69429-70-5

Basic information

• Product Name: 9-hydroxy-7,7-dimethyl-9$l^{3}-ioda-8-oxabicyclo[4.3.0]nona-1,3,5-trie ne
• Synonyms: 9-hydroxy-7,7-dimethyl-9$l^{3}-ioda-8-oxabicyclo[4.3.0]nona-1,3,5-trie ne;1,2-Benziodoxole, 1,3-dihydro-1-hydroxy-3,3-diMethyl-
• CAS NO: 69429-70-5
• Molecular Formula: C9H11IO2
• Molecular Weight: 278.08691
• Mol File: 69429-70-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 9-hydroxy-7,7-dimethyl-9$l^{3}-ioda-8-oxabicyclo[4.3.0]nona-1,3,5-trie ne(CAS DataBase Reference)
• NIST Chemistry Reference: 9-hydroxy-7,7-dimethyl-9$l^{3}-ioda-8-oxabicyclo[4.3.0]nona-1,3,5-trie ne(69429-70-5)
• EPA Substance Registry System: 9-hydroxy-7,7-dimethyl-9$l^{3}-ioda-8-oxabicyclo[4.3.0]nona-1,3,5-trie ne(69429-70-5)

Safety Data

• Hazardous Substances Data: 69429-70-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H11IO2/c1-9(2)7-5-3-4-6-8(7)10(11)12-9/h3-6,11H,1-2H3

Upstream product

• 69352-04-1 1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole 
• 69352-03-0 1-bromo-3,3-dimethyl-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole 
• 69352-05-2 2-(2-iodophenyl)propan-2-ol 
• 610-97-9 o-iodo-methyl-benzoic acid 

Downstream Products

• 1391728-13-4 1-fluoro-3,3-dimethyl-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole 

Relevant articles and documents

The direct electrophilic cyanation of β-keto esters and amides with cyano benziodoxole

The direct electrophilic α-cyanation of β-keto esters and amides has been developed using a hypervalent iodine benziodoxole-derived cyano reagent. The procedure is accomplished within 10 min and without the use of any catalyst in DMF, at room temperature. Thus, the highly functionalized quaternary carbon-centered nitriles were produced in high to excellent yields.

Ethynylbenziodoxolones (EBX) as reagents for the ethynylation of stabilized enolates

Herein, we report a detailed study on the electrophilic alkynylation of cyclic keto esters and amides with ethynylbenziodoxolone (EBX) reagents. The structure and stability of this class of reagents is first described more in details. Differential scannin

Electrophilic fluorination using a hypervalent iodine reagent derived from fluoride

The air and moisture stable fluoroiodane 8, readily prepared on a 6 g scale by nucleophilic fluorination of the hydroxyiodane 7 with TREAT-HF, has been used as an electrophilic fluorinating reagent for the first time to monofluorinate 1,3-ketoesters and d

Gold-catalyzed regioselective synthesis of 2- and 3-alkynyl furans

Chemical Matching: C2- or C3-alkynylated furans were selectively synthesized by using gold catalysis. Direct C-H alkynylation of furans was achieved with C2 selectivity, and a domino cyclization/alkynylation process starting from allenes gave C3-alkynylat

Ethynyl benziodoxolones for the direct alkynylation of heterocycles: Structural requirement, improved procedure for pyrroles, and insights into the mechanism

This report describes a full study of the gold-catalyzed direct alkynylation of indoles, pyrroles, and thiophenes using alkynyl hypervalent iodine reagents, especially the study of the structural requirements of alkynyl benziodoxolones for an efficient acetylene transfer to heterocycles. An improved procedure for the alkynylation of pyrroles using pyridine as additive is also reported. Nineteen alkynyl benziodoxol(on)es were synthesized and evaluated in the direct alkynylation of indoles and/or thiophenes. Bulky silyl groups as acetylene substituents were optimal. Nevertheless, transfer of aromatic acetylenes to thiophene was achieved for the first time. An accelerating effect of a methyl substituent in both the 3-and 6-position of triisopropylsilylethynyl-1,2-benziodoxol-3(1H)-one (TIPS-EBX) on the reaction rate was observed. Competitive experiments between substrates of different nucleophilicity, deuterium labeling experiments, as well as the regioselectivity observed are all in agreement with electrophilic aromatic substitution. Gold(III) 2-pyridinecarboxylate dichloride was also an efficient catalyst for the reaction. Investigations indicated that gold(III) could be eventually reduced to gold(I) during the process. As a result of these investigations, a π activation or an oxidative mechanism are most probable for the alkynylation reaction.

Organoiodinane Reagents for Phosphate Cleavage: Experimental and Computational Studies

Several analogues of 1-oxido-1,2-benziodoxol-3(1H)-one, 1 (the valence tautomer of o-iodosobenzoate), were examined for the ability to cleave p-nitrophenyl diphenyl phosphate in aqueous micellar cetyltrimethylammonium chloride at pH 8.These included the 5