tert-Butoxy bis(dimethylamino)methane , 90% , 5815-08-7

Synonym(s):
Bredereck’s reagent

CAS NO.：5815-08-7

Empirical Formula: C9H22N2O

Molecular Weight: 174.28

MDL number: MFCD00042858

EINECS: 227-383-9

PRODUCT Properties

• Boiling point: 50-55 °C/15 mmHg (lit.)
• Density: 0.844 g/mL at 25 °C (lit.)
• refractive index: n20/D 1.422(lit.)
• Flash point: 106 °F
• storage temp.: Sealed in dry,Store in freezer, under -20°C
• solubility: Chloroform (Sparingly), DMSO (Sparingly), Methanol (Slightly)
• pka: 5.46±0.38(Predicted)
• form: Liquid
• color: Clear pale yellow
• Specific Gravity: 0.844
• BRN: 1901973
• Stability: Hygroscopic
• InChI: InChI=1S/C9H22N2O/c1-9(2,3)12-8(10(4)5)11(6)7/h8H,1-7H3
• InChIKey: HXRAMSFGUAOAJR-UHFFFAOYSA-N
• SMILES: C(OC(C)(C)C)(N(C)C)N(C)C

Description and Uses

Bredereck's reagent, chemically known as tert-Butoxy bis(dimethylamino)methane, is a versatile reagent. It can be used for a-methylation, a-methylenation, and a-amidation of multiple carbonyl systems or compounds with active CH groups. The advantage is the in situ generation of strongly basic alkanes (t-BuO-) and the generation of the corresponding iminium ions by thermal decomposition. After the Mannich reaction of the carbonyl substrate with the in situ generated iminium ion, the dimethylamine is eliminated from the adduct B- in the final step to give the condensation product, which can be converted into various types of compounds.

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

• Symbol(GHS): GHS02,GHS07
• Signal word: Warning
• Hazard statements: H226-H315-H319-H335
• Precautionary statements: P210-P302+P352-P305+P351+P338
• Hazard Codes: Xi,F
• Risk Statements: 10-36/37/38
• Safety Statements: 26
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10
• HazardClass: 3
• PackingGroup: III
• HS Code: 29221990