Dess-Martin periodinane CAS 87413-09-0
Dess-Martin periodinane Basic information
| Product Name: | Dess-Martin periodinane |
| Synonyms: | Dess-Martin periodinane,D M P, TAPI;dess-martin periodinate;1,1,1-Triacetoxy-1,2-benziodoxole-IV-3(1H)-one;1,1,1-Triacetoxy-1,3-dihydro-3-oxo-1,2-benziodoxole-IV;1,1,1-Triacetoxy-3H-1,2-benziodoxole-IV-3-one;Martin's reagent;1,1-Dihydro-1,1,1-triacetoxy-1,2-benzoiodooxol-3(1H)-one (Dess-M;Dess-Martin periodinane solution |
| CAS: | 87413-09-0 |
| MF: | C13H13IO8 |
| MW: | 424.14 |
| EINECS: | 672-328-8 |
| Product Categories: | Hypervalent Iodine;Synthetic Reagents;Hypervalent Iodine Compounds;Oxidation;Synthetic Organic Chemistry;Fused Ring Systems |
| Mol File: | 87413-09-0.mol |
Dess-Martin periodinane Chemical Properties
| Melting point | 130-133 °C (lit.) |
| Boiling point | 40 °C |
| density | 1.369 g/mL at 25 °C |
| Fp | >221 °F |
| storage temp. | -20°C |
| solubility | Soluble in chloroform, acetone, acetonitrile and methylene chloride. Slightly soluble in ether and hexane. |
| form | Liquid |
| color | Colorless to light yellow |
| Sensitive | Light Sensitive |
| Merck | 14,2933 |
| BRN | 4548207 |
| Stability: | Light Sensitive |
| InChI | InChI=1S/C13H13IO8/c1-8(15)19-14(20-9(2)16,21-10(3)17)12-7-5-4-6-11(12)13(18)22-14/h4-7H,1-3H3 |
| InChIKey | NKLCNNUWBJBICK-UHFFFAOYSA-N |
| SMILES | I1(OC(=O)C)(OC(=O)C)(OC(=O)C)OC(=O)C2C=CC=CC1=2 |
| CAS DataBase Reference | 87413-09-0(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn,O,Xi |
| Risk 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 |
| RIDADR | UN 1593 6.1/PG 3 |
| WGK Germany | 3 |
| Hazard Note | Harmful/Light sensitive |
| TSCA | No |
| HazardClass | 5.1 |
| PackingGroup | Ⅲ |
| HS Code | 29349990 |
| Storage Class | 5.2 - Organic peroxides and self-reacting hazardous materials |
| Hazard Classifications | Eye Irrit. 2 Self-react. C Skin Irrit. 2 STOT SE 3 |
| Description | Dess-Martin periodinane (DMP) is a hypervalent iodine compound widely used as a mild reagent for the oxidation of primary/secondary alcohols to aldehydes/ketones; oxidation of amides into imides; the dehydrogenation of amines to nitriles, and disulfides to sulfones. It is also used to selectively oxidize alkenes to epoxides. This is a useful reaction for generating three-membered cyclic ethers. Additionally, DMP is used to oxidatively cleave 1,2-diols to form aldehydes or ketones and in the synthesis of lactones. |
| Chemical Properties | White Crystalline powder |
| Uses | Dess-Martin Periodinaneis a very usefulreagent used in the oxidation of primary alcohols to aldehydes and secondary alcohols to ketones. |
| Uses | Oxidizing reagent. |
| Uses | 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. |
| reaction suitability | reagent type: oxidant |
| Synthesis | 2-Iodobenzoic acid (50.0 g,0.20 mol) was added to cyclobutanesulfone (250 mL), and the solution was heated to 50 ??C. 90% of the above solution was slowly added dropwise to an aqueous solution of potassium persulfate (147.4g,0.24mol,1.2eq) at 50??C (300mL) and the reaction was held for 3 hours. Subsequently, the reaction solution was heated to 95 ??C and the remaining 10% 2-iodobenzoic acid solution was slowly added dropwise to the reaction solution and the reaction was continued for 3 hours. Upon completion of the reaction, the reaction was cooled to 5 ??C and stirring was continued at this temperature for 1.5 hours. Under stirring, 1 L of water was added, filtered (the filtrate was to be recycled for set use), the filter cake was washed with water and acetone sequentially, and dried at room temperature for 16 hours to obtain 53.2 g of 2-iodobenzoic acid (yield 95.04%), white solid, with a purity of 99.7% (confirmed by NMR and HPLC). The solid was identified as 2-iodoacylbenzoic acid by HNMR. 2-Iodoacylbenzoic acid (45 g, 0.16 mol) was added to acetic anhydride (49 g, 0.48 mol) and dioxane (90 mL), followed by B(C6F5)3 (0.0016 mol) followed by B(C6F5)3 (0.0016 mol), and the reaction solution was heated to 50 ??C and stirred for 10 min, then the solvent was evaporated off by spin-drying under reduced pressure, and the reaction solution was added to methyl tert-butyl ether (400 mL). Filtered and dried at room temperature to obtain a white solid (61.1 g, yield: 90%). The purity of Desmartin oxidizer was 99.1% (confirmed by NMR). |
| Advantages | Benefits of using Dess-Martin periodinane (DMP) as an oxidizing reagent: milder reaction conditions (room temperature, neutral pH) shorter reaction times and higher yields high chemoselectivity tolerance of sensitive functional groups, and a long shelf life simplified workups |
Dess-Martin periodinane Preparation Products And Raw materials
| Raw materials | Acetic acid-->Acetic anhydride-->p-Toluenesulfonic acid-->Potassium bromate-->2-Iodobenzoic acid-->2-Iodoxybenzoic acid |
| Preparation Products | C-(3,4-DIHYDRO-2H-BENZO[1,4]OXAZIN-3-YL)-METHYLAMINE-->3-Chloro-4-Cyanobenzaldehyde-->3-(4-FLUORO-PHENYL)-1-ISOPROPYL-1H-INDOLE-2-CARBALDEHYDE-->(3-OXO-PROPYL)-CARBAMIC ACID TERT-BUTYL ESTER-->4-FORMYL-N-CBZ-PIPERIDINE-->1-[[(4-METHYLPHENYL)SULPHONYL]OXY]-1,2-BENZIODOXOL-3(1H)-ONE-->1H-Indazole-1-propanoic acid |
