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358711

Tetraethylammonium cyanide

94%, powder

Synonym(s):

N,N,N-triethyl-ethanaminium cyanide

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About This Item

Linear Formula:
(C2H5)4N(CN)
CAS Number:
13435-20-6
Molecular Weight:
156.27
NACRES:
NA.22
PubChem Substance ID:
24861985
UNSPSC Code:
12352116
EC Number:
236-566-2
MDL number:
MFCD00066552
Beilstein/REAXYS Number:
3570222
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Product Name

Tetraethylammonium cyanide, 94%

Quality Level

200

assay

94%

form

powder

reaction suitability

core: ammonium

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

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

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH032

Storage Class

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL8443
BCCG4556
BCBD7180
BCBQ3930V
BCBD7180V

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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)
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)
Synthesis of C- C-bridged bis-isoflavones
Al-Maharik NI, et al.
The Journal of Organic Chemistry, 65(8), 2305-2308 (2000)
View All Related Papers

Global Trade Item Number

SKUGTIN
358711-25G04061833002353
358711-5G04061833002360