tert-Butoxybis(dimethylamino)methane

tert-Butoxybis(dimethylamino)methane is an organic compound with the formula (CH3)3COCH(N(CH3)2)2. The compound is classified as an aminal ester, i.e. the tert-butyl alcohol derivative of the aminal bis(dimethylamino)methane. It is a colorless liquid with a amine odor.

tert-Butoxybis(dimethylamino)methane
Names
Other names
Bredereck's reagent
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.024.895
EC Number
  • 227-383-9
UNII
  • InChI=1S/C9H22N2O/c1-9(2,3)12-8(10(4)5)11(6)7/h8H,1-7H3
    Key: HXRAMSFGUAOAJR-UHFFFAOYSA-N
  • CC(C)(C)OC(N(C)C)N(C)C
Properties
C9H22N2O
Molar mass 174.288 g·mol−1
Appearance colorless liquid
Boiling point 128 °C (262 °F; 401 K)
Hazards
GHS labelling:
Warning
H226, H315, H319, H335
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, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Use as reagent

Also known as Bredereck's reagent, it is used for formylation (introduction of the CHO group).[1] Protonation releases tert-butyl alcohol, giving tetramethylformamidinium, which displaces active C-H bonds:

(CH3)3COCH(N(CH3)2)2 + H+ → (CH3)3COH + [CH(N(CH3)2)2]+
[CH(N(CH3)2)2]+ + CH2Z2 → Z2CHCH(N(CH3)2)2 + H+

The resulting bis(dimethylamino)methyl derivative in turn releases dimethylamine to give an enamine, which hydrolyzes.

Z2CHCH(N(CH3)2)2 → Z2C=CHN(CH3)2 + HN(CH3)2
Z2C=CHN(CH3)2 + H2O → Z2CHCHO + HN(CH3)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 (DMF) with dimethylcarbamoyl chloride[2]

References
  1. Kantlehner, Willi; Bowers, Albert (2007). "T-Butoxybis(dimethylamino)methane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rb350.pub2. ISBN 978-0471936237.
  2. Arnold, Z. (1959). "The preparation of tetramethylformamidinium salts and their vinylogues". Collection of Czechoslovak Chemical Communications. 24 (3): 760–765. doi:10.1135/cccc19590760.
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