Hypodiphosphorous tetraiodide

Base Information

• Chemical Name: Hypodiphosphorous tetraiodide
• CAS No.: 13455-00-0
• Molecular Formula: I4P2
• Molecular Weight: 569.566
• European Community (EC) Number: 236-646-7
• DSSTox Substance ID: DTXSID6065474
• Nikkaji Number: J166.100K
• Wikipedia: Diphosphorus tetraiodide
• Wikidata: Q412973
• Mol file: 13455-00-0.mol

Synonyms:Diphosphorus tetraiodide;13455-00-0;Hypodiphosphorous tetraiodide;diiodophosphanyl(diiodo)phosphane;Diphosphorous tetraiodide;Phosphorus iodide;Diphosphorus tetraiodide, 95%;EINECS 236-646-7;tetraiododiphosphane;periododiphosphine;Tetraiododiphosphine;Diphosphine, tetraiodo-;I4P2;P2I4;DTXSID6065474;I4-P2;MFCD00011526;AKOS015916035;Q412973;J-006558

Chemical Property of Hypodiphosphorous tetraiodide

Chemical Property:

• Appearance/Colour: orange to red powder
• Melting Point: 124-127 °C(lit.)
• PSA: 27.18000
• LogP: 5.26520
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 569.5654
• Heavy Atom Count: 6
• Complexity: 26.5

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tetraiododiphosphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: P(P(I)I)(I)I
• General Description: Diphosphorus tetraiodide (P2I4), also known as phosphorus iodide, diphosphorus tetraiodide, phosphorous diiodide, or tetraiododiphosphine, is a mild condensing agent used in organic synthesis, particularly for converting oximes of α-diketones into oxadiazoles and nitriles. It facilitates dehydration and rearrangement reactions, enabling the formation of 1,2,5-oxadiazoles and 1,2,4-oxadiazoles, as well as nitriles, under mild conditions. The reagent is effective in chlorinated solvents like dichloromethane, making it a useful tool for synthesizing heterocyclic compounds with potential bioactivity.

Technology Process of Hypodiphosphorous tetraiodide

There total 44 articles about Hypodiphosphorous tetraiodide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

phosphorous + iodine (7553-56-2,12190-71-5,8031-47-8) → diphosphorus tetraiodide (13455-00-0)

Guidance literature:

In neat (no solvent); heating mixture of 1 Mol I2 and 0.75 Mol red P and stirring for 1 h at 180°C after reaction took place;; dissolving in boiling chlorobenzene, filtering off, washing crystals with hot CHCl3 and drying in vacuum;;

Reference yield:

iodine (7553-56-2,12190-71-5,8031-47-8) + phosphorus trichloride (7719-12-2,52843-90-0) → diphosphorus tetraiodide (13455-00-0)

Guidance literature:

In acetic acid; react. with iodine in glacial acetic acid; formation of P2I4 or PI3 depending on ratio of educts;;

DOI:10.1021/ja01401a001

Reference yield:

iodine (7553-56-2,12190-71-5,8031-47-8) + phosphan (7803-51-2) → diphosphorus tetraiodide (13455-00-0) + hydrogen iodide (10034-85-2)

Guidance literature:

In neat (no solvent); heating I2 with dry PH3 in excess; formation of P2I4 and HI;;

upstream raw materials:

iodine

phosphorus trichloride

phosphan

phosphonium iodide

Downstream raw materials:

5-(3,5-Dichloro-phenylsulfanyl)-1-isopropyl-4-pyridin-4-ylmethyl-1H-pyrazole-3-carboxylic acid ethyl ester

phosphan

phosphorus trichloride

iodine

Refernces

Reaction of oximes of-diketones with diphosphorous tetraiodide for preparation of oxadiazoles and nitriles

10.1080/00397911.2011.595035

The study primarily investigates the use of diphosphorus tetraiodide (P2I4) as a novel and mild condensing agent for the synthesis of oxadiazoles and nitriles from the oximes of α-diketones. The research explores the dehydration of oximes to form 1,2,5-oxadiazoles and the rearrangement of oximes to produce the normal Beckmann product, 1,2,4-oxadiazole. Key chemicals used in the study include dioximes derived from α-diketones, such as benzildioxime, and various substituted 1,2-dioximes, which serve as substrates for the synthesis of oxadiazoles. The study also examines the effects of different solvents on the reaction, with chlorinated solvents, particularly dichloromethane, proving to be the most effective. The purpose of these chemicals is to facilitate the synthesis of oxadiazoles, which are an important class of heterocycles used in a variety of bioactive molecules, and nitriles, through a simple and efficient method.

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