''tert''-Butoxybis(dimethylamino)methane is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
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 react ...
. It is a colorless liquid with a amine odor.
Use as reagent
Also known as Bredereck's reagent, it is used for
formylation
In biochemistry, the addition of a formyl functional group is termed formylation. A formyl functional group consists of a carbonyl bonded to hydrogen. When attached to an R group, a formyl group is called an aldehyde.
Formylation has been identi ...
(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 roo ...
, 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 is an organic compound with the formula ( CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majo ...
(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 a ...
References
{{DEFAULTSORT:Butoxybis(dimethylamino)methane, tert-
Tertiary amines
Dimethylamino compounds
Tert-butyl compounds
Ethers