13435-20-6

Basic information

• Product Name: TETRAETHYLAMMONIUM CYANIDE
• Synonyms: TETRAETHYLAMMONIUM CYANIDE;Ethanaminium, N,N,N-triethyl-, cyanide;Tetraethylaminium·cyanide;Tetraethylammonium cyanide purum, >=95% (AT);Tetraethylammonium cyanide 94%;EthanaMiniuM,N,N,N-triethyl-, hydrocyanic acid (1:1);tetraethylazanium,cyanide
• CAS NO: 13435-20-6
• Molecular Formula: CN*C₈H₂₀N
• Molecular Weight: 156.27
• EINECS: 236-566-2
• Product Categories: Ammonium Salts;Greener Alternatives: Catalysis;Phase Transfer Catalysts
• Mol File: 13435-20-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 250 °C (dec.)(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• BRN: 3570222
• CAS DataBase Reference: TETRAETHYLAMMONIUM CYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAETHYLAMMONIUM CYANIDE(13435-20-6)
• EPA Substance Registry System: TETRAETHYLAMMONIUM CYANIDE(13435-20-6)

Safety Data

• Hazard Codes: T+,N
• Statements: 26/27/28-32-50/53
• Safety Statements: 7-28-29-45-60-61
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• F: 3-8-10
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 13435-20-6(Hazardous Substances Data)

Usage

Uses

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.

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

Synthetic route

potassium cyanide + tetraethylammonium chloride (56-34-8) → tetraethylammoniumcyanide (13435-20-6)

Conditions	Yield
In water for 1h; Reflux;	79%

tetraethylammonium chloride (56-34-8) + NaCN → tetraethylammoniumcyanide (13435-20-6)

Conditions	Yield
In methanol	50.6%

2-isopropyliodobenzene (19099-54-8) + tetraethylammoniumcyanide (13435-20-6) + copper(I) cyanide (544-92-3) → 2-Isopropyl-1-benzonitrile (40751-52-8)

Conditions	Yield
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran for 1.5h; Heating / reflux;	100%

C15H23ClN4O4 (929016-41-1) + tetraethylammoniumcyanide (13435-20-6) → methyl 2-cyano-6-[2-{[(1,1-dimethylethyl)oxy]carbonyl}-1-(2-methylpropyl)hydrazino]-4-pyrimidinecarboxylate (929015-78-1)

Conditions	Yield
With trimethylamine In tetrahydrofuran at -78 - 20℃; for 24h;	100%

thorium di-π-cyclooctatetraene (12702-09-9) + tetraethylammoniumcyanide (13435-20-6) → CN(1-)*C8H20N(1+)*Th(4+)*2C8H8(2-)

Conditions	Yield
With pyridine for 15h; Reflux; Inert atmosphere;	100%

syn-[Mo2O2(μ-S)2(S2)(DMF)3] + tetraethylammoniumcyanide (13435-20-6) → C3Mo2N3O2S4(3-)*3C8H20N(1+)

Conditions	Yield
In acetonitrile at 0℃;	100%

dicarbonyl(cyclopentadienyl)(ethyl vinyl ether)iron tetrafluoroborate + tetraethylammoniumcyanide (13435-20-6) → 2-cyano-2-ethoxyethyldicarbonyl-η-cyclopentadienyliron(II)

Conditions	Yield
In dichloromethane byproducts: tetraethylammonium tetrafluoroborate; Et4NCN (5% xs) was added to a soln. of Fe-complex in CH2Cl2 under Ar at 0°C, mixt. was stirred for 0.5 h; ether was added, soln. was filtered through a short plug of alumina to remove Et4NBF4, evapd. in vacuo; elem. anal.;	99%

1,3-(μ-propanedithiolato)diironhexacarbonyl + tetraethylammoniumcyanide (13435-20-6) → 2N(C2H5)4(1+)*[Fe(CO)2CN]2SC3H6S(2-)*H2O=[N(C2H5)4]2[Fe(CO)2CN]2SC3H6S*H2O

Conditions	Yield
In acetonitrile room temp.; elem. anal.;	99%

Mo2O5(O2C6H2(NCHC6H3(OC2H5)O)2Ni)2 + tetraethylammoniumcyanide (13435-20-6) → 2N(C2H5)4(1+)*2MoO2(2+)*O(2-)*2Ni(2+)*2CN(1-)*2O2C6H2(NCHC6H3(OC2H5)O)2(3-)=[N(C2H5)4]2[((CN)Ni(C24H20N2O6)MoO2)2O]

Conditions	Yield
In nitromethane; dichloromethane inert atmosphere; 2 equiv. Et4NCN, stirring in CH2Cl2/MeNO2=1:1 for 1 h (dissoln.); filtration, crystn. on layering with Et2O (overnight), collection (filtration; elem. anal.;	99%

tris(bis(trimethylsilylamido))cerium(III) (41836-21-9) + tetraethylammoniumcyanide (13435-20-6) → C19H54CeN4Si6(1-)*C8H20N(1+)

Conditions	Yield
In toluene at -78 - 20℃; for 6h; Inert atmosphere;	99%

(4R,9AR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (577712-02-8) + dppf + tetraethylammoniumcyanide (13435-20-6) → (4R,9AR)-6-cyano-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (577712-23-3)

Conditions	Yield
tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane	98.4%

tetraethylammoniumcyanide (13435-20-6) + 4-Chloromethyl-1-(4-chloro-phenyl)-5-pyrrol-1-yl-1H-pyrazole (116834-13-0) → 2-[1-(4-chlorophenyl)-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]acetonitrile (116834-15-2)

Conditions	Yield
In acetonitrile for 3h; Ambient temperature;	98%

tetraethylammoniumcyanide (13435-20-6) + Trifluoro-methanesulfonic acid 3-(tert-butyl-dimethyl-silanyloxymethyl)-3,4-dichloro-pent-4-enyl ester (214344-79-3) → 3-Chloro-3-(1-chloro-vinyl)-tetrahydro-furan

Conditions	Yield
	98%

C5H5Fe(CO)2((CHCH3)2OCHCHO) (101224-91-3) + tetraethylammoniumcyanide (13435-20-6) → {(2R,3R,5R,6R)-3-cyano-5,6-dimethyl-1,4-dioxan-2-yl}dicarbonyl(η5-cyclopentadienyl)iron(II) (101225-00-7)

Conditions	Yield
In not given identified by NMR spectra and single crystal X-ray anal.;	98%

{(C5H5)Re(NO)(P(C6H5)3)(((CH3)3SiCH2)2NC9H9)}(1+)*OSO2CF3(1-)={(C5H5)Re(NO)(P(C6H5)3)(((CH3)3SiCH2)2NC9H9)}OSO2CF3 + tetraethylammoniumcyanide (13435-20-6) → [(η(5)-C5H5)Re(NO)(PPh3)(CN)]

Conditions	Yield
With NaBH4 In methanol; dichloromethane byproducts: 1,4-(Me3SiCH2)2-1,2,3,4-tetrahydroisoquinoline; Et4NCN added to the complex in CH2Cl2, stirred for 1 h; solvent was removed under vac., chromy. on silica gel, evapd., addn. of ether/hexane, filtered, washed with hexane, dried under vac.;	98%

tetraethylammoniumcyanide (13435-20-6) + copper(l) cyanide + mercury(II) cyanide (592-04-1) → tetraethylammonium copper tetracyanomercurate

Conditions	Yield
In methanol suspending CuCN in abs. methanol under Ar, addn. of NEt4CN and Hg(CN)2,stirring 4 h at room temp.;; centrifugation, drying in a stream of Ar; elem. anal.;;	98%
In ethanol

[9,9-(CN-t-Bu)2-arachno-9,6-PtCB8H12] (1022920-08-6) + tetraethylammoniumcyanide (13435-20-6) → [NEt4]2[9,9-(CN)2-arachno-9,6-PtCB8H12]

Conditions	Yield
In dichloromethane (N2); Schlenk technique; Et4NCN (2 equiv.) was added to soln. of Pt complex in CH2Cl2; reacted at ambient temp. for 4 h; evapd. (vac.); washed (petroleum ether); dried (vac.); elem. anal.;	98%

3-chlorobenzo[e][1,2,4]triazine (91669-21-5) + tetraethylammoniumcyanide (13435-20-6) → benzo[e][1,2,4] triazine-3-carbonitrile

Conditions	Yield
In acetonitrile at 20℃; for 0.333333h;	98%

tetraethylammoniumcyanide (13435-20-6) + (3,3-Dimethyl-2-norbornyl)-methylbromid (66879-54-7, 105453-60-9, 105453-61-0, 109668-79-3) → Isocamphenilanylacetonitril (101372-39-8, 113104-71-5)

Conditions	Yield
In acetonitrile at 50℃; for 48h;	97%

tetraethylammoniumcyanide (13435-20-6) + ethenetetracarbonitrile (670-54-2) → {N(C2H5)4}(1+)*C6N4(1-)={N(C2H5)4}C6N4

Conditions	Yield
In acetonitrile at room temp.;	97%
In acetonitrile at room temp.;	97%

tetraethylammoniumcyanide (13435-20-6) + mercury(II) cyanide (592-04-1) → tetraethylammonium sodium tetracyanomercurate

Conditions	Yield
With NaCN In methanol dissolving of NEt4CN and Hg(CN)2 under Ar in abs. methanol, addn. of NaCN, stirring 30 min at room temp., addn. of diethyl ether;; filtration, repeated washing with methanol, drying at 60°C; elem. anal.;;	97%
With NaCN In ethanol ethanolic solns. of NEt4CN; Hg(CN)2, and NaCN were mixed under argon;; ppt.;;

[Ru(C6H2(C(CH3)3)2S2CH2CH2)2S]2*C4H8O + tetraethylammoniumcyanide (13435-20-6) → meso-(NEt4)[Ru(CN)(C6H2(tBu)2S2CH2CH2)2S] (172088-49-2)

Conditions	Yield
In tetrahydrofuran; methanol N2 atm.; THF/MeOH 3/1 ratio, refluxing (2 h); concn., filtn., washing (hexane), drying (vac., 1 d); elem. anal.;	97%

3-cyano-3-(1-oxo-2-azaspiro[5.5]undecan-7-yl)propyl methanesulfonate + tetraethylammoniumcyanide (13435-20-6) → 2-(1-oxo-2-azaspiro[5.5]undecan-7-yl)pentanedinitrile

Conditions	Yield
In acetonitrile at 60℃; for 12h; Molecular sieve; Inert atmosphere;	97%

tetraethylammoniumcyanide (13435-20-6) + 4-Chloromethyl-1-(4-methoxy-phenyl)-5-pyrrol-1-yl-1H-pyrazole (116834-14-1) → [1-(4-Methoxy-phenyl)-5-pyrrol-1-yl-1H-pyrazol-4-yl]-acetonitrile (116834-16-3)

Conditions	Yield
In acetonitrile for 3h; Ambient temperature;	96%

tetraethylammoniumcyanide (13435-20-6) + 4-(4-methylphenyl)sulfonylbenzo[h]quinoline → benzo[h]quinoline-4-carbonitrile (860565-30-6)

Conditions	Yield
	96%

10-(phenyliodonium)-closo-1-monocarbadecaborate + tetraethylammoniumcyanide (13435-20-6) → C8H20N(1+)*C2H9B9N(1-)

Conditions	Yield
In acetonitrile at 20℃; for 7h;	96%

[cis-4-(8-chloro-2-cyclobutyl-1H-imidazo[4,5-c]quinolin-1-yl)tetrahydro-2H-pyran-2-yl]methyl methanesulfonate + tetraethylammoniumcyanide (13435-20-6) → [cis-4-(8-chloro-2-cyclobutyl-1H-imidazo[4,5-c]quinolin-1-yl)tetrahydro-2H-pyran-2-yl]acetonitrile

Conditions	Yield
In dimethyl sulfoxide at 80℃; for 16h;	96%

Me4N{VFe3S4((1,3,5-tris(4,6-dimethyl-3-mercaptophenyl)thio)-2,4,6-tris(p-tolylthio)benzenate)(DMF)3} + tetraethylammoniumcyanide (13435-20-6) → Me4N(EtN)3{VFe3S4((1,3,5-tris(4,6-dimethyl-3-mercaptophenyl)thio)-2,4,6-tris(p-tolylthio)benzenate)(CN)3}

Conditions	Yield
In N,N-dimethyl-formamide (N2); soln. of 0.384 mmol cyanide was added to soln. of 0.063 mmol Fe-V complex, pptn. formed within 5 min, mixt. was stirred for 30 min; solid filtered off, washed with small amts. of DMF, then with ether and dried in vac.;	95%

tetraethylammoniumcyanide (13435-20-6) + C26H31BrO6 (86943-53-5) → C27H31NO6 (86953-26-6)

Conditions	Yield
	94%

5,7-dichloro-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine (214707-02-5) + tetraethylammoniumcyanide (13435-20-6) → 7-cyano-5-chloro-6-(2,4,6-trifluorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine (882182-12-9)

Conditions	Yield
In acetonitrile at 0 - 20℃; for 3.25h;	94%

dicarbonyl(η5-cyclopentadienyl)(η-(5R,6R)-5,6-dimethyl-5,6-dihydrodioxin)iron(II) tetrafluoroborate (110772-33-3) + tetraethylammoniumcyanide (13435-20-6) → {(2R,3R,5R,6R)-3-cyano-5,6-dimethyl-1,4-dioxan-2-yl}dicarbonyl(η5-cyclopentadienyl)iron(II) (101225-00-7) + N,N,N,N-tetraethylammonium tetrafluoroborate (429-06-1)

Conditions	Yield
In dichloromethane Fp(dimethyldioxene)(BF4), Et4NCN and CH2Cl2 are combined at 0°C under Ar, stirring (0.5 h).; Addn. of ether pptd. Et4NBF4. Filtration of mixt. through Al2O3, washing of Al2O3 with ether, evapn. of solvents in vac., elem. anal.;	A 94% B n/a

{Ni(bis(2-mercaptoethyl)(2-(methylthio)ethyl)amine)}2 + tetraethylammoniumcyanide (13435-20-6) → (C2H5)4N(1+)*{Ni(CN)(SCH2CH2)2NCH2CH2SCH3}(1-)={(C2H5)4N}{Ni(CN)(SCH2CH2)2NCH2CH2SCH3}

Conditions	Yield
In N,N-dimethyl-formamide N2 atmosphere; addn. of Et4NCN in DMF to soln. of Ni-complex (molar ratio Et4NCN/Ni-complex 0.37:0.19), stirring (0.5 h); crystn. on toluene addn. and cooling (-20°C, several days), filtration off, washing (Et2O), drying (vac.); elem. anal.;	94%

Upstream product

• 56-34-8 tetraethylammonium chloride 

Downstream Products

• 108-94-1 cyclohexanone 
• 766-05-2 cyclohexane carbonitrile 
• 108-93-0 cyclohexanol 
• 126422-69-3 4-cyano-N-methyl-N-(2,2,2-trifluoroethyl)aniline 
• 126422-68-2 2-cyano-N-methyl-N-(2,2,2-trifluoroethyl)aniline 
• 126422-67-1 N-(cyanomethyl)-N-(2,2,2-trifluoroethyl)aniline 
• 126422-70-6 4,4'-bisbiphenyl 
• 253791-06-9 p-methylphenylacetonitrile-α-d₂ 
• 1699-39-4 2-(3-(benzyloxy)-4-methoxyphenyl)acetonitrile 
• 21288-34-6 2-(3-benzoylphenyl)acetonitrile 
• 773149-29-4 5-cyano-7-(2,5-dimethyl-2,5-dihydro-pyrrol-1-yl)-6-(2,4,6-trifluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyrimidine 
• 412031-32-4 dimethyl 4-cyano-1,3-benzenedicarboxylate 
• 139995-83-8 α-methoxyimino-2-phenoxyphenylacetonitrile 
• 924642-68-2 5-chloro-2-(morpholine-4-carbonyl)benzonitrile 

Relevant articles and documents

Chiral Crystals of an Achiral Molecule Exhibit Plastic Bending and a Crystal-to-Crystal Phase Transition

The achiral molecule 2-cyano-4,6-dimethylpyrimidine (Me2pmCN) meets simple criteria that predict a supramolecular arrangement capable of exhibiting plastic bending. Indeed, crystals grown by sublimation bend readily without breaking under manua