1-Hydroxy-3-oxo-1,3-dihydro-1,2-benzoiodoxole

Base Information

• Chemical Name: 1-Hydroxy-3-oxo-1,3-dihydro-1,2-benzoiodoxole
• CAS No.: 131-62-4
• Molecular Formula: C7H5IO3
• Molecular Weight: 264.019
• NSC Number: 364374
• DSSTox Substance ID: DTXSID00156834
• Nikkaji Number: J41.292I
• Wikidata: Q27123562
• Metabolomics Workbench ID: 58350
• ChEMBL ID: CHEMBL331810
• Mol file: 131-62-4.mol

Synonyms:131-62-4;1-Hydroxy-3-oxo-1,3-dihydro-1,2-benzoiodoxole;1-Hydroxy-1,2-benziodoxol-3(1H)-one;1-hydroxy-3-oxobenziodoxole;1,3-Dihydro-1-hydroxy-3-oxo-1,2-benziodoxole;NSC 364374;1-HYDROXY-2-OXA-1-IODA(III)INDAN-3-ONE;1-hydroxy-1lambda3,2-benziodoxol-3-one;MFCD01658875;1,2-Benziodoxole, 1,3-dihydro-1-hydroxy-3-oxo-;BRN 0140804;1,2-Benziodoxol-3(1H)-one, 1-hydroxy-;CHEBI:52699;1-hydroxy-1lambda(3),2-benziodoxol-3(1H)-one;1-Hydroxy-1lambda~3~,2-benziodoxol-3(1H)-one;4-27-00-09874 (Beilstein Handbook Reference);NSC364374;BR-43089;1-hydroxy-1l3-benzo[d][1,2]iodaoxol-3(1H)-one;CHEMBL331810;SCHEMBL1238997;DTXSID00156834;1-Hydroxy-1,2-benziodoxol-3-one;1-Hydroxy-1,2-benziodoxole-3-one;BBL102884;STL556692;AKOS015920407;NSC-364374;AS-19521;LS-33487;SY041374;1-hydroxy-1$l^{3},2-benziodoxol-3-one;CS-0086284;FT-0630110;1-hydroxy-3H-1lambda3,2-benziodaoxol-3-one;EN300-220562;A806291;AG-205/01862014;Q27123562

Chemical Property of 1-Hydroxy-3-oxo-1,3-dihydro-1,2-benzoiodoxole

Chemical Property:

• Melting Point: 260 °C (decomp)(Solv: water (7732-18-5))
• PKA: 8.12±0.20(Predicted)
• PSA: 46.53000
• LogP: 1.73550
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 263.92834
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Hydroxy-1,2-benziodoxol-3(1H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)OI2O
• Uses: 1-?Hydroxy-?1,?2-?benziodoxol-?3(1H)?-?one (IBA) is an efficient terminal oxidant for gold-?catalyzed, three-?component oxyarylation reactions. It also acted as a catalyst in synthesis of ynones via a hypervalent iodine-catalyzed reaction.

Technology Process of 1-Hydroxy-3-oxo-1,3-dihydro-1,2-benzoiodoxole

There total 29 articles about 1-Hydroxy-3-oxo-1,3-dihydro-1,2-benzoiodoxole 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) → 1-hydroxy-1,2-benzodioxol-3-(1H)-one (131-62-4)

Guidance literature:

With sodium (meta)periodate; acetic acid; In water monomer; for 4h; Reflux;

DOI:10.1002/chem.201001539

Reference yield: 96.0%

1-tosyloxy-1-oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one → 1-hydroxy-1,2-benzodioxol-3-(1H)-one (131-62-4)

Guidance literature:

With methanol; at 20 ℃; for 1h;

DOI:10.1039/c3cc47090c

Reference yield: 91.0%

2-Iodobenzoic acid (88-67-5) + water (7732-18-5) → 1-hydroxy-1,2-benzodioxol-3-(1H)-one (131-62-4)

Guidance literature:

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

water; at 20 ℃; for 1h;

DOI:10.1021/ja413208y

upstream raw materials:

ortho-methylphenyl iodide

2-Iodobenzoic acid

1-acetoxy-1,2-benziodoxol-3-one

2-Iodo-benzoic acid 2,3-bis-octanoyloxy-propyl ester

Downstream raw materials:

1-azido-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one

1-hexynyl-(o-carboxyphenyl)iodonium triflate

phenylethynyl(o-carboxyphenyl)iodonium triflate

3-oxo-1λ³-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile

Refernces

• 1、 Bertho, Sylvain,Rey-Rodriguez, Romain,Colas, Cyril,Retailleau, Pascal,Gillaizeau, Isabelle. "Regio- and Stereoselective Iron-Catalyzed Oxyazidation of Enamides Using a Hypervalent Iodine Reagent". . p. 17674 - 17677. Retrieved 2017.
• 2、 China, Hideyasu,Dohi, Toshifumi,Kageyama, Nami,Takenaga, Naoko,Yatabe, Hotaka. "Practical synthesis of 2-iodosobenzoic acid (IBA) without contamination by hazardous 2-iodoxybenzoic acid (IBX) under mild conditions". . . Retrieved 2021.
• 3、 Tessier, Romain,Nandi, Raj Kumar,Dwyer, Brendan G.,Abegg, Daniel,Sornay, Charlotte,Ceballos, Javier,Erb, Stéphane,Cianférani, Sarah,Wagner, Alain,Chaubet, Guilhem,Adibekian, Alexander,Waser, Jerome. "Ethynylation of Cysteine Residues: From Peptides to Proteins in Vitro and in Living Cells". . p. 10961 - 10970. Retrieved 2020.
• 4、 Yoshimura, Akira,Nguyen, Khiem C.,Rohde, Gregory T.,Saito, Akio,Yusubov, Mekhman S.,Zhdankin, Viktor V.. "Oxidative Cycloaddition of Aldoximes with Maleimides using Catalytic Hydroxy(aryl)iodonium Species". . p. 2340 - 2344. Retrieved 2016.
• 5、 Ballesteros, Anna,Granados, Albert,Vallribera, Adelina. "Enantioenriched Quaternary α-Pentafluoroethyl Derivatives of Alkyl 1-Indanone-2-Carboxylates". . p. 10378 - 10387. Retrieved 2020.
• 6、 Zhdankin, Viktor V.,Maydanovych, Olena,Herschbach, Jon,McDonald, Robert,Tykwinski, Rik R.. "Preparation, structure, and unexpected chemistry of phosphoranyl-derived benziodoxoles". . p. 11614 - 11615. Retrieved 2002.
• 7、 Borrel, Julien,Waser, Jerome. "Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations". supporting information. p. 142 - 146. Retrieved 2021/12/27.
• 8、 Le Du, Eliott,Robert, Emma G. L.,Waser, Jerome. "Synthesis of polycyclic aminal heterocycles via decarboxylative cyclisation of dipeptide derivatives". supporting information. p. 3473 - 3476. Retrieved 2022/03/31.