Dess-Martin periodinane

Base Information

• Chemical Name: Dess-Martin periodinane
• CAS No.: 87413-09-0
• Molecular Formula: C13H13IO8
• Molecular Weight: 424.146
• Hs Code.: 29349990
• European Community (EC) Number: 672-328-8
• UNII: 336B74JK56
• DSSTox Substance ID: DTXSID30236335
• Nikkaji Number: J350.467K
• Wikipedia: Dess%E2%80%93Martin_periodinane
• Wikidata: Q420909
• ChEMBL ID: CHEMBL116656
• Mol file: 87413-09-0.mol

Synonyms:1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one;Dess-Martin periodinane

Chemical Property of Dess-Martin periodinane

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 130-133 °C
• Boiling Point: 40 °C
• Flash Point: >221 °F
• PSA: 105.20000
• Density: 1.369 g/mL at 25 °C
• LogP: 1.95370
• Storage Temp.: 0-6°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in chloroform, acetone, acetonitrile and methylene chlor
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 423.96551
• Heavy Atom Count: 22
• Complexity: 499

Purity/Quality:

99.9% ^*data from raw suppliers

Dess-MartinPeriodinane(TechnicalGrade) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, O, Xi
• Hazard Codes: Xn,O,Xi
• Statements: 22-36/37/38-40-8-20/21/22-44
• Safety Statements: 26-36-36/37-24/25-23-17-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OI1(C2=CC=CC=C2C(=O)O1)(OC(=O)C)OC(=O)C
• Uses: Dess-Martin Periodinaneis a very usefulreagent used in the oxidation of primary alcohols to aldehydes and secondary alcohols to ketones. Dess Martin periodinane is used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. It is also used as an oxidant for complexes with multifunctional alcohols. It is actively involved in the oxidation of N-protected-amino alcohols without epimerization and allylic alcohols.

Technology Process of Dess-Martin periodinane

There total 5 articles about Dess-Martin periodinane 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: 98.0%

acetic anhydride (108-24-7) + 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione (61717-82-6) → Dess-Martin periodane (87413-09-0)

Guidance literature:

With toluene-4-sulfonic acid; at 80 ℃; for 0.333333h;

Reference yield: 78.0%

acetic anhydride (108-24-7) + acetic acid (64-19-7,77671-22-8) + 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione (61717-82-6) → Dess-Martin periodane (87413-09-0)

Guidance literature:

1.) r.t. to 85 deg C, 1 h, 2.) 85 deg C, 1.3 h;

DOI:10.1021/jo00103a067

Reference yield: 65.0%

→ Dess-Martin periodane (87413-09-0)

Guidance literature:

upstream raw materials:

acetic anhydride

1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione

acetic acid

2-Iodobenzoic acid

Downstream raw materials:

2-acetoxytetrahydrofuran

oxepan-2-yl acetate

hexanedial

ethyl 2-bromoacetoacetate

Refernces

• 1、 -. "Process for preparing Dess-Martin reagent through solid superacid catalysis". Paragraph 0014; 0021; 0023; 0024; 0026; 0027; 0029; .... . Retrieved 2021/07/31.
• 2、 Sellami, Ines,Mall, Veronika,Schieberle, Peter. "Changes in the Key Odorants and Aroma Profiles of Hamlin and Valencia Orange Juices Not from Concentrate (NFC) during Chilled Storage". . p. 7428 - 7440. Retrieved 2018/06/19.