1,1-bis(acetyloxy)-3-oxo-3H-1$l^{5},2-benziodaoxol-1-yl acetate

• ChemBase ID: 70652
• Molecular Formular: C13H13IO8
• Molecular Mass: 424.14199
• Monoisotopic Mass: 423.96551538
• SMILES: [I]1(OC(=O)c2c1cccc2)(OC(=O)C)(OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[I]1(OC(=O)C)(OC(=O)C)OC(=O)c2c1cccc2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,1-bis(acetyloxy)-3-oxo-3H-1$l^{5},2-benziodaoxol-1-yl acetate; 1,1-bis(acetyloxy)-3-oxo-3H-1λ^5,2-benziodaoxol-1-yl acetate
• IUPAC Traditional name: dess-martin periodinane; dess–martin periodinane
• Synonyms: 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one; Dess–Martin periodinane; Dess–Martin periodinane; 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one; Dess-Martin periodinane; DMP; 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one; Dess-Martin periodinane solution; 1,1-Dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one; Dess-Martin periodinane; 1,1,1-三(乙酰氧基)-1,1-二氢-1,2-苯碘酰-3-(1H)-酮; 戴斯-马丁氧化剂; 戴斯-马丁试剂; 戴斯-马丁氧化剂 溶液

Database IDs

• CAS Number: 87413-09-0
• MDL Number: MFCD00130127
• Beilstein Number: 4548207
• Merck Index: 142933
• PubChem SID: 162036367; 24879825; 24856593
• PubChem CID: 159087
• Chemspider ID: 139925
• Wikipedia Title: Dess–Martin_periodinane

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.898416
• LogD (pH = 7.4): 1.898416
• Log P: 1.898416
• Molar Refractivity: 80.292 cm^3
• Polarizability: 33.54322 Å^3
• Polar Surface Area: 105.2 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white powder, chips,; crystals or crystalline; powder and/or chunks
• Melting Point: 103 – 133 °C; 130-132°C dec.; 130-133 °C(lit.); 130-133°C
• Boiling Point: 40 °C
• Density: 1.362 g/cm^3 solid; 1.369 g/mL at 25 °C

Safety Information

• Storage Warning: IRRITANT; Moisture & Light Sensitive; Oxidising Agent/Harmful/Irritant/Air Sensitive/Moisture Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Oxidising (O); Irritant (Xi); Harmful (Xn)
• UN Number: 1593; UN1479
• German water hazard class: 3
• Hazard Class: 5.1; 6.1
• Packing Group: 3; III
• Risk Statements: 40-44; 8-20/21/22-36/37/38-44; 8-36/37/38-44
• Safety Statements: 17-26-37; 26-36; 36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS03; GHS06; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H272-H302-H312-H315-H319-H332-H335; H272-H315-H319-H335; H315-H319-H331-H351
• GHS Precautionary statements: P220-P261-P280-P305 + P351 + P338; P221-P210-P305+P351+P338-P302+P352-P405-P501A; P261-P281-P305 + P351 + P338-P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1593 6.1/PG 3
• Supplemental Hazard Statements: Risk of explosion if heated under confinement.
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: 95+%; 97%; 98%
• Concentration: 0.3 M in methylene chloride
• Empirical Formula (Hill Notation): C13H13IO8

DETAILS

Sigma Aldrich - 274623

Application
Oxidizing agent for 1° and 2° alcohols to aldehydes and ketones.1,2
Used for the oxidation of hydroxychlorins to chlorin-α-diones and tetraones.
Packaging
1, 5, 25, 50, 250 g in glass bottle

Sigma Aldrich - 559873

Application
Widely used reagent for the mild oxidation of alcohols to aldehydes and ketones.1
Packaging
5, 25 mL in glass bottle

REFERENCES

• One of the mildest reagents for the selective oxidation of primary and secondary alcohols to aldehydes and ketones. High yields can be obtained at ambient temperatures, under neutral conditions, in chloroform, dichloromethane or acetonitrile: J. Org. Chem., 48, 4155 (1983); J. Am. Chem. Soc., 113, 7277 (1991); (reviews): J. Prakt. Chem./Chem. Ztg., 338, 588 (1996); Synlett, 278 (2000). Has been employed for the oxidation of a wide variety of sensitive substrates and is particularly valuable in multi-step syntheses of polyfunctional molecules with complex stereochemistry. For an example involving exclusive oxidation of one of four possible secondary OH groups in a synthesis of erythromycin B, see: J. Am. Chem. Soc., 119, 3193 (1997). Allylic and benzylic alcohols can be oxidized selectively in the presence of saturated alcohols, and give the carbonyl compounds cleanly without over-oxidation or cis-trans isomerization: Tetrahedron Lett., 29, 995 (1988); J. Org. Chem., 55, 1636 (1990).
• CAUTION! In the presence of moisture, may form iodoxybenzoic acid which has been reported to be explosive under excessive heating or impact: Chem. Eng. News, 68(29), 3 (1990).
• For a detailed discussion of the scope and advantages of this reagent, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 7, p. 4982.
• Hydroxamic acids are oxidized to acyl nitroso compounds which can undergo cycloaddition to dienes: Synth. Commun., 30, 47 (2000).
• Has also been used for deoximation of ketoximes to ketones under mild conditions: Tetrahedron Lett., 39, 3209 (1998); Synthesis, 760 (1999).
• For use in the synthesis of imides, N-acyl vinylogous carbamates and ureas, and nitriles, by oxidation of amides and amines, see: Angew. Chem. Int. Ed., 44, 5992 (2005).
• Deprotection of thioacetals can be accomplished under extremely mild conditions: Org. Lett., 5, 575 (2003).
• ɑ,?-Unsaturated carboxylic acids undergo Hunsdiecker-type decaboxylative bromination with tetraethylammonium bromide in the presence of the reagent: Synlett, 2495 (2005).