384216

tert-Butoxy bis(dimethylamino)methane

• Synonym(s): Bredereck’s reagent
• Linear Formula: (CH₃)₃COCH[N(CH₃)₂]₂
• CAS Number: 5815-08-7
• Molecular Weight: 174.28
• Beilstein: 1901973
• EC Number: 227-383-9
• MDL number: MFCD00042858
• UNSPSC Code: 12352100
• PubChem Substance ID: 24863653
• NACRES: NA.22

Properties

• form: liquid
• refractive index: n20/D 1.422 (lit.)
• bp: 50-55 °C/15 mmHg (lit.)
• density: 0.844 g/mL at 25 °C (lit.)
• 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
• InChI key: HXRAMSFGUAOAJR-UHFFFAOYSA-N

Description

Application

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

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

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

Safety Information

• Pictograms: GHS02,GHS07
• Signal Word: Warning
• Hazard Statements: H226,H315,H319,H335
• Precautionary Statements: P210 - P233 - P240 - P241 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 105.8 °F - closed cup
• Flash Point(C): 41 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves