2-Iodosobenzoic acid

Base Information

• Chemical Name: 2-Iodosobenzoic acid
• CAS No.: 304-91-6
• Molecular Formula: C7H5IO3
• Molecular Weight: 264.019
• Hs Code.: 29163990
• European Community (EC) Number: 206-159-4
• NSC Number: 34548
• UNII: NVC3RT6T4K
• DSSTox Substance ID: DTXSID8075382
• Nikkaji Number: J96.188D
• Wikidata: Q27123560
• Metabolomics Workbench ID: 58349
• Mol file: 304-91-6.mol

Synonyms:2-iodosobenzoate;2-iodosobenzoic acid;ortho-iodosobenzoate;ortho-iodosobenzoic acid

Chemical Property of 2-Iodosobenzoic acid

Chemical Property:

• Melting Point: 230 °C (dec.)(lit.)
• PKA: 2.84±0.36(Predicted)
• PSA: 54.37000
• LogP: 1.87060
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 263.92834
• Heavy Atom Count: 11
• Complexity: 169

Purity/Quality:

99%, ^*data from raw suppliers

2-Iodosobenzoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)I=O
• Uses: 1-Organosulfonyloxy-1, 2-benziodoxol-3-(1H)-ones (3, 4, 5) can be prepared in one step from 2-iodosobenzoic acid and the corresponding sulfonic acids. 2-carboxydiphenyliodonium salts was prepared by the acid-catalyzed condensation of 2-iodosobenzoic acid with benzene, mesitylene, and cyclohexylbenzene.

Technology Process of 2-Iodosobenzoic acid

There total 19 articles about 2-Iodosobenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2-Iodobenzoic acid (88-67-5) → o-iodosobenzoic acid (304-91-6)

Guidance literature:

With sodium periodate; acetic acid; In water; for 4h; Reflux;

DOI:10.1021/acs.joc.9b00050

Reference yield: 96.6%

N-[(1R)-2-[1,1'-biphenyl]-4-yl-1-(hydroxymethyl)ethyl]carbamic acid tert-butyl ester (1426129-50-1) → o-iodosobenzoic acid (304-91-6) + (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanal (149709-58-0)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In 1,2-dimethoxyethane; at 75 - 85 ℃; for 1h; Temperature; Solvent; Industrial scale;

Reference yield: 85.0%

(3R,3aR,6S,6aS)-(9H-fluoren-9-yl)methyl 6-chloro-3-hydroxytetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate (1001548-05-5) → (3R,3aR,6S,6aS)-(9H-fluoren-9-yl)methyl 6-chloro-3-oxotetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate + o-iodosobenzoic acid (304-91-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 19h;

upstream raw materials:

2-Iodobenzoic acid

2-iodobenzaldehyde

2-dichloroiodanyl-benzoic acid ethyl ester

peracetic acid

Downstream raw materials:

L-cystine

2-iodoxybenzoic acid

salicylic acid

Phosphoric acid 3-oxo-3H-1λ³-benzo[d][1,2]iodoxol-1-yl ester diphenyl ester

Refernces

An efficient synthesis of iminoquinones by a chemoselective domino ortho-hydroxylation/oxidation/imidation sequence of 2-aminoaryl ketones

10.1039/c5ob02659h

The research aims to develop an efficient and environmentally friendly method for synthesizing iminoquinones, which are important in natural products and have diverse biological activities. The study introduces a chemoselective domino oxidative homocoupling of 2-aminoaryl ketones using 2-iodoxybenzoic acid (IBX) as the oxidant. The domino reaction involves three consecutive steps: ortho-hydroxylation of 2-aminoaryl ketones, oxidation of phenol derivatives to benzoquinones, and imine formation to yield iminoquinones. The researchers optimized the reaction conditions, finding that using 2 equivalents of IBX in DMSO at room temperature for 10 minutes provided the best results. The method allows for the recycling of IBX by converting the by-product iodosobenzoic acid (IBA) back to IBX. The study concludes that this domino strategy is highly chemoselective, efficient, and functional group tolerant, making it a viable approach for synthesizing iminoquinones from various substrates, including those containing sensitive functional groups.

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