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
• Article Data: 13

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

Chemical Properties

White powder

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.

Definition

ChEBI: A benzoic acid compound having an iodosyl substituent at the ortho-position.

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 
• 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 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 1001548-05-5 (3R,3aR,6S,6aS)-(9H-fluoren-9-yl)methyl 6-chloro-3-hydroxytetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate 
• 1426129-50-1 N-[(1R)-2-[1,1'-biphenyl]-4-yl-1-(hydroxymethyl)ethyl]carbamic acid tert-butyl ester 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 22695-76-7 (2-carboxy-phenyl)-dichloro-λ³-iodane 
• 64297-64-9 2-iodoxybenzoic acid 

Downstream Products

• 69-72-7 salicylic acid 
• 88-67-5 2-Iodobenzoic acid 
• 5619-68-1 2',4',6'-Trimethyldiphenyliodonium-2-carboxylate 
• 1488-42-2 Diphenyliodonium-2-carboxylate 
• 61717-82-6 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione 
• 66146-33-6 2-(3-nitrophenyl)acetaldehyde 
• 201470-89-5 5-formylfuro<2,3-b>pyridine 
• 184969-65-1 3-(3,4-dichlorophenyl)-5-(4-hydroxy-4-phenyl-1-piperidinyl)-2-(2-methoxyimino)pentanal 
• 1377861-15-8 1-[2,4,6-trimethylphenylethynyl]-1,2-benziodoxol-3(1H)-one 
• 1610967-53-7 1-{[2-azido-5-(trifluoromethyl)phenyl]ethynyl}-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one 
• 1610967-55-9 1-[(2-azido-4-chlorophenyl)ethynyl]-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one 
• 1610967-52-6 methyl 3-azido-4-[(3-oxo-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl)ethynyl]benzoate 
• 1610967-54-8 1-[(2-azido-4-methylphenyl)ethynyl]-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one 
• 8039-03-0 Co(CN)(CH₃)8(CH₂CONH₂)3((CH₂)2CONH₂)3N₄C₁₂(CH)7N₂C₇(CH₃)2H₂C₄OHOCH₂OHH₄OPO₃CHCH₃CH₂NHCO(CH₂)2 

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

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.

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.