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358711

Sigma-Aldrich

Tetraethylammonium cyanide

94%

Synonym(s):

N,N,N-triethyl-ethanaminium cyanide

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About This Item

Linear Formula:
(C2H5)4N(CN)
CAS Number:
Molecular Weight:
156.27
Beilstein/REAXYS Number:
3570222
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

94%

form

powder

mp

250 °C (dec.) (lit.)

SMILES string

[C-]#N.CC[N+](CC)(CC)CC

InChI

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

InChI key

PCZOZSATUTWXIC-UHFFFAOYSA-N

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Application

Tetraethylammonium cyanide can be used:
  • As a cyanide source for 1,4-addition of cyano group to enones (chalcones) catalyzed by scandium(III) triflate to yield β-cyanoketones.
  • Along with diethylazodicarboxylate (DEAD) in the regioselective C- or N- ethoxy-carbonylation of heterocyclic systems like indoles and indazoles.
  • In the synthesis of C-C-bridged bis-isoflavones from 2-bromomethyl-7,4′-dimethoxyisoflavone.

Tetraethylammonium cyanide is a versatile reagent commonly used in cyanation reactions as cyanide source. It is also used in the preparation of various cyanometalate complexes.

pictograms

Skull and crossbonesEnvironment

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Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1

supp_hazards

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


Certificates of Analysis (COA)

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Carbon Monoxide and Cyanide Ligands in a Classical Organometallic Complex Model for Fe?Only Hydrogenase.
Lyon E J, et al.
Angewandte Chemie (International Edition in English), 38(21), 3178-3180 (1999)
Nucleophilic aromatic substitution of hydrogen: a novel electrochemical approach to the cyanation of nitroarenes.
Gallardo I, et al.
Chemistry?A European Journal , 7(8), 1759-1765 (2001)
Tetraethylammonium Cyanide.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2009)
Synthesis of C- C-bridged bis-isoflavones
Al-Maharik NI, et al.
The Journal of Organic Chemistry, 65(8), 2305-2308 (2000)
Tetraethylammonium Cyanide.
e-EROS Encyclopedia of Reagents for Organic Synthesis (2009)

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