358711

Tetraethylammonium cyanide

94%

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

Properties

• 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

Description

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.[1]
• Along with diethylazodicarboxylate (DEAD) in the regioselective C- or N- ethoxy-carbonylation of heterocyclic systems like indoles and indazoles.[2]
• In the synthesis of C-C-bridged bis-isoflavones from 2-bromomethyl-7,4′-dimethoxyisoflavone.[3]

Tetraethylammonium cyanide is a versatile reagent commonly used in cyanation reactions as cyanide source.[4][5][6] It is also used in the preparation of various cyanometalate complexes.[7][8]

Safety Information

• pictograms: GHS06,GHS09
• signalword: Danger
• hcodes: H300 + H310 + H330,H410
• pcodes: P262 - P264 - P273 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• 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_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges