23178-73-6

Upstream product

• 618-51-9 3-Iodobenzoic acid 
• 65-85-0 benzoic acid 

Downstream Products

• 64297-65-0 3-iodylbenzoic acid 
• 64297-60-5 m-iodosylbenzoic acid 

Relevant academic research and scientific papers

Ceric ammonium nitrate as the novel oxidizing agent for the facile synthesis of (dichloroiodo)arenes

Ceric ammonium nitrate (CAN) has been found to be a remarkable oxidizing agent for the oxidative conversion of iodoarenes to (dichloroiodo)arenes in acetic acid using aqueous HCl. The reaction of CAN with HCl generates in situ molecular chlorine, which is responsible for the oxidation. This method avoids the use of hazardous, toxic, and corrosive gaseous chlorine.

Conversion of aryl iodides into aryliodine(III) dichlorides by an oxidative halogenation strategy using 30% aqueous hydrogen peroxide in fluorinated alcohol

Oxidative chlorination with HCl/H2O2 in 1,1,1-trifluoroethanol was used to transform aryl iodides into aryliodine(III) dihalides. In this instance 1,1,1-trifluoroethanol is not only the reaction medium, but is also an activator of hy

Synthesis and reactivity of fluorous and nonfluorous aryl and alkyl iodine(III) dichlorides: New chlorinating reagents that are easily recycled using biphasic protocols

Fluorous aryl and alkyl iodine(III) dichlorides of the formulas (R fn(CH2)3)2C6H 3ICl2 (Rfn ) CF3(CF 2)n-1; n ) 8 for 3,5-disubstituted and n ) 6, 8, 10 for 2,4-disubstituted) and RfnCH2ICl2 (n ) 8, 10) are prepared in 71-98% yields by reactions of Cl2 and the corresponding fluorous iodides. These are effective reagents for the conversions of cyclooctene to trans-1,2-dichlorocyclooctene, anisole to 4-chloro- and 2-chloroanisole, 4-tert-butylphenol to 2-chloro-4-tert-butylphenol, PhCOCH 2COPh to PhCOCHClCOPh, and PhCOCH3 to PhCOCH2Cl and PhCOCHCl2 (CH3CN, rt to 40°C, 100-64% conversions). The chlorinated products and fluorous iodide coproducts are easily separated by organic/fluorous liquid/liquid biphase workups. The latter are obtained in 97-90% yields and reoxidized with Cl2. Analogous chlorinations are conducted with 3-Cl2IC6H4COOH (16) and 4,4'-Cl2IC6H4C6H 4ICl2. With the former, the products and coproduct 3-IC6H4COOH (91-85% recoveries) are easily separated by organic/aqueous NaHCO3 liquid/ liquid biphase workups. The coproduct from the latter, 4,4'-IC6H4C6H4I, is insoluble in common organic solvents, allowing separation by liquid/solid phase workups (91-89% recoveries). The effect of the structure of the iodine(III) dichloride upon reactivity is analyzed in detail. The fluorous systems with Rf8 substituents are generally superior, but 16 is more reactive and gives higher selectivities.

4,4′-Bis(dichloroiodo)biphenyl and 3-(dichloroiodo)benzoic acid: New recyclable hypervalent iodine reagents for vicinal halomethoxylation of unsaturated compounds

4,4′-Bis(dichloroiodo)biphenyl and 3-(dichloroiodo)benzoic acid are convenient recyclable hypervalent iodine reagents for vicinal chloromethoxylation or iodomethoxylation of unsaturated compounds. The reactivity of these reagents in the reaction of vicinal halomethoxylation is generally similar to dichloroiodobenzene and the advantage of their use is that the reduced forms of these reagents can be easily separated from the reaction mixture and reused for the regeneration of the reagents.

A solvent-free synthesis of (dichloroiodo)arenes from iodoarenes

An efficient solid-state oxidation of iodoarenes, ArI, is described using the urea-hydrogen peroxide adduct (UHP), a stable, inexpensive, and easily handled oxidant. The reactions were complete in 15min at 85°C. The melts thus obtained were reacted with e

One-pot preparations of (dichloroiodo)arenes from some arenes

Arenes (ArH) were substituted with some transient I3+ species, generated in situ in appropriate, anhydrous I2/NaIO4 or NaIO3/AcOH/Ac2O/concd H2SO4 mixtures, to form soluble organ

One-pot procedures for preparing (dichloroiodo)arenes from arenes and diiodine, with chromium(VI) oxide as the oxidant

Ten representative (dichloroiodo)arenes, ArICl2, were prepared from the corresponding arenes and diiodine in variable anhydrous mixtures, ArH/I2/CrO3/AcOH/Ac2O/conc. H 2SO4, followed by the

Novel oxidative, liquid-phase chlorination procedures for the preparation of (dichloroiodo)arenes from iodoarenes

One improved and eight novel oxidative, liquid-phase chlorination procedures for the preparation of (dichloroiodo)arenes, ArICl2, from iodoarenes, ArI, are presented. KMnO4, activated MnO2, KCIO3, NaIO4/su

Liquid-phase and biphasic chlorination of some iodoarenes to form (dichloroiodo)arenes with sodium peroxodisulfate as the oxidant

Liquid-phase and biphasic (CCl4/concd hydrochloric acid) chlorination of some iodoarenes to form the corresponding (dichloroiodo)arenes, prepared in 60-100% crude yields, are reported; dichlorine is produced as follows: Na2S2OP8 + 2 HCl (conc. aq.) → Cl2 + 2 NaHSO4.

Oxidative chlorination of various lodoarenes to (dichloroiodo)arenes with chromium(vi) oxide as the oxidant j

Chromium(vi) oxide dissolved in a mixture of acetic acid with concentrated hydrochloric acid converts, at or near room temperature, iodoarenes to (dichloroiodo)arenes, in a very simple and efficient procedure.