Basic information
Product Name:2-Iodoxybenzoic acid
Synonyms:2-Iodoxybenzoic Acid Stabilized (SIBX);2-Iodoxybenzoic Acid (stabilized with Benzoic Acid + Isophthalic Acid);1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide 97%, 45 wt. % IBX;SIBX, 1,3-Dihydro-1,3-dioxo-1-hydroxy-1,2-benziodoxole stabilised;Iodoxybenzoic aci;2-Iodoxybenzoic acid contains stabilizer, 45 wt. % (IBX);TRILON®;TRILON®BX
CAS:61717-82-6
MF:C7H5IO4
MW:280.02
EINECS:629-407-7
Product Categories:Fused Ring Systems;pharmacetical;API intermediates;Iodylbenzoic acid
Mol File:61717-82-6.mol
2-Iodoxybenzoic acid Structure
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
InChIInChI=1S/C7H5IO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)
InChIKeyCQMJEZQEVXQEJB-UHFFFAOYSA-N
SMILESC1(C(=O)O)C=CC=CC=1I(=O)=O
CAS DataBase Reference61717-82-6(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 
HS Code 29163990
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsEye Dam. 1
Skin Corr. 1
STOT RE 1 Inhalation
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
2-Iodoxybenzoic acid Usage And Synthesis
Chemical PropertiesWhite to off-white powder, prills or agglomerates
UsesStabilized 2-Iodoxybenzoic Acid (SIBX)
Uses2-Iodoxybenzoic Acid is used in the oxidation of alcohols in organic synthesis. It is also frequently used in the preparation of Dess-Martin periodinane.
DefinitionChEBI: 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 suitabilityreagent type: oxidant
Synthesis
2-Iodobenzoic acid

88-67-5

2-Iodoxybenzoic acid

61717-82-6

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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