151-50-8

Basic information

• Product Name: Potassium cyanide
• Synonyms: Potassiumcyanide (8CI);Cyanide of potassium;Hydrocyanic acid, potassium salt;Kalium cyanid;Potassium cyanide (K(CN))
• CAS NO: 151-50-8
• Molecular Formula: CKN
• Molecular Weight: 65.12
• EINECS: 205-792-3
• Mol File: 151-50-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 634 °C
• Boiling Point: 1625 °C
• Flash Point: 1625°C
• Appearance: White crystalline solid
• Density: 1.00 g/mL at 20 °C
• Water Solubility: Soluble in water
• CAS DataBase Reference: Potassium cyanide(CAS DataBase Reference)
• NIST Chemistry Reference: Potassium cyanide(151-50-8)
• EPA Substance Registry System: Potassium cyanide(151-50-8)

Safety Data

• RIDADR: 1680
• HazardClass: 6.1
• PackingGroup: I
• Hazardous Substances Data: 151-50-8(Hazardous Substances Data)

Usage

Chemical Description

Potassium cyanide is a highly toxic salt that is used in various chemical reactions.

InChI:InChI=1/CN.K/c1-2;/rCKN/c2-1-3

Synthetic route

hydrogen cyanide (74-90-8) + potassium ethoxide (917-58-8) → potassium cyanide (151-50-8)

hydrogen cyanide (74-90-8) → potassium cyanide (151-50-8)

Conditions	Yield
With potassium hydroxide; ethanol

potassium cyanate (590-28-3) → potassium cyanide (151-50-8)

Conditions	Yield
at 700℃;
at 900℃;

potassium thioacyanate (333-20-0) + sodium carbonate (497-19-8) → potassium cyanide (151-50-8)

9H-carbazole (86-74-8) + KOH → potassium cyanide (151-50-8)

Conditions	Yield
anschl. Gluehen;
anschl. Gluehen;

cyanuric acid (108-80-5) + potassium → potassium cyanide (151-50-8)

Conditions	Yield
Schmelzen mit viel Kalium;

N-(benzo[1,3]dioxol-5-yl-cyano-methyl)-glycin-ethyl ester + alcoholic KOH-solution → N-piperonylidene-glycine + potassium cyanide (151-50-8)

citrazinic acid (99-11-6) + potassium hydroxide → potassium cyanide (151-50-8) + oxalic acid (144-62-7)

Conditions	Yield
beim Schmelzen;

2,6-diethyl-5-methyl-3H-pyrimidin-4-one (859802-57-6) + potassium hydroxide → ammonia (7664-41-7) + potassium cyanide (151-50-8) + acetic acid (64-19-7) + propionic acid (802294-64-0)

Conditions	Yield
beim Schmelzen;

uric Acid (69-93-2) + potassium hydroxide → potassium cyanate (590-28-3) + potassium cyanide (151-50-8) + potassium carbonate

Conditions	Yield
im bedeckten Tiegel;

uric Acid (69-93-2) + potassium hydroxide → ammonia (7664-41-7) + potassium cyanide (151-50-8) + potassium oxalate (583-52-8) + potassium carbonate

methyl thiocyanate (556-64-9) + alcoholic KOH-solution → Dimethyldisulphide (624-92-0) + ammonia (7664-41-7) + potassium cyanide (151-50-8) + potassium carbonate

dipicryl-diazene (19159-68-3) + diluted KOH-solution → potassium cyanide (151-50-8) + 2,4,6-Trinitrophenol (88-89-1) + 2,2',4,4',6,6'-hexanitrohydrazobenzene (68683-32-9) + potassium nitrite

diethyl ether (60-29-7) + cyanogen iodide (506-78-5) + KOH → potassium cyanide (151-50-8)

bromocyane (506-68-3) + ethanol (64-17-5) + KOH → potassium cyanide (151-50-8)

cyanogen iodide (506-78-5) + ethanol (64-17-5) + KOH → potassium cyanide (151-50-8)

diethyl ether (60-29-7) + bromocyane (506-68-3) + chloroform (67-66-3) + KOH → potassium cyanide (151-50-8)

cyanogen iodide (506-78-5) + chloroform (67-66-3) + KOH → potassium cyanide (151-50-8)

bromocyane (506-68-3) + water (7732-18-5) + KOH → potassium cyanide (151-50-8)

cyanogen iodide (506-78-5) + water (7732-18-5) + KOH → potassium cyanide (151-50-8)

ethanedinitrile (460-19-5) + potassium → potassium cyanide (151-50-8)

ethanedinitrile (460-19-5) + potassium carbonate → potassium cyanate (590-28-3) + potassium cyanide (151-50-8)

Conditions	Yield
in der Rotglut;

ethyl isothiocyanate (542-90-5) + aqueous KOH-solution → Diethyl disulfide (110-81-6) + potassium cyanate (590-28-3) + potassium cyanide (151-50-8)

Conditions	Yield
at 100℃; im zugeschmolzenen Rohr;

trichloroacetonitrile (14752-58-0) + concentrated KOH-solution → ammonia (7664-41-7) + potassium cyanide (151-50-8)

Cyan-imidoameisensaeureethylester (13369-04-5) + alcoholic potash → potassium cyanide (151-50-8) + potassium fulminate

ethanedinitrile (460-19-5) + aqueous KOH-solution → potassium cyanide (151-50-8) + potassium fulminate

ethyl isocyanide (624-79-3) + potassium amide → potassium cyanide (151-50-8) + ethylamine (75-04-7)

ethyl isocyanide (624-79-3) + potassium amide + liquid.ammonia → potassium cyanide (151-50-8) + ethylamine (75-04-7)

Conditions	Yield
at 80℃;

ethanedinitrile (460-19-5) + aqueous KOH-solution → potassium cyanate (590-28-3) + ammonia (7664-41-7) + potassium cyanide (151-50-8) + azulminic acid

Conditions	Yield
Produkt5: CO2;

ethanedinitrile (460-19-5) + K2CO3 → potassium cyanate (590-28-3) + carbon dioxide (124-38-9) + potassium cyanide (151-50-8) + paracyan

Conditions	Yield
at 190 - 370℃; Produkt 5: Stickstoff;

1-bromo-octane (111-83-1) + potassium cyanide (151-50-8) → nonanonitrile (2243-27-8)

Conditions	Yield
Sucrose-ethyleneoxide adducts In acetonitrile at 83℃; for 24h; Product distribution; further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis; further solvents: toluene/H2O;	100%
tetraoctyl ammonium bromide In water; toluene at 90℃; for 24h; Product distribution; other phase-transfer catalysts, time;	99%
tetraoctyl ammonium bromide In water; toluene at 90℃; for 24h;	99%

potassium cyanide (151-50-8) + acetophenone (98-86-2) → 2-hydroxy-2-phenylpropionitrile (20102-12-9)

Conditions	Yield
Stage #1: potassium cyanide; acetophenone With 18-crown-6 ether In dichloromethane at 20℃; for 4h; Stage #2: With hydrogenchloride In tetrahydrofuran; dichloromethane at 0 - 20℃; for 2h;	100%
Stage #1: potassium cyanide; acetophenone With tetrachlorosilane In acetonitrile at 60 - 70℃; for 5h; Stage #2: With sodium hydrogencarbonate In water; acetonitrile Further stages.;	82%
With hydrogenchloride

potassium cyanide (151-50-8) + 1-bromomethyl-3-trifluoromethylbenzene (402-23-3) → 3-trifluoromethylphenylacetonitrile (2338-76-3)

Conditions	Yield
In ethanol; water for 1.5h; Heating / reflux;	100%
In dimethyl sulfoxide

3-pyridinecarboxaldehyde (500-22-1) + potassium cyanide (151-50-8) → 2-hydroxy-2-(pyridin-3-yl)acetonitrile (17604-74-9)

Conditions	Yield
With water; acetic acid at 5 - 10℃; for 2h;	100%
With hydrogenchloride
With acetic acid In water for 18h; Ambient temperature;

chloro-trimethyl-silane (75-77-4) + 6-methoxy-2-acetylnaphthalene (3900-45-6) + potassium cyanide (151-50-8) → 2-(6-methoxy-2-naphthyl)-2-(trimethylsilyloxy)propiononitrile (107727-73-1)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 13.5h;	100%

(+)-<(1S,2S)-1-Hydroxy-2-methyl-3-oxo-cyclopent-2-yl>-essigsaeure-γ-lacton (71629-66-8) + potassium cyanide (151-50-8) → (1S,2S)-6-Cyano-6-hydroxy-5-methyl-2-oxa-bicyclo<3.3.0>octan-3-on (98926-41-1)

Conditions	Yield
In water; acetic acid at 5℃; for 20h;	100%

Octanal (124-13-0) + methylamine hydrochloride (593-51-1) + potassium cyanide (151-50-8) → 2-Methylamino-nonanenitrile (112101-12-9)

Conditions	Yield
With aluminum oxide In acetonitrile at 50℃; for 22h; ultrasound;	100%

5-anti-Chloro-6-syn-cyanobicyclo<2.1.1>hexene (51991-03-8) + potassium cyanide (151-50-8) → endo,endo-3,5-Dicyanotricyclo<2.2.0.02.6>hexane (72431-16-4)

Conditions	Yield
In water; acetonitrile for 30h; Ambient temperature;	100%

9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizin-2-one (841-95-2) + potassium cyanide (151-50-8) → 2-Amino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-2-carbonitrile (133308-74-4)

Conditions	Yield
With ammonia; acetic acid In water at 40℃; for 25h; Irradiation; irrad. with ultrasound;	100%

potassium cyanide (151-50-8) + 1-Chloromethyl-7-methoxy-1,4,4-trimethyl-isothiochroman → 7-methoxy-1,4,4-trimethylisothiochroman-1-ylacetonitril (128276-86-8)

Conditions	Yield
In ethanol; water for 3h; Heating;	100%

potassium cyanide (151-50-8) + benzyl bromide (100-39-0) → phenylacetonitrile (140-29-4)

Conditions	Yield
Sucrose-ethyleneoxide adducts In acetonitrile at 20℃; for 8h; Product distribution; further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis; further solvents: toluene/H2O;	100%
With water; Aliquat 336 for 2h; Ambient temperature;	97%
With poly(ethylene glycol)-supported tetrabutylamminium bromide In water at 25℃; for 2h; Substitution;	97%

potassium cyanide (151-50-8) + aniline hydrochloride (142-04-1) + 4-fluorobenzaldehyde (459-57-4) → 2-(4-fluorophenyl)-2-(phenylamino) acetonitrile (124573-71-3)

Conditions	Yield
In ethanol; water 1.) 1 h cooling; 2.) 20 h room temperature;	100%

potassium cyanide (151-50-8) + <5-(Diphenylmethylen)-1,3-cyclopentadien-1-yl>dimethylsulfonium-perchlorat → 1-(Cyandiphenylmethyl)-2-(dimethylsulfonio)cyclopentadienid

Conditions	Yield
In methanol at 0℃; for 0.25h;	100%

potassium cyanide (151-50-8) + <5-(Diphenylmethylen)-1,3-cyclopentadien-1-yl>diphenylsulfonium-perchlorat → 1-(Cyandiphenylmethyl)-2-(diphenylsulfonio)cyclopentadienid

Conditions	Yield
In methanol at 0℃; for 0.25h;	100%

potassium cyanide (151-50-8) + <5-(Diphenylmethylen)-1,3-cyclopentadien-1-yl>bis(4-methylphenyl)sulfonium-perchlorat → 1--2-(cyandiphenylmethyl)cyclopentadienid

Conditions	Yield
In methanol at 0℃; for 0.25h;	100%

potassium cyanide (151-50-8) + ethyl [L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-pentenoate (104700-37-0) → (S)-4-tert-Butoxycarbonylamino-3-cyano-pentanoic acid ethyl ester

Conditions	Yield
With 18-crown-6 ether In acetonitrile for 24h; Ambient temperature;	100%

potassium cyanide (151-50-8) + 2-Benzyl-3-(bromomethyl)-1,4-dimethoxynaphthalene (161363-80-0) → 2-Benzyl-3-(cyanomethyl)-1,4-dimethoxynaphthalene (161363-81-1)

Conditions	Yield
In 1,4-dioxane; water for 10h; Heating;	100%

potassium cyanide (151-50-8) + trans-1-iodo-2-isothiocyanatocyclohexane (60211-89-4, 63616-13-7, 93424-19-2) → 2-cyano-cis-3a,4,5,6,7,7a-hexahydrobenzothiazole (77469-22-8)

Conditions	Yield
With 18-crown-6 ether In chloroform; water for 92h; Heating;	100%

potassium cyanide (151-50-8) + 4'-(chloromethyl)dispirobis<1,3>dioxole-6',1''-cyclohexane> (114200-84-9) → dispirobis<1,3>dioxole-6',1''-cyclohexane>-4'-acetonitrile (114200-85-0)

Conditions	Yield
With 18-crown-6 ether In acetonitrile for 5h; Heating;	100%

potassium cyanide (151-50-8) + diethyl <<3-(bromomethyl)phenyl>methyl>phosphonate (120667-42-7) → diethyl <<3-(cyanomethyl)phenyl>methyl>phosphonate (140151-14-0)

Conditions	Yield
With sodium iodide In water; acetone at 50℃; for 48h;	100%

potassium cyanide (151-50-8) + 4-(diethoxyphosphorylmethyl)-1-bromomethyl-phenyl (108228-81-5) → diethyl <<4-(cyanomethyl)phenyl>methyl>phosphonate (135335-15-8)

Conditions	Yield
With sodium iodide In water; acetone at 50℃; for 48h;	100%

potassium cyanide (151-50-8) + 3-(2,6-Dimethylphenyl)-4-methyl-5-acetyl-2-imino-thiazolin Hydrobromid → 2-Aminocarbonylimino-3-(2,6-dimethylphenyl)-4-methyl-5-acetyl-thiazolin

Conditions	Yield
In water	100%

potassium cyanide (151-50-8) + <5-(Diphenylmethylen)-1,3-cyclopentadien-1-yl>methylphenylsulfonium-perchlorat → 1-(Cyandiphenylmethyl)-2-(methylphenylsulfonio)cyclopentadienid

Conditions	Yield
In methanol at 0℃; for 0.25h;	100%

potassium cyanide (151-50-8) + ethyl 8,9-bis(4-methoxyphenyl)-10,10-dimethyl-5-oxotricyclo<5.2.1.02,6>deca-3,8-diene-2-carboxylate → (3aS,4R,7S,7aR)-3-Cyano-5,6-bis-(4-methoxy-phenyl)-8,8-dimethyl-1-oxo-1,2,3,4,7,7a-hexahydro-4,7-methano-indene-3a-carboxylic acid ethyl ester

Conditions	Yield
With ammonium chloride In water; N,N-dimethyl-formamide at 100℃; for 4.5h;	100%

potassium cyanide (151-50-8) + acetaldehyde (75-07-0) + 2-amino-1-phenylpropane (60-15-1, 156-34-3, 51-64-9, 300-62-9) → 2-<(1-methyl-2-phenylethyl)amino>propanenitrile (3535-04-4)

Conditions	Yield
With sodium hydrogensulfite In methanol; water Ambient temperature;	100%

methylamine hydrochloride (593-51-1) + potassium cyanide (151-50-8) + acetophenone (98-86-2) → 2-methylamino-2-phenyl-propionitrile (112101-15-2)

Conditions	Yield
With aluminum oxide In acetonitrile at 50℃; for 24h; ultrasound;	100%

potassium cyanide (151-50-8) + 3-methoxy-benzaldehyde (591-31-1) → m-methoxymandelonitrile (53313-94-3)

Conditions	Yield
Stage #1: 3-methoxy-benzaldehyde With hydrogenchloride; sodium sulfite In tetrahydrofuran; water at 20℃; for 0.166667h; Stage #2: potassium cyanide In tetrahydrofuran; water for 0.5h;	100%
With sodium hydrogensulfite 1) H2O, 40 deg C, 0.5 h, 2) H2O, 0 deg C, 1 h; Multistep reaction;
With acetic acid In water
With hydrogenchloride; sodium sulfite In tetrahydrofuran at 20℃; for 0.5h;

formaldehyd (50-00-0) + potassium cyanide (151-50-8) + benzyl-methyl-amine (103-67-3) → (N-benzyl-N-methylamino)acetonitrile (14321-25-6)

Conditions	Yield
With hydrogenchloride for 16h; Ambient temperature;	100%

potassium cyanide (151-50-8) + (1S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-7-hydroxy-4-oxo-2,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid → (1S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4-cyano-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4,7-dihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-5-carboxylic acid

Conditions	Yield
With acetic acid In methanol; isopropyl alcohol	100%

(2Z)-3-methyl-2-penten-4-ynal (52421-93-9) + potassium cyanide (151-50-8) → (Z)-1-cyano-3-methylpent-2-en-4-yn-1-ol

Conditions	Yield
With hydrogenchloride In diethyl ether; water 30 min, 0 deg C; 2 h, 20 deg C;	100%

Upstream product

• 590-28-3 potassium cyanate 
• 14219-01-3 potassium acetamide 
• 86712-42-7 2,3-dianilino-2,3-diphenyl-propionitrile 
• 333-20-0 potassium thioacyanate 
• 14271-73-9 4-methylbenzoyl cyanide 
• 40626-45-7 α,α-dichlorobenzylcyanide 
• 505-14-6 thiocyanogen 
• 506-78-5 cyanogen iodide 
• 460-19-5 ethanedinitrile 
• 7664-41-7 ammonia 
• 542-90-5 ethyl isothiocyanate 
• 624-79-3 ethyl isocyanide 
• 13369-04-5 Cyan-imidoameisensaeureethylester 
• 14752-58-0 trichloroacetonitrile 

Downstream Products

• 10386-27-3 2-bromoisonicotinonitrile 
• 107920-46-7 benzoyloxy-(5,6-dihydro-2H-pyran-3-yl)-acetonitrile 
• 53425-61-9 1-benzoyl-6-methyl-1,2-dihydro-quinoline-2-carbonitrile 
• 21259-77-8 2-benzoyl-3-methyl-1,2-dihydroisoquinoline-1-carbonitrile 
• 29030-58-8 (4-cyclohexyl-phenyl)-acetonitrile 
• 69873-74-1 (Z)-N-(m-tolyl)benzimidoyl cyanide 
• 123241-32-7 2-ethoxy-6-nitro-benzonitrile 
• 3646-57-9 bis(4-nitrophenyl)diazene 
• 100-29-8 1-ethoxy-4-nitrobenzene 
• 101-63-3 bis(4-nitrophenyl)ether 
• 66293-57-0 1-benzoyl-7-chloro-1,2-dihydro-quinoline-2-carbonitrile 
• 75434-14-9 1-benzoyl-6-chloro-1,2-dihydro-quinoline-2-carbonitrile 
• 855196-53-1 2-(pyridin-3-yl)benzonitrile 
• 443-75-4 2-(6-fluoro-1H-indol-3-yl)acetic acid 

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Synthesis of an α-amino nitrile and a bis α-amino nitrile derivative of thiadiazole: Reaction mechanism

The first nucleophilic addition of an inorganic nucleophile (cyanide) to the activated, rigid, α-diazomethine groups of a 1,2,5-thiadiazole 1,1-dioxide is reported here. An α-amino nitrile and a bis a-amino nitrile derivatives were obtained in good yields (62 and 98%, respectively) and characterized by spectroscopic, analytical, and single crystal X-ray diffraction techniques. The course of the reaction, followed by cyclic voltammetry (CV), showed that cyanide adds to only one of the two C=N double bonds of the thiadiazole, forming an anion from which an N-methyl derivative was obtained. Adequate concentrations of cyanide and methyl iodide (MeI) produced directly the bis a-amino nitrile derivative. Copyright