''tert''-Butoxybis(dimethylamino)methane is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula (CH
3)
3COCH(N(CH
3)
2)
2. The compound is classified as an
aminal
In organic chemistry, an aminal or aminoacetal is a functional group or type of organic compound that has two amine groups attached to the same carbon atom: . (As is customary in organic chemistry, R can represent hydrogen or an alkyl group). A ...
ester, i.e. the tert-butyl alcohol derivative of the aminal
bis(dimethylamino)methane
Bis(dimethylamino)methane is the organic compound with the formula CH3)2Nsub>2CH2. It is classified as an aminal as well as a ditertiary amine, in fact the simplest. It is a colorless liquid that is widely available. It is prepared by the reac ...
. It is a colorless liquid with a amine odor.
Use as reagent
Also known as Bredereck's reagent, it is used for
formylation
Formylation refers to any chemical processes in which a compound is functionalized with a formyl group (-CH=O). In organic chemistry, the term is most commonly used with regards to aromatic compounds (for example the conversion of benzene to benz ...
(introduction of the CHO group).
Protonation releases
tert-butyl alcohol
''tert''-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as ''t''-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. ''tert''-Butyl alcohol is a colorless solid, which melts near ...
, giving
tetramethylformamidinium, which displaces active C-H bonds:
:(CH
3)
3COCH(N(CH
3)
2)
2 + H
+ → (CH
3)
3COH +
H(N(CH3)2)2sup>+
:
H(N(CH3)2)2sup>+ + CH
2Z
2 → Z
2CHCH(N(CH
3)
2)
2 + H
+
The resulting bis(dimethylamino)methyl derivative in turn releases dimethylamine to give an enamine, which hydrolyzes.
:Z
2CHCH(N(CH
3)
2)
2 → Z
2C=CHN(CH
3)
2 + HN(CH
3)
2
:Z
2C=CHN(CH
3)
2 + H
2O → Z
2CHCHO + HN(CH
3)
2
Preparation
Tert-Butoxybis(dimethylamino)methane is obtained from tetramethylformamidinium chloride by reaction with tert-butoxide. Tetramethylformamidinium salts are obtained by the reaction of
dimethylformamide
Dimethylformamide, DMF is an organic compound with the chemical formula . Its structure is . Commonly abbreviated as DMF (although this initialism is sometimes used for 2,5-dimethylfuran, dimethylfuran, or dimethyl fumarate), this colourless liqui ...
(DMF) with
dimethylcarbamoyl chloride
Dimethylcarbamoyl chloride (DMCC) is a reagent for transferring a dimethylcarbamoyl group to alcoholic or phenolic hydroxyl groups forming dimethyl carbamates, usually having pharmacological or pesticidal activities. Because of its high toxicity ...
References
{{DEFAULTSORT:Butoxybis(dimethylamino)methane, tert-
Tertiary amines
Dimethylamino compounds
Tert-butyl compounds
Ethers