Diiodotriphenylphosphorane

Base Information

• Chemical Name: Diiodotriphenylphosphorane
• CAS No.: 6396-07-2
• Molecular Formula: C18H15 I2 P
• Molecular Weight: 516.1
• European Community (EC) Number: 627-787-9
• DSSTox Substance ID: DTXSID70213802
• Nikkaji Number: J50.355J
• Wikidata: Q83089404
• Mol file: 6396-07-2.mol

Synonyms:Diiodotriphenylphosphorane;6396-07-2;Phosphorane, diiodotriphenyl-;Iodotriphenylphosphoranium iodide;diiodo(triphenyl)-lambda5-phosphane;BRN 2740417;I2-PPh3;diiodo(triphenyl)-5-phosphane;SCHEMBL525224;DIIDOTRIPHENYLPHOSPHORANE;DTXSID70213802;AC9088;MFCD00216568;AKOS015916033;SY263442;LS-107452;CS-0203211;4-16-00-01013 (Beilstein Handbook Reference);Triphenylphosphine diiodide, technical grade, 90%

Chemical Property of Diiodotriphenylphosphorane

Chemical Property:

• Melting Point: 210-220 °C(lit.)
• PSA: 13.59000
• LogP: 5.21620
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 515.90008
• Heavy Atom Count: 21
• Complexity: 285

Purity/Quality:

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

TRIPHENYLPHOSPHINE DIIODIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34-42/43-62
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)(C3=CC=CC=C3)(I)I
• Uses: Triphenylphosphine diiodide (Ph3P. I2) can be used as a reagent: To facilitate the conversion of alcohol, thiol, and enol functional groups into alkyl iodides via formation of alkoxyphosphonium iodide. To prepare β-iodo-α,β-unsaturated ketones from cyclic β-diketones in the presence of triethyl amine. In the synthesis of alkyl nitrates from alcohols. In the Beckmann rearrangement reaction to synthesize lactams from cycloalkanone oxime. For the preparation of aromatic and aliphatic carboxylic acid esters in the presence of N,N-dimethylaminopyridine. Ph3P. I2 can also be used to reduce graphene oxide for the production of graphene nanosheets under mild and environmentally friendly conditions.

Technology Process of Diiodotriphenylphosphorane

There total 8 articles about Diiodotriphenylphosphorane 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: 100.0%

triphenylphosphine (603-35-0) → triphenylphosphine diiodide (6396-07-2)

Guidance literature:

With iodine; In diethyl ether; at 20 ℃; for 1h;

DOI:10.1002/cmdc.201600223

Reference yield: 86.0%

dibromotriphenylphosphorane (1034-39-5) → triphenylphosphine diiodide (6396-07-2)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1055/s-1980-29222

Reference yield:

triphenylphosphine (603-35-0) + tetraethylphosphorodiamidothioic iodide (93374-06-2) → tetraethylphosphorodiamidous iodide (59612-01-0) + triphenylphosphine diiodide (6396-07-2) + bis disulfide + triphenylphosphine sulfide (3878-45-3)

Guidance literature:

In benzene; for 1h; Yield given. Yields of byproduct given; Ambient temperature;

upstream raw materials:

pentaphenylphosphorane

triphenylphosphine

trimethylsilyl iodide

dichlorotriphenylphosphorane

Downstream raw materials:

manganese(II) iodide

MnI₂(P(C₆H₅)3)2

diiodobis(triphenylphosphine)zinc

zinc(II) iodide

Refernces

• 1、 -. "3-(1H-PYRAZOL-4-YL)PYRIDINE ALLOSTERIC MODULATORS OF M4 MUSCARINIC ACETYLCHOLINE RECEPTOR". Page/Page column 105. . Retrieved 2020/05/28.
• 2、 Sawatzky, Edgar,Al-Momani, Ehab,Kobayashi, Ryohei,Higuchi, Takahiro,Samnick, Samuel,Decker, Michael. "A Novel Way To Radiolabel Human Butyrylcholinesterase for Positron Emission Tomography through Irreversible Transfer of the Radiolabeled Moiety". . p. 1540 - 1550. Retrieved 2016/08/28.