395315

Ethyldiazoacetoacetat

• Synonym(e): Ethyl Α-diazoacetoacetate, Ethyl 2-diazo-3-oxobutanoate
• Lineare Formel: CH₃COC(N₂)CO₂C₂H₅
• CAS-Nummer: 2009-97-4
• Molekulargewicht: 156.14
• MDL-Nummer: MFCD09039264
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24864652
• NACRES: NA.22

Eigenschaften

• Dampfdruck: 0.36 psi ( 20 °C)
• Form: liquid
• Verfügbarkeit: available only in USA
• Brechungsindex: n20/D 1.474 (lit.)
• Dichte: 1.131 g/mL at 25 °C (lit.)
• Funktionelle Gruppe: ester; ketone
• SMILES String: CCOC(=O)C(=[N+]=[N-])C(C)=O
• InChI: 1S/C6H8N2O3/c1-3-11-6(10)5(8-7)4(2)9/h3H2,1-2H3
• InChIKey: JWTPSIXYXYNAOU-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

Ethyl diazoacetoacetate is a diazo compound. It participates in Rh₂(OAc)₄-catalyzed reactions with arylalkylamines and diarylamines.[1] Reaction of ethyl diazoacetoacetate with N-methyl pyrrole and pyrrole derivatives has been studied.[2]

Anwendung

Ethyl diazoacetoacetate can be used as a reactant to synthesize:

• 1,4-oxathiocines and thiopyran derivatives via Rh-catalyzed reaction with 2-amino-4,5-dihydro-3-thiophenecarbonitriles.[3]
• β-keto esters via C−H insertion reaction with aromatic aldehydes using NbCl₅ as a catalyst.[4]
• Diazoacetoacetate derivatives by reacting with aldehydes via aldol condensation and subsequent and in situ oxidation reaction.[5]
• Isoquinolone and pyridone derivatives by Rh-catalyzed C−H activation/annulation reaction with various N-methoxybenzamides.[6]

Sicherheitshinweise

• Piktogramme: GHS02,GHS07
• Signalwort: Danger
• H-Sätze: H242,H315,H319,H335
• P-Sätze: P210 - P235 - P302 + P352 - P305 + P351 + P338 - P370 + P378 - P403 + P233
• Gefahreneinstufungen: Eye Irrit. 2 - Self-react. C - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 5.2 - Organic peroxides and self-reacting hazardous materials
• WGK: WGK 3
• Flammpunkt (°F): 185.0 °F - closed cup
• Flammpunkt (°C): 85 °C - closed cup
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves