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Sigma-Aldrich

2-Iodobenzoic acid

≥99%, purified by sublimation

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About This Item

Linear Formula:
IC6H4CO2H
CAS Number:
88-67-5
Molecular Weight:
248.02
Beilstein/REAXYS Number:
1861406
EC Number:
201-850-7
MDL number:
MFCD00002419
UNSPSC Code:
12352100
PubChem Substance ID:
24866223

assay

≥99%

purified by

sublimation

mp

160-162 °C (lit.)

SMILES string

OC(=O)c1ccccc1I

InChI

1S/C7H5IO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)

InChI key

CJNZAXGUTKBIHP-UHFFFAOYSA-N

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General description

2-Iodobenzoic acid is a halogen substituted carboxylic acid.

Application

2-Iodobenzoic acid may be used for the following studies:
  • One-pot synthesis of hypervalent iodine reagent in the presence of trichloroisocyanuric acid (oxidant). This reagent is employed for the electrophilic trifluoromethylation reactions.
  • Synthesis of 1-arylbenziodoxolones.
  • Synthesis of isocoumarin.
  • Preparation of 2-iodoxybenzoic acid, using oxone (2KHSO5-KHSO4-K2SO4).

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Hypervalent iodine reagents for the oxidation of alcohols and their application to complex molecule synthesis.
Tohma H and Kita Y.
Advanced Synthesis & Catalysis, 346(2), 111-124 (2004)
Manab Chakravarty et al.
The Journal of organic chemistry, 71(24), 9128-9138 (2006-11-18)
Coupling reactions of allenylphosphonates (OCH(2)CMe(2)CH(2)O)P(O)CH=C=CRR' [R, R' = H (1a), R = H, R' = Me (1b), R = R' = Me (1c)] with aryl iodides, iodophenol, and iodobenzoic acid in the presence of palladium(II) acetate are investigated and compared
Václav Matoušek et al.
The Journal of organic chemistry, 78(13), 6763-6768 (2013-06-06)
Simplified syntheses suited for large scale preparations of the two hypervalent iodine reagents 1 and 2 for electrophilic trifluoromethylation are reported. In both cases, the stoichiometric oxidants sodium metaperiodate and tert-butyl hypochlorite have been replaced by trichloroisocyanuric acid. Reagent 1
Mekhman S Yusubov et al.
The Journal of organic chemistry, 78(8), 3767-3773 (2013-03-14)
Various 1-arylbenziodoxolones can be conveniently prepared from 2-iodobenzoic acid and arenes by a one-pot procedure using Oxone (2KHSO5·KHSO4·K2SO4) as an inexpensive and environmentally safe oxidant. This procedure is also applicable for the synthesis of the 7-methylbenziodoxolone ring system using 2-iodo-3-methylbenzoic
R E Rude et al.
The American journal of cardiology, 51(8), 1422-1427 (1983-05-01)
Ortho-iodo sodium benzoate (OISB) decreases the affinity of blood for oxygen, thus enhancing potential tissue oxygen delivery. To test the hypothesis that a change in oxygen affinity would ameliorate regional myocardial ischemic injury resulting from occlusion of the left anterior
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