| Identification | More | [Name]
BREDERECK'S REAGENT | [CAS]
5815-08-7 | [Synonyms]
BREDERECKS REAGENT
BREDERECK'S REAGENT
BUTOXYBIS(DIMETHYLAMINO)METHANE
T-BUTOXYBIS(DIMETHYLAMINO)METHANE
TERT-BUTOXYBIS(DIMETHYLAMINO)METHANE
tert-Butoxybis(dimethylamino)methane, 85+%
Methanediamine, 1-(1,1-dimethylethoxy)-N,N,N,N-tetramethyl-
TERT-BUTOXY BIS(DIMETHYLAMINO)METHANE (BREDERECKS REAGENT)
tert-Butoxybis(dimethylamino)methane, tech.
Bis(dimethylamino)(tert-butoxy)methane
N,N,N',N'-Tetramethyl(tert-butoxy)methanediamine
N,N,N',N'-Tetramethyl-α-tert-butoxymethanediamine
α-(1,1-Dimethylethoxy)-N,N,N',N'-tetramethylmethanediamine
α-tert-Butoxy-N,N,N',N'-tetramethylmethanediamine | [EINECS(EC#)]
227-383-9 | [Molecular Formula]
C9H22N2O | [MDL Number]
MFCD00042858 | [Molecular Weight]
174.28 | [MOL File]
5815-08-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear pale yellow liquid | [Boiling point ]
50-55 °C/15 mmHg (lit.) | [density ]
0.844 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.422(lit.)
| [Fp ]
106 °F
| [storage temp. ]
Freezer (-20°C) | [solubility ]
Chloroform (Sparingly), DMSO (Sparingly), Methanol (Slightly) | [form ]
Liquid | [pka]
5.46±0.38(Predicted) | [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 | [CAS DataBase Reference]
5815-08-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [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 ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [F ]
10 | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29221990 |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
Clear pale yellow liquid | [Uses]
Mild enamination reagent; catalyst in ring-opening polymerization reactions. | [Uses]
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 |
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