274623

Dess-Martin periodinane

97%

• Sinônimo(s): 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one
• Fórmula empírica (Notação de Hill): C₁₃H₁₃IO₈
• Número CAS: 87413-09-0
• Peso molecular: 424.14
• Número MDL: MFCD00130127
• Código UNSPSC: 12352005
• ID de substância PubChem: 24856593
• NACRES: NA.22

Propriedades

• Nível de qualidade: 100
• Ensaio: 97%
• adequação da reação: reagent type: oxidant
• pf: 130-133 °C (lit.)
• temperatura de armazenamento: −20°C
• cadeia de caracteres SMILES: CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc12
• 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
• chave InChI: NKLCNNUWBJBICK-UHFFFAOYSA-N

Descrição

Descrição geral

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.

Aplicação

Dess–Martin periodinane is used as an oxidizing agent:

• For 1° and 2° alcohols to aldehydes and ketones.
• In the synthesis of N-protected α-amino aldehydes from the corresponding N-protected β-amino alcohols.
• To synthesize alkynyl oxoaldehyde probe (AlkMGO).

Used for the oxidation of hydroxychlorins to chlorin-α-diones and tetraones.

Características e benefícios

Benefits of using 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

Informações de segurança

• Pictogramas: GHS02,GHS07
• Palavra indicadora: Danger
• Frases de perigo: H242,H315,H319,H335
• Declarações de precaução: P210 - P235 - P302 + P352 - P305 + P351 + P338 - P370 + P378 - P403 + P233
• Classificações de perigo: Eye Irrit. 2 - Self-react. C - Skin Irrit. 2 - STOT SE 3
• Órgãos-alvo: Respiratory system
• Perigos de suplementos: EUH044
• Código de classe de armazenamento: 5.2 - Organic peroxides and self-reacting hazardous materials
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: dust mask type N95 (US), Eyeshields, Gloves