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| | 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) |
| | Dess-Martin periodinane Usage And Synthesis |
| 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 | | 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
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| | Dess-Martin periodinane Preparation Products And Raw materials |
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