384216

tert.-Butyloxy-bis-(dimethylamino)-methan

• Synonym(e): Bis-(dimethylamino)-tert.-butyloxymethan
• Lineare Formel: (CH₃)₃COCH[N(CH₃)₂]₂
• CAS-Nummer: 5815-08-7
• Molekulargewicht: 174.28
• Beilstein: 1901973
• EG-Nummer: 227-383-9
• MDL-Nummer: MFCD00042858
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24863653
• NACRES: NA.22

Eigenschaften

• Form: liquid
• Qualitätsniveau: 200
• Brechungsindex: n20/D 1.422 (lit.)
• bp: 50-55 °C/15 mmHg (lit.)
• Dichte: 0.844 g/mL at 25 °C (lit.)
• Funktionelle Gruppe: amine; ether
• SMILES String: CN(C)C(OC(C)(C)C)N(C)C
• InChI: 1S/C9H22N2O/c1-9(2,3)12-8(10(4)5)11(6)7/h8H,1-7H3
• InChIKey: HXRAMSFGUAOAJR-UHFFFAOYSA-N

Beschreibung

Anwendung

tert-Butoxy bis(dimethylamino)methane (Bredereck′s reagent) may be used in the following studies:

• Enamination of active methylene and methyl groups.[1][2]
• As condensation reagent in the synthesis of benz[c,d]indoles.[3]
• Preparation of methyl and ethyl 3-dimethylamino-2-(indol-3-yl)propenoate.[4]
• Synthesis of the macrolide natural product (-)-gloeosporone.[5]
• Preparation of new bioactive naphthyridine alkaloids lophocladine A and B.[6]
• Preparation of (E/Z)-ethyl 6,7-dichloro-3-[1-cyano-2-(dimethylamino)vinyl]-1-methyl-1H-indole-2-carboxylate.[7]
• Preparation of (E)-ethyl 3-(dimethylamino)-2-(1H-indol-3-yl)acrylate.[8]
• α-Enamination of ketones and esters.[9][10]

Reactant for:

• Preparation of pyrroloquinazolines as photochemotherapeutic agents
• Enanatioslective formal synthesis of the Cinchona alkaloid quinine via stereoselective intermolecular radical addition
• Synthesis of camptothecin via intramolecular isomuenchnone cycloaddition reaction
• Aminomethylenation reactions

Sicherheitshinweise

• Piktogramme: GHS02,GHS07
• Signalwort: Warning
• H-Sätze: H226,H315,H319,H335
• P-Sätze: P210 - P233 - P240 - P241 - P303 + P361 + P353 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 3 - Flammable liquids
• WGK: WGK 3
• Flammpunkt (°F): 105.8 °F - closed cup
• Flammpunkt (°C): 41 °C - closed cup
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter