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Sigma-Aldrich

Tetraethylammonium bicarbonate

≥95.0% (T)

Synonym(s):

Tetraethylammonium hydrogen carbonate

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About This Item

Linear Formula:
(CH3CH2)4N(HCO3)
CAS Number:
17351-61-0
Molecular Weight:
191.27
MDL number:
MFCD08277046
UNSPSC Code:
12352116
PubChem Substance ID:
329749344
NACRES:
NA.22

Quality Level

100

assay

≥95.0% (T)

form

solid

SMILES string

OC([O-])=O.CC[N+](CC)(CC)CC

InChI

1S/C8H20N.CH2O3/c1-5-9(6-2,7-3)8-4;2-1(3)4/h5-8H2,1-4H3;(H2,2,3,4)/q+1;/p-1

InChI key

XUBMPLUQNSSFHO-UHFFFAOYSA-M

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Application

Tetraethylammonium bicarbonate is used:
  • In the synthesis of carbamate esters from amines.
  • As a precipitant for synthesizing Cu/ZnO catalysts via coprecipitation method.
  • As an alternative to the traditional phase-transfer system in [18F]radiofluorinations for preventing microreactor blockages.
  • To promote carboxylation of secondary carboxamides bearing a leaving group at the α-position in the synthesis of oxazolidine-2,4-diones.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetraethylammonium hydrogen carbonate in organic synthesis: Synthesis of oxazolidine-2, 4-diones.
Cesa S, et al.
Tetrahedron, 55(1), 193-200 (1999)
Ying Fu et al.
Journal of proteomics, 130, 108-119 (2015-09-19)
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A convenient method for the synthesis of carbamate esters from amines and tetraethylammonium hydrogen carbonate.
Inesi A, et al.
The Journal of Organic Chemistry, 63(4), 1337-1338 (1998)
Evaluation of tetraethylammonium bicarbonate as a phase-transfer agent in the formation of [18F] fluoroarenes.
Reed CD, et al.
Journal of Fluorine Chemistry, 143(4), 231-237 (2012)
Monica M Schroll et al.
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