Synthesis of (diacetoxyiodo)benzene (iodobenzene diacetate; iodosobenzene diacetate)

Preparation of (diacetoxyiodo)benzene

Preparation of (diacetoxyiodo)benzene (iodobenzene diacetate; iodosobenzene diacetate)

Preparation of (diacetoxyiodo)benzene (iodobenzene diacetate; iodosobenzene diacetate)

2 g of iodosobenzene are added to 6 ml of glacial acetic acid. The mixture is boiled gently until a clear solution is obtained, and then cooled to the room temperature. The iodosobenzene diacetate is freely soluble in acetic acid, but not in ethyl ether. Therefore 50 ml of ethyl ether is added in order to precipitate the iodobenzene diacetate. The precipitated colorless crystals are filtered, wash with ether, and dried yielding 2 g of final product, which melts at 157° C. (Diacetoxyiodo)benzene could be purified by recrystallization from benzene. Unlike the dichloride, it is stable on being kept. Iodosobenzene with dilute nitric acid gives the dinitrate, C6H5I(NO3)2

Practical organic chemistry, by F. G. Mann, 86-88, 1960

IUPAC Name

[acetyloxy(phenyl)-$l^{3}-iodanyl] acetate

InChI

InChI=1S/C10H11IO4/c1-8(12)14-11(15-9(2)13)10-6-4-3-5-7-10/h3-7H,1-2H3

InChI Key

ZBIKORITPGTTGI-UHFFFAOYSA-N

Canonical SMILES

CC(=O)OI(C1=CC=CC=C1)OC(=O)C

MeSH Synonyms

((diacetoxy)iodo)benzene, DAIB cpd, phenyliodosodiacetate

Depositor-Supplied Synonyms

(Diacetoxyiodo)benzene, Iodobenzene diacetate, 3240-34-4, Iodosobenzene diacetate, Phenyliodine diacetate, Phenyliodo diacetate, Phenyliodoso acetate, Phenyliodoso diacetate, Bis(acetato)phenyliodine, Benzene, (diacetoxyiodo)-, Phenyliodosodiacetate, Phenyliodine(III) diacetate, Phenyliodosyl diacetate, Benzene, iodoso-, diacetate, Iodine, bis(acetato-O)phenyl-, Iodobenzene I,I-diacetate, NSC 23801, Benzene, (dihydroxyiodo)-, diacetate, Bis(acetato-O)phenyliodine, Iodosobenzene I,I-diacetate, ZBIKORITPGTTGI-UHFFFAOYSA-N, Iodine, bis(acetato-kappaO)phenyl-, EINECS 221-808-1, BIS(ACETYLOXY)(PHENYL)-LAMBDA3-IODANE, acetyloxyiodophenylmethyl acetate, bis(acetyloxy)(phenyl)-lambda~3~-iodane, Benzene, diacetate, [acetyloxy(phenyl)-, DAIB, PubChem2143, (acetyloxy)(phenyl)-, diacetoxy(phenyl)-iodane, [bis(acetoxy)iodo]benzene, AC1L2RJ1, AC1Q1L8Q, SCHEMBL47350, KSC676Q1R, iodine, bis(acetyloxy)phenyl-, phenyl-l3-iodanediyl diacetate, 178721_ALDRICH, Jsp005988, 31490_FLUKA, CTK5H6818, MolPort-001-770-059, BB_SC-7036, ACT04334, NSC23801, ANW-27345, BBL009751, CD-712, NSC-23801, NSC226375, SBB058234, STL145789, IODINE, BIS(ACETATO-KO)PHENYL, AKOS005146479, Iodine, bis(acetato-.kappa.O)phenyl-, AB00949, AC-1473, Iodine, bis(acetato-O)phenyl- (9CI), MCULE-8639370732, NSC-226375, RTC-060463, (acetyloxy)(phenyl)-|E?-iodanyl acetate, (acetyloxy)(phenyl)-|E3-iodanyl acetate, AK-43305, AN-14902, BC220419, BR-43305, H409, LS-30388, SC-03462, WLN: 1VO-I-R &OV1 &5/10, [acetoxy(phenyl)-$l^{3}-iodanyl] acetate, AB1001958, TC-060463, AM20120551, FT-0082625, I0330, ST24032066, ST51016023, A25390, S-7837, Diacetoxyiodosobenzene; Iodobenzene i,i-diacetate, [ACETOXY(PHENYL)-LAMDBA(3)-IODANYL] ACETATE, (ACETYLOXY)(PHENYL)-LAMBDA(3)-IODANYL ACETATE, 3B3-008475, Iodobenzene I; I-diacetate; Iodosobenzene I; I-diacetate, 207518-80-7, 359635-52-2, 76546-99-1, 864365-82-2, 864365-83-3

Removed Synonyms

benzene, Iodosobenzenediacetate, DIACETOXYIODOSOBENZENE, CID76724, 94569-95-6, DIB, PIA

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