• Chemical structure of PIDA ((diacetoxyiodo)benzene, phenyliodine(III) diacetate), CAS 3240-34-4, ≥97% — hypervalent λ³-iodane (C10H11IO4, 322.10) bearing two acetoxy groups on iodine. Used as a mild oxidant for alcohol and phenol oxidation, Hofmann-type rearrangements, α-functionalisation of ketones, and as the terminal oxidant in C–H amination and iodine(III) catalysis. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

PIDA ((Diacetoxyiodo)benzene)

CAS 3240-34-4 ≥97%

PIDA ((Diacetoxyiodo)benzene) | CAS 3240-34-4 | ≥97%

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Technical Specifications

CAS Number 3240-34-4
EC / EINECS Number 221-808-1
MDL Number MFCD00008692
RTECS Number DA3525000
SMILES CC(=O)OI(C1=CC=CC=C1)OC(=O)C
InChI InChI=1S/C10H11IO4/c1-8(12)14-11(15-9(2)13)10-6-4-3-5-7-10/h3-7H,1-2H3
InChIKey ZBIKORITPGTTGI-UHFFFAOYSA-N
PubChem CID 76724
Molecular Formula C₁₀H₁₁IO₄
Molecular Weight 322.1 g/mol
Melting Point 161-163 °C (lit.)
Solubility Soluble in acetic acid, acetonitrile and dichloromethane. Reacts with water.
Log Pow 2.8
Purity ≥97%
Physical Form White to light yellow crystal powder
HS Code 2915.39
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Light and moisture sensitive. Store in a dark place, sealed, in a dry place at room temperature.

Product Description & Scientific Applications

PIDA (iodobenzene diacetate; (diacetoxyiodo)benzene, phenyliodine(III) diacetate, PhI(OAc)2) is a hypervalent iodine(III) oxidant carrying two acetate ligands on a T-shaped iodine centre (C10H11IO4, 322.10 g/mol) — a metal-free alternative to heavy-metal oxidants across oxidation, cyclisation and C–H functionalisation.

It is used stoichiometrically, but the same chemistry can be run organocatalytically in the iodoarene by generating the iodine(III) species in situ from iodobenzene and mCPBA.

Applications and Reactions

  • Halocyclisation of olefins: effects haloamidation, haloetherification and halolactonisation of unfunctionalised olefins with regiocontrol.
  • Heterocycle synthesis: mediates intramolecular cyclisation of enamides to functionalised oxazoles, and acts as the sole iodine(III) reagent in intermolecular dehydrogenative annulation.
  • C–H functionalisation: under gold(III) catalysis it is the acetoxylation reagent for direct C–H acetoxylation of electron-rich arenes, and it enables distal C–H functionalisation of biarylsulfonanilides.
  • Oxidative aromatisation: aromatises Hantzsch 1,4-dihydropyridines to the corresponding pyridines.
  • Ring contraction: promotes ring contraction of cycloalkenes and cycloalkanones, and with iodine and iron dust activates one-pot oxidative decarboxylation–Friedel–Crafts sequences.
  • Terminal oxidant: with iron(III) porphyrins it oxidises bromomethyl groups to carboxylic acids, and it serves as the aryl source in palladium-catalysed ligand-free arylation of heteroaromatics.
  • Radical generation: oxidises N-hydroxy compounds to the corresponding aminoxyl (N-oxyl) radicals.
  • Alkynol acetoxylation: converts ethynylcarbinols to α,α′-diacetoxy ketones, and mediates metal-free three-component acetoxyaminoalkylation of α-diazo amides.
  • Handling: light and moisture sensitive; store sealed in a dark, dry place at room temperature.

Shipping Destinations

  • EU & UK: Priority delivery, 2–5 business days.
  • United States (DDP): 3–7 business days, duties and taxes prepaid.
  • EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
  • Worldwide: 7–14 business days, selected locations.

Safety Information

GHS Pictograms
GHS07 Harmful/Irritant
Signal Word Warning
Hazard Class Not regulated for transport
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)
H-Statements P264 - P280 - P302+P352 - P332+P313 - P337+P313 - P362+P364
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