[(tert-butoxy)(dimethylamino)methyl]dimethylamine

• ChemBase ID: 80974
• Molecular Formular: C9H22N2O
• Molecular Mass: 174.28378
• Monoisotopic Mass: 174.17321333
• SMILES: O(C(C)(C)C)C(N(C)C)N(C)C
• Canonical SMILES: CN(C(N(C)C)OC(C)(C)C)C
• InChI: InChI=1S/C9H22N2O/c1-9(2,3)12-8(10(4)5)11(6)7/h8H,1-7H3
• InChIKey: HXRAMSFGUAOAJR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(tert-butoxy)(dimethylamino)methyl]dimethylamine
• IUPAC Traditional name: [tert-butoxy(dimethylamino)methyl]dimethylamine
• Synonyms: Bredereck’s reagent; Bis(dimethylamino)(tert-butoxy)methane; 1-(tert-Butoxy)-N,N,N',N'-tetramethylmethanediamine; tert-Butoxy bis(dimethylamino)methane; 1-tert-Butoxy-N,N,N',N'-tetraMethylMethanediaMine; Bredereck 试剂; 叔丁氧基双(二甲胺基)甲烷

Database IDs

• CAS Number: 5815-08-7
• EC Number: 227-383-9
• MDL Number: MFCD00042858
• Beilstein Number: 1901973
• PubChem SID: 162068093; 24852244; 24863653
• PubChem CID: 79885

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.7030432
• LogD (pH = 7.4): 1.9249332
• Log P: 1.9286413
• Molar Refractivity: 53.0952 cm^3
• Polarizability: 21.058195 Å^3
• Polar Surface Area: 15.71 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 50-55 °C/15 mmHg(lit.); 50-55°C/15mm
• Flash Point: 105.8 °F; 41 °C; 41°C
• Density: 0.844; 0.844 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.422; n20/D 1.422(lit.)

Safety Information

• Storage Warning: Flammable/Irritant/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 10-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: 97%
• Grade: technical
• Linear Formula: (CH3)3COCH[N(CH3)2]2

DETAILS

Sigma Aldrich - 20425

Analysis Note
mixture of tert-Butoxy bis(dimethylamino)methane, tris(dimethylamino)methane and N,N-Dimethylformamide di-tert-butyl acetal
Other Notes
Review5; Mild condensation reactions6
Packaging
10, 50 mL in glass bottle
Application
Reactant for:
• Preparation of pyrroloquinazolines as photochemotherapeutic agents1
• Enanatioslective formal synthesis of the Cinchona alkaloid quinine via stereoselective intermolecular radical addition2
• Synthesis of camptothecin via intramolecular isomuenchnone cycloaddition reaction3
• Aminomethylenation reactions4

Sigma Aldrich - 384216

Application
Reagent for α-enamination of ketones and esters.5,6
Used for the enamination of active methylene and methyl groups.
Reactant for:
• Preparation of pyrroloquinazolines as photochemotherapeutic agents1
• Enanatioslective formal synthesis of the Cinchona alkaloid quinine via stereoselective intermolecular radical addition2
• Synthesis of camptothecin via intramolecular isomuenchnone cycloaddition reaction3
• Aminomethylenation reactions4
Packaging
1, 10 g in glass bottle