304-91-6

Basic information

• Product Name: 2-Iodosobenzoic acid
• Synonyms: 2-iodosyl-benzoicaci;2-iodosylbenzoicacid;o-iodoso-benzoicaci;o-iodosylbenzoicacid;1-HYDROXY-1,2-BENZIODOXOL-3(1H)-ONE;2-IODOSOBENZOIC ACID;O-IODOSOBENZOIC ACID;2-iodosobenzoic acid moistened with water (H2O ~10%)
• CAS NO: 304-91-6
• Molecular Formula: C₇H₅IO₃
• Molecular Weight: 264.02
• EINECS: 206-159-4
• Product Categories: Hypervalent Iodine Compounds;Oxidation;Synthetic Organic Chemistry;Reagents for Chemical Cleavage of Proteins;Enzymatic and Chemical Protein Cleavage;Mass Spectrometry;proteinmod
• Mol File: 304-91-6.mol

Chemical Properties

• Melting Point: 230 °C (dec.)(lit.)
• Appearance: White to off-white/Powder
• Storage Temp.: −20°C
• PKA: 2.84±0.36(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 1939973
• CAS DataBase Reference: 2-Iodosobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodosobenzoic acid(304-91-6)
• EPA Substance Registry System: 2-Iodosobenzoic acid(304-91-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DH3056550
• F: 8-23
• Hazardous Substances Data: 304-91-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Iodosobenzoic acid is used as a starting material for the preparation of 1-organosulfonyloxy-1,2-benziodoxol-3-(1H)-ones (3, 4, 5) through a one-step reaction with the corresponding sulfonic acids.
Used in Preparation of 2-carboxydiphenyliodonium Salts:
2-Iodosobenzoic acid is used as a reactant in the acid-catalyzed condensation with benzene, mesitylene, and cyclohexylbenzene to produce 2-carboxydiphenyliodonium salts, which are useful in various chemical reactions and applications.

Purification Methods

Crystallise the acid from EtOH and dry it in vacuo.[Beilstein 9 H 363.]

InChI:InChI=1/C7H5IO3/c9-7(10)5-3-1-2-4-6(5)8-11/h1-4H,(H,9,10)

Upstream product

• 88-67-5 2-Iodobenzoic acid 
• 26260-02-6 2-iodobenzaldehyde 
• 110349-22-9 2-dichloroiodanyl-benzoic acid ethyl ester 
• 79-21-0 peracetic acid 
• 64-19-7 acetic acid 
• 64297-64-9 2-iodoxybenzoic acid 
• 123-30-8 4-amino-phenol 
• 22695-76-7 (2-carboxy-phenyl)-dichloro-λ³-iodane 
• 7697-37-2 nitric acid 
• 67-66-3 chloroform 
• 7782-50-5 chlorine 
• 110-86-1 pyridine 
• 7664-93-9 sulfuric acid 
• 615-37-2 ortho-methylphenyl iodide 

Downstream Products

• 56-89-3 L-cystine 
• 64297-64-9 2-iodoxybenzoic acid 
• 69-72-7 salicylic acid 
• 155791-59-6 Phosphoric acid 3-oxo-3H-1λ³-benzo[d][1,2]iodoxol-1-yl ester diphenyl ester 
• 88-67-5 2-Iodobenzoic acid 
• 1829-26-1 1-acetoxy-1,2-benziodoxol-3-one 
• 101503-21-3 2-<4-Cyclohexyl-phenyljodonio>-benzoat 
• 5619-68-1 2',4',6'-Trimethyldiphenyliodonium-2-carboxylate 
• 1488-42-2 Diphenyliodonium-2-carboxylate 
• 160732-56-9 1-azido-1λ³-benzo[d][1,2]iodaoxol-3(1H)-one 
• 7782-50-5 chlorine 
• 1829-28-3 ethyl 2-iodobenzoate 
• 65-85-0 benzoic acid 
• 61717-82-6 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione 

Relevant articles and documents

METHOD FOR PRODUCING HYPERVALENT IODINE COMPOUND USING HYPOCHLORITE

PROBLEM TO BE SOLVED: To provide a method for producing a hypervalent iodine compound as a 2-iodobenzoic acid derivative that is safer and more convenient than the conventional method. SOLUTION: The method includes mixing 2-iodobenzoic acid as a starting material with hypochlorite or hypochlorite aqueous solution. During the reaction, depending on whether acetic acid or acetic anhydride is present or not in the mixture, IBA, IBA-OAc, IBX can be produced separately and selectively. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPO&INPIT

Metal-Free Electrophilic Alkynylation of Sulfenate Anions with Ethynylbenziodoxolone Reagents

Alkynyl sulfoxides are important building blocks with a unique reactivity in organic chemistry, but only a few reliable methods have been reported to synthesize them. A novel route to access alkynyl sulfoxides is reported herein by using ethynyl benziodoxolone (EBX) reagents to trap sulfenate anions generated in situ, via a retro-Michael reaction. The reaction takes place under metal-free and mild conditions. It is compatible with aryl, heteroaryl, and alkyl sulfoxides with up to 90% yield. This practical access to alkynyl sulfoxides is expected to facilitate the application of these useful building blocks in organic synthesis.

Preparation method of N-Boc biphenyl alaninal

The invention discloses a preparation method of N-Boc-biphenyl alaninal, and the preparation method comprises the following steps: the N-Boc-biphenyl alaninal can be obtained by oxidation reaction of N-Boc-biphenyl alaninol and 2-iodoxybenzoic acid in an organic solvent. The method has the advantages of simple operation, high yield, high purity, low cost and little pollution, and is suitable for industrial production.

Mild and efficient synthesis of iodylarenes using Oxone as oxidant

Mild and efficient method for the preparation of iodylarenes by oxidation of iodoarenes with Oxone in aqueous acetonitrile at room temperature is described. This new procedure allows the preparation of various iodylarenes with electron-donating or electron-withdrawing substituents in the aromatic ring including the previously unknown 1,2-diiodylbenzene.

Fast and highly chemoselective alkynylation of thiols with hypervalent iodine reagents enabled through a low energy barrier concerted mechanism

Among all functional groups, alkynes occupy a privileged position in synthetic and medicinal chemistry, chemical biology, and materials science. Thioalkynes, in particular, are highly useful, as they combine the enhanced reactivity of the triple bond with a sulfur atom frequently encountered in bioactive compounds and materials. Nevertheless, general methods to access these compounds are lacking. In this article, we describe the mechanism and full scope of the alkynylation of thiols using ethynyl benziodoxolone (EBX) hypervalent iodine reagents. Computations led to the discovery of a new, three-atom concerted transition state with a very low energy barrier, which rationalizes the high reaction rate. On the basis of this result, the scope of the reaction was extended to the synthesis of aryl- and alkyl-substituted alkynes containing a broad range of functional groups. New sulfur nucleophiles such as thioglycosides, thioacids, and sodium hydrogen sulfide were also alkynylated successfully to lead to the most general and practical method yet reported for the synthesis of thioalkynes.

FURO [3,2-B] PYRROL-3-ONE DERIVATIVES AND THEIR USE AS CYSTEINYL PROTEINASE INHIBITORS

The present invention relates to compounds of formula (I), and pharmaceutically acceptable salts thereof, A compound of formula (I), or a pharmaceutically acceptable salt, hydrate, complex or pro-drug thereof (I), wherein: one of R1 and R2 is H, and the other is selected from F and Cl, or R1 and R2 are both F; R3 is selected from cyclopentyl and cyclohexyl; R4 is an optionally substituted 5- or 6-membered monocyclic or an 8- to 10-membered bicyclic aryl or heteroaryl ring which includes up to four heteroatoms. The invention further relates to pharmaceutical compositions comprising compounds of formula (I), and the use of such compounds in the treatment of a disease selected from osteoporosis, Paget's disease, Chagas's disease, malaria, gingival diseases, hypercalaemia, metabolic bone disease, diseases involving matrix or cartilage degradation, and bone cancer disorders such as bone metastases and associated pain.

RuCl3-catalyzed oxidation of iodoarenes with peracetic acid: New facile preparation of iodylarenes

New facile methodology for the preparation of pentavalent iodine compounds using peracetic acid as an oxidant in the presence of catalytic amounts of ruthenium trichloride is described. The new procedure allows the preparation of several previously unknown iodylarenes bearing strongly electron-withdrawing CF3 groups in the aromatic ring.

Synthesis of novel, orthogonally protected multifunctional amino acids

Two synthetic strategies for the generation of differentially protected, chiral tri-amino acids have been developed. The first strategy is based on the reductive amination of a serine-derived oxazolidine aldehyde with mono N- protected ethylenediamine. The second approach involves reductive alkylation of an asparagine-derived N-protected diaminopropionate with an N-protected glycinal. The newly generated secondary amine functionality is derivatised to furnish structurally diverse molecules.

Enthalpies of combustion of 2-iodosobenzoic acid and 4-nitrosophenol: The dissociation enthalpy of the I-O bond

The standard (po = 0.1 MPa) molar enthalpies of combustion in oxygen, at T = 298.15 K, for crystalline 2-iodosobenzoic acid, (OI)C6H4COOH, and 4-nitrosophenol, (ON)C6H4OH, were measured by rotating-bomb calorimetry and static-bomb calorimetry, respectively. These values were used to derive the standard molar enthalpies of formation of the crystalline compounds. ΔfHom(cr)/(kJ · mol-1) 2-iodosobenzoic acid 2-(OI)C6H4COOH -336.9 ± 2.5 4-nitrosophenol 4-(ON)C6H4OH -70.2 ± 2.1 An indirect method was used for assessing the dissociation enthalpy of the (I-O) bond in the iodoso derivative, Dom(I-O)/(kJ · mol-1) = (264.5 ± 8.1), which is the first value reported for an iodine-oxygen bond in an organic molecule.

A Quantitative Description of the Effect of Cetyltrimethylammonium Bromide on the 2-Iodosylbenzoate-Catalysed Hydrolysis of Active Esters and Related Compounds

Apparent second-order rate constants (k2(app)) for the reaction of 2-iodosylbenzoate with 4-nitrophenyl diphenyl phosphate (3), 4-nitrophenyl acetate (4), 1-methylethyl methyl-phosphonofluoridate (5), 1,2,2-trimethylpropyl methylphosphonofluoridate (6) and ethyl N,N-dimethylphosphoramidocyanidate (7) in solutions of cetyltrimethylammonium bromide (ctab) were determined over a range of ctab concentrations.The profiles of k2(app) against were analysed to obtain second-order rate constants for the reaction in the micellar phase, and stability constants for the binding of reactants to the micellized detergent.Reaction rates in the micellar and bulk aqueous phases for each substrate are indistinguishable.The rate enhancements provided by the micellized ctab result from concentrating the reactants in the micellar phase.Substrates (5)-(7) are much less strongly bound to the micellized detergent than (3), and the maximum rate enhancements for these substrates are correspondingly smaller.