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358711

Sigma-Aldrich

Tetraethylammonium cyanide

94%

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Synonym(s):
N,N,N-triethyl-ethanaminium cyanide
Linear Formula:
(C2H5)4N(CN)
CAS Number:
13435-20-6
Molecular Weight:
156.27
Beilstein:
3570222
EC Number:
236-566-2
MDL number:
MFCD00066552
UNSPSC Code:
12352116
PubChem Substance ID:
24861985
NACRES:
NA.22

Quality Level

200

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
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H410

Hazard Classifications

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

Supplementary Hazards

EUH032

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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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)
An S= 2 cyanide-bridged trinuclear FeIII2NiII single-molecule magnet.
Li D, et al.
Inorganic Chemistry, 45(14), 5251-5253 (2006)
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)
Regioselective ethoxy-carbonylation of indoles and indazoles using DEAD and tetraethylammonium cyanide
Ramesh S, et al.
Royal Society of Chemistry Advances, 3(23), 8666-8669 (2013)
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