tert-Butoxy bis(dimethylamino)methane
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tert-Butoxy bis(dimethylamino)methane
structure -
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CAS No:
5815-08-7
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Formula:
C9H22N2O
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Chemical Name:
tert-Butoxy bis(dimethylamino)methane
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Synonyms:
tert-Butoxy bis(dimethylamino)methane technical;T-BUTOXYBIS(DIMETHYLAMINO)METHANE;TERT-BUTOXYBIS(DIMETHYLAMINO)METHANE;BREDERECKS REAGENT;BUTOXYBIS(DIMETHYLAMINO)METHANE;tert-Butoxybis(dimethylamino)methane, 85+%;Bis(dimethylamino)(tert-butoxy)methane;N,N,N',N'-Tetramethyl(tert-butoxy)methanediamine
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CAS No:
Description
Clear pale yellow liquid
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.
tert-Butoxy bis(dimethylamino)methane Basic Attributes
174.28
174.28
1901973
227-383-9
JEJ0U558F7
DTXSID00206888
Clear pale yellow
29221990
Characteristics
15.7
1.4
Clear pale yellow Liquid
0.844 g/mL at 25 °C (lit.)
50-55 °C/15 mmHg (lit.)
106 °F
n20/D1.422(lit.)
Freezer (-20°C)
5.46±0.38(Predicted)
Sealed in dry,Store in freezer, under -20°C
Safety Information
III
3
UN 1993 3/PG 3
3
Xi,F
26
Xi,F
P261-P305 + P351 + P338
10-36/37/38
UN 1993 3/PG 3
|Warning|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 63 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
tert-Butoxy bis(dimethylamino)methane Use and Manufacturing
Mild enamination reagent; catalyst in ring-opening polymerization reactions.
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
Computed Properties
Molecular Weight:174.28
XLogP3:1.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:174.173213330
Monoisotopic Mass:174.173213330
Topological Polar Surface Area:15.7
Heavy Atom Count:12
Complexity:119
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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tert-Butoxy bis(dimethylamino)methane
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