87413-09-0
Dess-Martin periodinane
CAS: 87413-09-0
Molecular Formula: C13H13IO8
87413-09-0 - Names and Identifiers
| Name | Dess-Martin periodinane |
| Synonyms | Dess-martin Martin's reagent Dess-Martin Reagent Triacetoxyperiodinane dess-martin periodinate Dess Martin Periodinane Dess-Martin periodinane Dess-Martin periodinane solution Dess-Martin periodinane,D M P, TAPI 1,1,1-Triacetoxy-3H-1,2-benziodoxole-IV-3-one 1,1,1-Triacetoxy-1,2-benziodoxole-IV-3(1H)-one 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one 1,1,1-Triacetoxy-1,3-dihydro-3-oxo-1,2-benziodoxole-IV 1,1-Dihydro-1,1,1-triacetoxy-1,2-benzoiodooxol-3(1H)-one (1,1,1-Triacetoxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one 1,1,1-tris(acetyloxy)-1lambda~5~,2-benziodoxol-3(1H)-one 1,1-Dihydro-1,1,1-triacetoxy-1,2-benzoiodooxol-3(1H)-one (Dess-M |
| CAS | 87413-09-0 |
| EINECS | 672-328-8 |
| InChI | InChI=1/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 |
87413-09-0 - Physico-chemical Properties
| Molecular Formula | C13H13IO8 |
| Molar Mass | 424.14 |
| Density | 1.369g/mLat 25°C |
| Melting Point | 130-133 °C (lit.) |
| Boling Point | 40°C |
| Flash Point | >221°F |
| Solubility | Soluble in chloroform, acetone, acetonitrile and methylene chloride. Slightly soluble in ether and hexane. |
| Appearance | Solid |
| Color | Colorless to light yellow |
| Merck | 14,2933 |
| BRN | 4548207 |
| Storage Condition | -20°C |
| Sensitive | Light Sensitive |
| MDL | MFCD00130127 |
| Physical and Chemical Properties | Density: 1.362 |
| Use | Oxidant, used to oxidize hydroxyl dihydroporphyrin (hydroxychlorins) to produce dihydroporphyrin-α-diones (chlorin-α-diones) and tetraketones. It is also used to oxidize alcohols to aldehydes and ketones. |
87413-09-0 - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R40 - Limited evidence of a carcinogenic effect R8 - Contact with combustible material may cause fire R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R44 - Risk of explosion if heated under confinement |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S36/37 - Wear suitable protective clothing and gloves. S24/25 - Avoid contact with skin and eyes. S23 - Do not breathe vapour. S17 - Keep away from combustible material. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | UN 1593 6.1/PG 3 |
| WGK Germany | 3 |
| TSCA | No |
| HS Code | 29349990 |
| Hazard Note | Harmful/Light sensitive |
| Hazard Class | 5.1 |
| Packing Group | Ⅲ |
87413-09-0 - Reference Information
| Overview | dis Martin oxidant is white crystal, Melting Point: 130-133 ℃, dis Martin oxidant (also known as Dess-Martine high iodine reagent, referred to as DMP) is a commonly used, mild, and selective oxidation reagent. Often used for primary alcohol oxidation to aldehydes, secondary alcohol oxidation to ketones. Its advantages are mild reaction conditions, moderate speed, less dosage and simple post-treatment. |
| preparation | 2-iodobenzoic acid (50.0g,0.20mol) was added to sulfolane (250mL), the solution was heated to 50 °c. 90% of the above solution was slowly added dropwise to an aqueous solution (147.4 ml) of potassium hydrogen persulfate (0.24g, 1.2 mol, eq) at 50 ° C., and the reaction was incubated 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. After completion of the reaction, it was cooled to 5 °c and stirring was continued at this temperature for 1.5 hours. 1L of water was added with stirring and filtered (the filtrate was to be recycled). The filter cake was rinsed with water and acetone successively and dried at room temperature for 16 hours to obtain 53.2g of 2-iodoylbenzoic acid (yield: 95.04%), white solid with 99.7% purity (confirmed by NMR and HPLC). Detected by HNMR, The solid was determined to be 2-iodoylbenzoic acid. 2-iodoylbenzoic acid (45g,0.16mol) was added to acetic anhydride (49G, 0.48mol) and dioxane (90ml), followed by B(C6F5)3(0.0016mol), the reaction solution was heated to 50 ° C. And stirred for 10 minutes, and then the solvent was distilled off under reduced pressure. The reaction solution was added with methyl tert-butyl ether (400mL), suction filtered, and dried at room temperature to obtain a white solid (61.1g, yield: 90%). The purity of the DIS Martin oxidant was 99.1% (confirmed by NMR). |
| organic high iodine compounds | in recent years, organic high iodine compounds as a kind of easy preparation, mild performance, new Reagents for Organic Synthesis, which are highly selective and environmentally friendly, are widely used in modern organic synthesis. Dess-Martin iodine compounds (DMP) is one of the most studied and most widely used reagents. Deiss-Martin oxidant (also known as Dess-Martin high iodine reagent) is a commonly used, mild, and selective oxidation reagent. It is often used for the oxidation of primary alcohols to aldehydes and secondary alcohols to ketones. Its advantages are mild reaction conditions, moderate speed, less dosage and simple post-treatment. The preparation method can be prepared by the cheap O-iodobenzoic acid with potassium bromate in the appropriate concentration of sulfuric acid solution oxidation to form ring compound, the compound is then treated with acetic anhydride to obtain Dess-Martin periodinane reagent. |
| Application | important oxidation reagent mild oxidant, mostly used in total synthesis of natural products. oxidizing agents for the oxidation of 1 ° and 2 ° alcohols to aldehydes and ketones; for the oxidation of hydroxychlorophenols to dihydrochlorophenols-α-diketones and tetraketones for the oxidation of hydroxydihydroporphyrins dihydroporphyrin-α-diketones (chlorin-α-Diones) and tetraones were generated. It is also used for the oxidation of alcohols to aldehydes and ketones. |
Last Update：2024-04-09 19:05:15
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