Product Name

  • Name

    Cyanide

  • EINECS
  • CAS No. 57-12-5
  • Article Data187
  • CAS DataBase
  • Density 0.695g/cm3
  • Solubility Miscible with water.
  • Melting Point 148 °C (decomp)
  • Formula CN
  • Boiling Point 25.7°Cat760mmHg
  • Molecular Weight 26.0177
  • Flash Point °C
  • Transport Information
  • Appearance
  • Safety Very poisonous by most routes. Cyanide directly stimulates the chemoreceptors of the carotid and aortic bodies with a resultant hyperpnea (increase in the depth and rate of respiration). Cardiac irregularities are often noted, but the heart invariably outlasts the respirations. Death is due to respiratory arrest of central origin. It can occur within seconds or minutes of the inhalation of high concentrations of HCN gas. Because of slower absorption, death may be more delayed after the ingestion of cyanide salts, but the critical events still occur within the first hour. Two other sources of cyanide have been responsible for human poisoning: the naturally occurring amygdalin and the drug nitroprusside.

    Amygdalin is a cyanogenic glycoside found in apricot, peach, and similar fruit pits and in sweet almonds (Sayre and Kaymakcalan, 1941). It is a chemical combination of glucose, benzaldehyde, and cyanide from which the latter can be released by the action of β-glucosidase or emulsion. Although these enzymes are not found in mammalian tissues, the human intestinal microflora appears to possess these or similar enzymes capable of effecting cyanide release resulting in human poisoning. For this reason, amygdalin may be as much as 40 times more toxic by the oral route as compared with intravenous injection. Amygdalin is the major ingredient of Laetrile, and this alleged anticancer drug has also been responsible for human cyanide poisoning.

    An ethical drug that may also cause cyanide poisoning in overdose is the potent vascular smooth-muscle relaxant sodium nitroprusside. Although nitroprusside is related chemically to ferricyanide, unlike the latter it penetrates into erythrocytes and reacts with hemoglobin to release its cyanide (Smith and Kruszyna, 1974). Fortunately, the therapeutic margin for nitroprusside appears to be quite large.

    Cyanide is commonly found in certain rat and pest poisons, silver and metal polishes, photographic solutions, and fumigating products. Compounds such as potassium cyanide can also be readily purchased from chemical stores. Cyanide is readily absorbed from all routes, including the skin, mucous membranes, and by inhalation, although alkali salts of cyanide are toxic only when ingested. Death may occur with ingestion of even small amounts of sodium or potassium cyanide and can occur within minutes or hours depending on route of exposure. Inhalation of toxic fumes represents a potentially rapidly fatal type of exposure. A blood cyanide level of greater than 0.2 µg/mL is considered toxic. Lethal cases have usually had levels above 1 µg/mL.

    Clinically, cyanide poisoning is reported to produce a bitter, almond odor on the breath of the patient; however, only a small proportion of the population is genetically able to discern this characteristic odor. Typically, cyanide has a bitter, burning taste, and, following poisoning, symptoms of salivation, nausea without vomiting, anxiety, confusion, vertigo, giddiness, lower-jaw stiffness, convulsions, opisthotonos, paralysis, coma, cardiac arrhythmias, and transient respiratory stimulation followed by respiratory failure may occur. Bradycardia is a common finding, but in most cases heartbeat usually outlasts respiration (Wexler et al., 1947). A prolonged expiratory phase is considered to be characteristic of cyanide poisoning. (Casarett and Doull's, Toxicology, The Basic Science of Poisons 2nd ed. Doull, Klaassen and Amdur (eds), Macmillan Pub. Co. Inc. New York, NY).

    The volatile cyanides resemble HCN physiologically, inhibiting tissue oxidation and causing death through asphyxia. Cyanogen is probably as toxic as HCN; the nitriles are generally considered somewhat less toxic, probably because of their lower volatility. The non-volatile cyanide salts appear to be relatively nontoxic systemically, so long as they are not ingested and care is taken to prevent the formation of HCN. Workers, such as electroplaters and picklers, who are daily exposed to cyanide solutions may develop a “cyanide” rash, characterized by itching, and by macular, papular, and vesicular eruptions. Frequently there is secondary infection. Exposure to small amounts of cyanide compounds over long periods of time is reported to cause loss of appetite, headache, weakness, nausea, dizziness, and symptoms of irritation of the upper respiratory tract and eyes. See also specific cyanide compounds.

    Flammable by chemical reaction with heat, moisture, acid. Many cyanides rather easily evolve HCN, a flammable gas that is highly toxic. Carbon dioxide from the air is sufficiently acidic to liberate HCN from cyanide solutions. Reaction with hypochlorite solutions may be violent at pH 10.0–10.3. Cyanides explode if melted with nitrites or chlorates at about 450°. Violent reaction with F2, Mg, nitrates, HNO3, nitrites. Metal cyanides are easily oxidized and may be thermally unstable. N-cyano derivatives may be reactive or unstable. Many organic nitriles can be very reactive under the right conditions. When heated to decomposition or on contact with acid, acid fumes, water, or steam, cyanides emit toxic and flammable vapors of CN. See also HYDROCYANIC ACID.

    Analytical Methods:

       

    For occupational chemical analysis use OSHA: #ID-120 or NIOSH: Cyanides (Aerosol and Gas) 7904.

  • Risk Codes
  • Molecular Structure Molecular Structure of 57-12-5 (Cyanide)
  • Hazard Symbols
  • Synonyms Carbonnitride ion (CN1-); Cyanide (CN1-); Cyanide anion; Cyanide ion; Cyanide ion(CN(1-)); Cyanide ion(1-); Cyanide(1-); Cyanide(1-) ion; Hydrocyanic acid, ion(1-);Isocyanide; Nitrile anion
  • PSA 23.79000
  • LogP 0.09638

Synthetic route

N-chloro-succinimide
128-09-6

N-chloro-succinimide

mercury(II) diacetate
1600-27-7

mercury(II) diacetate

potassium thioacyanate
333-20-0

potassium thioacyanate

A

Succinimide
123-56-8

Succinimide

B

cyanide(1-)
57-12-5

cyanide(1-)

C

chloride
16887-00-6

chloride

D

Sulfate
14808-79-8

Sulfate

E

hydrogen cation

hydrogen cation

Conditions
ConditionsYield
With perchloric acid In methanol; water Kinetics; oxidation of SCN(1-) by NCS in aq. methanol in presence of mercuric acetate and HClO4 (room temp.); gravimetric and iodometric methods;A n/a
B n/a
C n/a
D 94%
E n/a
With sodium hydroxide In methanol; water Kinetics; oxidation of SCN(1-) by NCS in aq. methanol in presence of mercuric acetate and NaOH at 303 K; gravimetric and iodometric methods;A n/a
B n/a
C n/a
D 94%
E n/a
hydrogen cyanide
74-90-8

hydrogen cyanide

cyanide(1-)
57-12-5

cyanide(1-)

Conditions
ConditionsYield
With D2O*DO- at 24.9℃; Rate constant; amount of added solvent vapor dependence;
With CH3OH*CH3O- at 24.9℃; Rate constant; amount of added solvent vapor dependence;
methyl isocyanate
593-75-9, 685498-28-6

methyl isocyanate

methanolate
3315-60-4

methanolate

A

cyanide(1-)
57-12-5

cyanide(1-)

B

isocyanomethide anion
81704-80-5

isocyanomethide anion

C

acetone
67-64-1

acetone

Conditions
ConditionsYield
at 24.9℃; under 0.4 Torr; Product distribution; Thermodynamic data; reaction enthalpy;
methyl isocyanate
593-75-9, 685498-28-6

methyl isocyanate

A

methanol
67-56-1

methanol

B

cyanide(1-)
57-12-5

cyanide(1-)

C

isocyanomethide anion
81704-80-5

isocyanomethide anion

Conditions
ConditionsYield
With hydroxide at 24.9℃; under 0.4 Torr; Product distribution; Thermodynamic data; reaction enthalpy;
methyl isocyanate
593-75-9, 685498-28-6

methyl isocyanate

A

Methyl fluoride
593-53-3

Methyl fluoride

B

cyanide(1-)
57-12-5

cyanide(1-)

Conditions
ConditionsYield
With fluoride at 24.9℃; under 0.4 Torr; Product distribution; Thermodynamic data; Rate constant; reaction enthalpy;
thiophenolate
13133-62-5

thiophenolate

sodium ethanolate
141-52-6

sodium ethanolate

(2-Isocyano-ethanesulfonyl)-benzene

(2-Isocyano-ethanesulfonyl)-benzene

A

cyanide(1-)
57-12-5

cyanide(1-)

B

PVS
5535-48-8

PVS

C

2-ethoxyethyl phenyl sulphone
28525-26-0

2-ethoxyethyl phenyl sulphone

D

(2-Isocyano-ethylsulfanyl)-benzene
3126-28-1

(2-Isocyano-ethylsulfanyl)-benzene

Conditions
ConditionsYield
Rate constant; Product distribution; multistep reaction, 1.) ethanol, 25 deg C; 2.) ethanol;
thiophenolate
13133-62-5

thiophenolate

(2-Isocyano-ethoxy)-benzene

(2-Isocyano-ethoxy)-benzene

A

cyanide(1-)
57-12-5

cyanide(1-)

B

vinyl phenyl ether
766-94-9

vinyl phenyl ether

C

phenolate
3229-70-7

phenolate

D

(2-Isocyano-ethylsulfanyl)-benzene
3126-28-1

(2-Isocyano-ethylsulfanyl)-benzene

Conditions
ConditionsYield
With sodium ethanolate Rate constant; Product distribution; multistep reaction, 1.) ethanol, 25 deg C; 2.) ethanol;
Pyronin G nitrile
77372-52-2

Pyronin G nitrile

A

cyanide(1-)
57-12-5

cyanide(1-)

B

pyronin*BF4-
85338-00-7

pyronin*BF4-

Conditions
ConditionsYield
With tetrafluoroborate ion In water; acetonitrile at 23℃; Equilibrium constant;
3,6-Bis-dimethylamino-9H-thioxanthene-9-carbonitrile
128228-27-3

3,6-Bis-dimethylamino-9H-thioxanthene-9-carbonitrile

A

cyanide(1-)
57-12-5

cyanide(1-)

B

thiopyronin fluoroborate

thiopyronin fluoroborate

Conditions
ConditionsYield
With tetrafluoroborate ion In water; acetonitrile at 23℃; Equilibrium constant;
potassium cyanide
151-50-8

potassium cyanide

(2-Isocyano-ethylsulfanyl)-benzene
3126-28-1

(2-Isocyano-ethylsulfanyl)-benzene

A

thiophenolate
13133-62-5

thiophenolate

B

cyanide(1-)
57-12-5

cyanide(1-)

C

β-cyanoethylisocyanide

β-cyanoethylisocyanide

D

phenylthioethylene
1822-73-7

phenylthioethylene

Conditions
ConditionsYield
With sodium ethanolate Rate constant; Product distribution; multistep reaction, 1.) ethanol, 25 deg C; 2.) ethanol;
C17H8N3(1-)

C17H8N3(1-)

A

cyanide(1-)
57-12-5

cyanide(1-)

B

2-fluoren-9-ylidene-malononitrile
1989-32-8

2-fluoren-9-ylidene-malononitrile

Conditions
ConditionsYield
In sulfolane; water at 25℃; Rate constant;
isocyanomethide anion
81704-80-5

isocyanomethide anion

A

cyanide(1-)
57-12-5

cyanide(1-)

B

cyanate
71000-82-3

cyanate

Conditions
ConditionsYield
With oxygen at 24.9℃; under 0.4 Torr; Product distribution; various neutral molecules with or without acidic hydrogen;
cyclopentadienylidene anion radical
4729-01-5

cyclopentadienylidene anion radical

acrylonitrile
107-13-1

acrylonitrile

A

1-cyano-vinyl
15091-87-9

1-cyano-vinyl

B

1-cyano-ethenide
36259-97-9

1-cyano-ethenide

C

cyanide(1-)
57-12-5

cyanide(1-)

D

cyclopenta-2,4-dienyl
2143-53-5

cyclopenta-2,4-dienyl

E

cyclopentadienide
20171-65-7

cyclopentadienide

F

C8H6N(1-)

C8H6N(1-)

Conditions
ConditionsYield
at 24.9℃; under 0.5 Torr; Rate constant; Mechanism; Product distribution; different α,β-unsaturated molecules;
methylenecyclopropene anion

methylenecyclopropene anion

A

cyanide(1-)
57-12-5

cyanide(1-)

B

2-nitrosoallyl anion

2-nitrosoallyl anion

Conditions
ConditionsYield
With dinitrogen monoxide In gas under 0.4 Torr;
methyl cyanoformate
17640-15-2

methyl cyanoformate

methanolate
3315-60-4

methanolate

A

cyanide(1-)
57-12-5

cyanide(1-)

B

Nitrilo-acetic acid anion
109909-16-2

Nitrilo-acetic acid anion

Conditions
ConditionsYield
for 0.000416667h; Mechanism;
methyl cyanoformate
17640-15-2

methyl cyanoformate

phenylmethanide
18860-15-6

phenylmethanide

A

cyanide(1-)
57-12-5

cyanide(1-)

B

Nitrilo-acetic acid anion
109909-16-2

Nitrilo-acetic acid anion

C

benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

Conditions
ConditionsYield
for 0.000416667h; Mechanism;
4-cyano-1-(2,6-dichloro-benzyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diamide
106473-05-6

4-cyano-1-(2,6-dichloro-benzyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid diamide

water
7732-18-5

water

A

cyanide(1-)
57-12-5

cyanide(1-)

B

3,5-dicarbamoyl-1-(2,6-dichloro-benzyl)-pyridinium

3,5-dicarbamoyl-1-(2,6-dichloro-benzyl)-pyridinium

Conditions
ConditionsYield
at 20℃; Equilibrium constant;
methyl isocyanate
624-83-9

methyl isocyanate

A

methyl hydroperoxide
3031-73-0

methyl hydroperoxide

B

cyanide(1-)
57-12-5

cyanide(1-)

C

cyanate
71000-82-3

cyanate

D

C2H3NO2(1-)

C2H3NO2(1-)

E

HO

HO

Conditions
ConditionsYield
With hydroperoxide anion In gaseous matrix at 26.9℃; Rate constant; Product distribution; in a flowing afterglow system (flow rector affixed to a quadrupole mass spectrometer);
dithiooxamide
79-40-3

dithiooxamide

concentrated KOH-solution

concentrated KOH-solution

A

cyanide(1-)
57-12-5

cyanide(1-)

B

Thiocyanate
302-04-5

Thiocyanate

C

sulfide

sulfide

thiocyanic acid
463-56-9

thiocyanic acid

copper

copper

cyanide(1-)
57-12-5

cyanide(1-)

thiocyanic acid
463-56-9

thiocyanic acid

iron turnings

iron turnings

cyanide(1-)
57-12-5

cyanide(1-)

thiocyanic acid
463-56-9

thiocyanic acid

iron-zinc-alloy

iron-zinc-alloy

cyanide(1-)
57-12-5

cyanide(1-)

thiocyanic acid
463-56-9

thiocyanic acid

water
7732-18-5

water

iron

iron

ferrous chloride

ferrous chloride

cyanide(1-)
57-12-5

cyanide(1-)

Conditions
ConditionsYield
at 140 - 150℃;
thiocyanic acid
463-56-9

thiocyanic acid

water
7732-18-5

water

iron

iron

iron monoxide hydrate

iron monoxide hydrate

cyanide(1-)
57-12-5

cyanide(1-)

Conditions
ConditionsYield
at 110 - 120℃;
at 110 - 120℃;
thiocyanic acid
463-56-9

thiocyanic acid

lead

lead

cyanide(1-)
57-12-5

cyanide(1-)

thiocyanic acid
463-56-9

thiocyanic acid

iron

iron

lead

lead

cyanide(1-)
57-12-5

cyanide(1-)

thiocyanic acid
463-56-9

thiocyanic acid

lime/chalk/

lime/chalk/

coal

coal

cyanide(1-)
57-12-5

cyanide(1-)

thiocyanic acid
463-56-9

thiocyanic acid

lime/chalk/

lime/chalk/

coal

coal

iron

iron

cyanide(1-)
57-12-5

cyanide(1-)

thiocyanic acid
463-56-9

thiocyanic acid

iron turnings

iron turnings

pitch

pitch

cyanide(1-)
57-12-5

cyanide(1-)

thiocyanic acid
463-56-9

thiocyanic acid

potash

potash

coal

coal

iron

iron

oil

oil

cyanide(1-)
57-12-5

cyanide(1-)

cyanide(1-)
57-12-5

cyanide(1-)

cyanate
71000-82-3

cyanate

Conditions
ConditionsYield
With 4,40-Di-tert-butyl-2,20-bipyridine; dihydrogen peroxide In N,N-dimethyl-formamide at 20℃; for 2.5h; Catalytic behavior; Kinetics; Reagent/catalyst;100%
With alkali peroxide In not given in alkaline soln.;;
With chlorine In water byproducts: Cl(1-); introduction of Cl2 into alkali cyanide soln.;
cyanide(1-)
57-12-5

cyanide(1-)

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In tetrachloromethane with alkali cyanides, under 3°C;98%
With chlorine In neat (no solvent) alkali cyanides, at -18°C;85%
With chlorine In neat (no solvent) alkali cyanides mixed with sand at 3°C;80%
With chlorine In tetrachloromethane alkali cyanides, at 0°C;
With hydrogenchloride In not given
cyanide(1-)
57-12-5

cyanide(1-)

[(η6-p-(i-Pr)C6H4Me)RuCl(κ2-2,2'-dipyridylamine)]BF4
1248572-08-8

[(η6-p-(i-Pr)C6H4Me)RuCl(κ2-2,2'-dipyridylamine)]BF4

[(η6-p-(i-Pr)C6H4Me)Ru(κ2-2,2'-dipyridylamine)(CN)]BF4
1248572-18-0

[(η6-p-(i-Pr)C6H4Me)Ru(κ2-2,2'-dipyridylamine)(CN)]BF4

Conditions
ConditionsYield
In methanol CN(1-) was added to suspn. of Ru complex in MeOH; refluxed for 4 h; evapd. (vac.); dissolved in CH2Cl2; filtered; concd.; hexane added; septd.; washed (Et2O); dried (vac.); elem. anal.;98%
cyanide(1-)
57-12-5

cyanide(1-)

[(η6-p-iPrC6H4Me)RuCl(κ2-dpb)]BF4

[(η6-p-iPrC6H4Me)RuCl(κ2-dpb)]BF4

[(η6-p-(i-Pr)C6H4Me)Ru(κ2-di-2-pyridylbenzylamine)(CN)]BF4
1248572-24-8

[(η6-p-(i-Pr)C6H4Me)Ru(κ2-di-2-pyridylbenzylamine)(CN)]BF4

Conditions
ConditionsYield
In methanol CN(1-) was added to suspn. of Ru complex in MeOH; refluxed for 4 h; evapd. (vac.); dissolved in CH2Cl2; filtered; concd.; hexane added; septd.; washed (Et2O); dried (vac.); elem. anal.;97%
((HB(C3H3N2)3)W(P(CH3)3)(NO)(C6H5(OCH3)C2H4COH))(1+)*CF3SO3(1-)=((HB(C3H3N2)3)W(P(CH3)3)(NO)(C6H5(OCH3)C2H4COH))CF3SO3

((HB(C3H3N2)3)W(P(CH3)3)(NO)(C6H5(OCH3)C2H4COH))(1+)*CF3SO3(1-)=((HB(C3H3N2)3)W(P(CH3)3)(NO)(C6H5(OCH3)C2H4COH))CF3SO3

cyanide(1-)
57-12-5

cyanide(1-)

diphenylammonium trifluoromethanesulfonate

diphenylammonium trifluoromethanesulfonate

[TpW(NO)(PMe3)(5,6-η2-7-methoxy-3,4,4a,8,8a-tetrahydro-2H-chromen-7-onium-2-carbonitrile)](OTf)

[TpW(NO)(PMe3)(5,6-η2-7-methoxy-3,4,4a,8,8a-tetrahydro-2H-chromen-7-onium-2-carbonitrile)](OTf)

Conditions
ConditionsYield
In not given DMF or MeOH;93%
[4,5-η2-[Os(NH3)5]-1-methylthiophenium](OTf)3

[4,5-η2-[Os(NH3)5]-1-methylthiophenium](OTf)3

cyanide(1-)
57-12-5

cyanide(1-)

[Os(NH3)5CNC4H4SCH3](2+)*2(CF3SO2O)(1-)=[Os(NH3)5CNC4H4SCH3](CF3SO3)2

[Os(NH3)5CNC4H4SCH3](2+)*2(CF3SO2O)(1-)=[Os(NH3)5CNC4H4SCH3](CF3SO3)2

Conditions
ConditionsYield
91%
cyanide(1-)
57-12-5

cyanide(1-)

A

hydrogen cyanide
74-90-8

hydrogen cyanide

B

cyanogen chloride
506-77-4

cyanogen chloride

Conditions
ConditionsYield
With chlorine In hydrogenchloride alkali cyanides, pH=9;A n/a
B 90%
cyanide(1-)
57-12-5

cyanide(1-)

para-bromophenacyl bromide
99-73-0

para-bromophenacyl bromide

3-(4-bromophenyl)-3-oxopropanenitrile
4592-94-3

3-(4-bromophenyl)-3-oxopropanenitrile

Conditions
ConditionsYield
With β-cyclodextrin-silica nanocomposite linked by propyl spacer In water at 90℃; for 1.25h; Green chemistry;90%
[4,5-η2-[Os(NH3)5]-1-methylbenzo[b]thiophenium](OTf)3

[4,5-η2-[Os(NH3)5]-1-methylbenzo[b]thiophenium](OTf)3

cyanide(1-)
57-12-5

cyanide(1-)

[Os(NH3)5(C4H4C4H2(CN)SCH3)](2+)*2(CF3SO2O)(1-)=[Os(NH3)5(C4H4C4H2(CN)SCH3)](CF3SO3)2

[Os(NH3)5(C4H4C4H2(CN)SCH3)](2+)*2(CF3SO2O)(1-)=[Os(NH3)5(C4H4C4H2(CN)SCH3)](CF3SO3)2

Conditions
ConditionsYield
89%
cyanide(1-)
57-12-5

cyanide(1-)

4-Nitrophenacyl bromide
99-81-0

4-Nitrophenacyl bromide

(4-Nitrobenzoyl)acetonitrile
3383-43-5

(4-Nitrobenzoyl)acetonitrile

Conditions
ConditionsYield
With β-cyclodextrin-silica nanocomposite linked by propyl spacer In water at 90℃; for 1h; Green chemistry;80%
(HB(C3H3N2)3)W(P(CH3)3)(NO)(C6H5(OCH3)C2H4COCH3)(1+)*CF3SO3(1-)=((HB(C3H3N2)3)W(P(CH3)3)(NO)(C6H5(OCH3)C2H4COCH3))CF3SO3

(HB(C3H3N2)3)W(P(CH3)3)(NO)(C6H5(OCH3)C2H4COCH3)(1+)*CF3SO3(1-)=((HB(C3H3N2)3)W(P(CH3)3)(NO)(C6H5(OCH3)C2H4COCH3))CF3SO3

cyanide(1-)
57-12-5

cyanide(1-)

diphenylammonium trifluoromethanesulfonate

diphenylammonium trifluoromethanesulfonate

[TpW(NO)(PMe3)(5,6-η2-7-methoxy-2-methyl-3,4,4a,8,8a-tetrahydro-2H-chromen-7-onium-2-carbonitrile)](OTf)

[TpW(NO)(PMe3)(5,6-η2-7-methoxy-2-methyl-3,4,4a,8,8a-tetrahydro-2H-chromen-7-onium-2-carbonitrile)](OTf)

Conditions
ConditionsYield
In not given DMF or MeOH;75%
{(CO)3Mo(μ-bis(diphenylphosphino)methane)2PtH(Cl)}*0.5(benzene)

{(CO)3Mo(μ-bis(diphenylphosphino)methane)2PtH(Cl)}*0.5(benzene)

cyanide(1-)
57-12-5

cyanide(1-)

{(CO)3Mo(μ-bis(diphenylphosphino)methane)2PtH(CN)}

{(CO)3Mo(μ-bis(diphenylphosphino)methane)2PtH(CN)}

Conditions
ConditionsYield
With NMe4(1+) In dichloromethane; water mixt. of Mo complex in CH2Cl2 and CN(1-) in water stirred in presence of NMe4(1+) as phase-transfer catalyst for 4 h; CH2Cl2 layer sepd., evapd. under vac., recrystd. from CH2Cl2-MeOH; elem. anal.;73%
2N(C2H5)4(1+)*{NiFe3S4(P(C6H5)3)(SC2H5)3}(2-)={N(C2H5)4}2{NiFe3S4(P(C6H5)3)(SC2H5)3}

2N(C2H5)4(1+)*{NiFe3S4(P(C6H5)3)(SC2H5)3}(2-)={N(C2H5)4}2{NiFe3S4(P(C6H5)3)(SC2H5)3}

cyanide(1-)
57-12-5

cyanide(1-)

A

(Et4N)3{Fe4S4(SEt)4}

(Et4N)3{Fe4S4(SEt)4}

B

{NiFe3S4(SC2H5)3CN}(3-)

{NiFe3S4(SC2H5)3CN}(3-)

Conditions
ConditionsYield
In acetonitrile byproducts: P(C6H5)3; under N2; monitored by (1)H-NMR;A 14%
B 70%
(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-5-((E)-2-nitrovinyl)tetrahydrofuro[2,3-d][1,3]dioxole
71485-92-2

(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-5-((E)-2-nitrovinyl)tetrahydrofuro[2,3-d][1,3]dioxole

cyanide(1-)
57-12-5

cyanide(1-)

5,6-Dideoxy-1,2-O-isopropylidene-3-O-methyl-5-C-methylene-α-D-xylo-hexofuranurononitrile
83905-33-3

5,6-Dideoxy-1,2-O-isopropylidene-3-O-methyl-5-C-methylene-α-D-xylo-hexofuranurononitrile

Conditions
ConditionsYield
68%
cyanide(1-)
57-12-5

cyanide(1-)

3-(4-chlorophenyl)-3H-tetrazolo[1,5-a]pyridin-4-ium tetrafluoroborate

3-(4-chlorophenyl)-3H-tetrazolo[1,5-a]pyridin-4-ium tetrafluoroborate

A

(2Z,4Z)-5-[2-(4-Chloro-phenyl)-2H-tetrazol-5-yl]-penta-2,4-dienenitrile
74795-88-3

(2Z,4Z)-5-[2-(4-Chloro-phenyl)-2H-tetrazol-5-yl]-penta-2,4-dienenitrile

B

(2E,4Z)-5-[2-(4-Chloro-phenyl)-2H-tetrazol-5-yl]-penta-2,4-dienenitrile
74795-79-2

(2E,4Z)-5-[2-(4-Chloro-phenyl)-2H-tetrazol-5-yl]-penta-2,4-dienenitrile

Conditions
ConditionsYield
In acetonitrileA 15%
B 67%
In acetonitrileA 67%
B 15%
(C4H6C6H5)Fe(CO)3(1+)*BF4(1-)={(C4H6C6H5)Fe(CO)3}BF4

(C4H6C6H5)Fe(CO)3(1+)*BF4(1-)={(C4H6C6H5)Fe(CO)3}BF4

cyanide(1-)
57-12-5

cyanide(1-)

(C10H11CN)Fe(CO)3
138368-23-7

(C10H11CN)Fe(CO)3

Conditions
ConditionsYield
In diethyl ether addn. of cyanide to suspn. of Fe-complex (molar ratio = 1 : 1, 15°C), stirring (15°C, 3 - 4 h); concentrating (reduced pressure), addn. of ice-cold H2O, extn. (ether), drying (Na2SO4), solvent removal, chromy. (SiO2, pentane), solvent removal, recrystn. (pentane); elem. anal.;54%
NbCl2(C6H4O2)(OC6H4OH)
105659-10-7

NbCl2(C6H4O2)(OC6H4OH)

cyanide(1-)
57-12-5

cyanide(1-)

(CN)2Nb(OC6H4O)(OC6H4OH)
110625-37-1

(CN)2Nb(OC6H4O)(OC6H4OH)

Conditions
ConditionsYield
In tetrahydrofuran NaCN or KCN was added to a THF soln. of Nb-compound in 2:1 ratio under anhyd. conditions, mixt. was stirred and refluxed for ca. 12 h at 65-70°C; filtered, ppt. was washed with THF, filtrate and washings were evapd. in vacuo (2 h), residue was recrystd. from EtOH, dried under vac. (0.4 mmHg); elem. anal.;45%
Nb(5+)*2Cl(1-)*C6H3O2(OH)(2-)*2H(1+)*C6H3O3(3-)=NbCl2(C6H3O2(OH))(OC6H3(OH)2)

Nb(5+)*2Cl(1-)*C6H3O2(OH)(2-)*2H(1+)*C6H3O3(3-)=NbCl2(C6H3O2(OH))(OC6H3(OH)2)

cyanide(1-)
57-12-5

cyanide(1-)

Nb(5+)*2CN(1-)*C6H3O2(OH)(2-)*2H(1+)*C6H3O3(3-)=Nb(CN)2(C6H3O2(OH))(OC6H3(OH)2)

Nb(5+)*2CN(1-)*C6H3O2(OH)(2-)*2H(1+)*C6H3O3(3-)=Nb(CN)2(C6H3O2(OH))(OC6H3(OH)2)

Conditions
ConditionsYield
In tetrahydrofuran NaCN or KCN was added to a THF soln. of Nb-compound in 2:1 ratio under anhyd. conditions, mixt. was stirred and refluxed for ca. 12 h at 65-70°C; filtered, ppt. was washed with THF, filtrate and washings were evapd. in vacuo (2 h), residue was recrystd. from EtOH, dried under vac. (0.4 mmHg); elem. anal.;45%
cyanide(1-)
57-12-5

cyanide(1-)

C30H30Br2N4(2-)*Ni(2+)

C30H30Br2N4(2-)*Ni(2+)

A

C31H31N5(2-)*Ni(2+)

C31H31N5(2-)*Ni(2+)

B

C32H30N6(2-)*Ni(2+)

C32H30N6(2-)*Ni(2+)

Conditions
ConditionsYield
In quinoline at 240℃;A 35%
B 32%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

cyanide(1-)
57-12-5

cyanide(1-)

cobalt(II) diacetate tetrahydrate
6147-53-1

cobalt(II) diacetate tetrahydrate

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

[CoCN(dimethylglyoximato)2(2,2'-bipyridine)]*1/3H2O

[CoCN(dimethylglyoximato)2(2,2'-bipyridine)]*1/3H2O

Conditions
ConditionsYield
With ogygen In ethanol; water under N2 atm. aq. soln. Co(OAc)2*4H2O and MCN (M = Na or K) was added toboiling soln. ligand in EtOH, refluxed for 2 h, cooled to room temp., b ipy was added, O2 was bubbled through react. mixt. for 3 h; ppt. was filtered, washed with 50 % aq. EtOH and EtOH and dried over CaCl2; elem. anal.;14.4%
ethylenediaminetetraacetatonickel(II)(2-)
748113-84-0, 14931-84-1

ethylenediaminetetraacetatonickel(II)(2-)

cyanide(1-)
57-12-5

cyanide(1-)

tetracyanonickelate(II)

tetracyanonickelate(II)

Conditions
ConditionsYield
1%
1%
With ethylenediaminetetraacetic acid Kinetics; slow react.;
With EDTA Kinetics; slow react.;
cyanide(1-)
57-12-5

cyanide(1-)

[Pt(CN(tert-butyl))2(7,8-benzoquinolate)](1+)
1130782-46-5

[Pt(CN(tert-butyl))2(7,8-benzoquinolate)](1+)

[Pt(benzoquinolate)(CN)(CN-tBu)]
1356474-74-2, 1356699-05-2

[Pt(benzoquinolate)(CN)(CN-tBu)]

[Pt(benzoquinolate)(CN)(CNtBu)]
1356474-74-2, 1356699-05-2

[Pt(benzoquinolate)(CN)(CNtBu)]

Conditions
ConditionsYield
A 1%
B n/a
cyanide(1-)
57-12-5

cyanide(1-)

[Pt(benzoquinolinate)(2,6-dimethylphenylisocyanide)2](1+)
1130782-48-7

[Pt(benzoquinolinate)(2,6-dimethylphenylisocyanide)2](1+)

[Pt(benzoquinolate)(CN)(CN-2,6-dimethylphenyl)]
1356474-80-0, 1356699-07-4

[Pt(benzoquinolate)(CN)(CN-2,6-dimethylphenyl)]

[Pt(benzoquinolate)(CN)(CN-2,6-dimethylphenyl)]
1356474-80-0, 1356699-07-4

[Pt(benzoquinolate)(CN)(CN-2,6-dimethylphenyl)]

Conditions
ConditionsYield
A 1%
B n/a
4-oxo-crotonic acid
1575-59-3

4-oxo-crotonic acid

cyanide(1-)
57-12-5

cyanide(1-)

succinic acid
110-15-6

succinic acid

Conditions
ConditionsYield
Mechanism;
cyanide(1-)
57-12-5

cyanide(1-)

thiocyanic acid
463-56-9

thiocyanic acid

Conditions
ConditionsYield
With ammonia; sulfur
cyanide(1-)
57-12-5

cyanide(1-)

selenocyanic acid
13103-11-2

selenocyanic acid

Conditions
ConditionsYield
With methanol; selenium at 0 - 25℃; Kinetik der Uebertragung;
cyanide(1-)
57-12-5

cyanide(1-)

bis-(1,1-dimethoxy-2,6-diphenyl-1λ5-phosphinin-4-yl)-methinium; tetrafluoroborate

bis-(1,1-dimethoxy-2,6-diphenyl-1λ5-phosphinin-4-yl)-methinium; tetrafluoroborate

bis-(1,1-dimethoxy-2,6-diphenyl-1λ5-phosphinin-4-yl)-acetonitrile
36374-67-1

bis-(1,1-dimethoxy-2,6-diphenyl-1λ5-phosphinin-4-yl)-acetonitrile

S-Phenyl benzenethiosulfonate
1212-08-4

S-Phenyl benzenethiosulfonate

cyanide(1-)
57-12-5

cyanide(1-)

A

phenyl thiocyanate
5285-87-0

phenyl thiocyanate

B

phenylsulphinate anion
16722-50-2

phenylsulphinate anion

Conditions
ConditionsYield
In water; acetonitrile at 25℃; Rate constant; tris/tris-H+ buffer;
(4S,4'R,5R)-2,2,2',2'-tetramethyl-5-((E)-2-nitrovinyl)-4,4'-bi(1,3-dioxolane)
110220-96-7

(4S,4'R,5R)-2,2,2',2'-tetramethyl-5-((E)-2-nitrovinyl)-4,4'-bi(1,3-dioxolane)

cyanide(1-)
57-12-5

cyanide(1-)

2-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acrylonitrile
118158-80-8

2-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acrylonitrile

Conditions
ConditionsYield
Yield given;

Cyanide Chemical Properties

Molecular Structure:

Molecular Formula: CN
Molecular Weight: 26.0179 
IUPAC Name: Cyanide
Synonyms of Cyanide (CAS NO.57-12-5): BRN 1900509 ; Carbon nitride ion (CN(sup 1-)) ; Carbon nitride ion (CN1-) ; Cyanide (CN(sup 1-)) ; Cyanide anion ; Cyanide ion ; Cyanide ions ; Cyanide(1-) ; Cyanide(1-) ion ; Cyanure ; Cyanure [French] ; Hydrocyanic acid, ion(1-)- ; Isocyanide ; Nitrile anion ; RCRA waste number P030 ; Cyanide (anion) ; Cyanide solutions, n.o.s. ; Cyanide solutions, n.o.s. [UN1935] [Poison, Keep away from food] ; Cyanides (soluble salts and complexes) not otherwise specified ; UN1935
CAS NO: 57-12-5
Classification Code: 2007 CERCLA Priority List, Rank: 28 ; Reportable Quantity (RQ) = 10 lb Boiling Point: 25.7 °C at 760 mmHg  
Index of Refraction: 1.262
Molar Refractivity: 6.41 cm3
Molar Volume: 38.8 cm3
Surface Tension: 18.8 dyne/cm
Density: 0.695 g/cm3
Enthalpy of Vaporization: 27.18 kJ/mol
Boiling Point: 25.7 °C at 760 mmHg
Vapour Pressure: 740 mmHg at 25°C

Cyanide Uses

 Cyanide (CAS NO.57-12-5) is mainly produced for the mining of gold and silver: it helps dissolve these metals and their ores. It is illegally used to capture live fish near coral reefs for the aquarium and seafood markets. It is also used as insecticides for fumigating ships.

Cyanide Production

 Cyanide (CAS NO.57-12-5) is produced by certain bacteria, fungi, and algae and are found in a number of foods and plants.

Cyanide Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 3mg/kg (3mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Nature. Vol. 228, Pg. 1315, 1970.

Cyanide Consensus Reports

  Cyanide (CAS NO.57-12-5) and its compounds are on the Community Right-To-Know List.

Cyanide Safety Profile

Very poisonous by most routes. Cyanide (CAS NO.57-12-5) directly stimulates the chemoreceptors of the carotid and aortic bodies with a resultant hyperpnea (increase in the depth and rate of respiration). Cardiac irregularities are often noted, but the heart invariably outlasts the respirations. Death is due to respiratory arrest of central origin. It can occur within seconds or minutes of the inhalation of high concentrations of HCN gas. Because of slower absorption, death may be more delayed after the ingestion of cyanide salts, but the critical events still occur within the first hour. Two other sources of cyanide have been responsible for human poisoning: the naturally occurring amygdalin and the drug nitroprusside.
Amygdalin is a cyanogenic glycoside found in apricot, peach, and similar fruit pits and in sweet almonds (Sayre and Kaymakcalan, 1941). It is a chemical combination of glucose, benzaldehyde, and cyanide from which the latter can be released by the action of β-glucosidase or emulsion. Although these enzymes are not found in mammalian tissues, the human intestinal microflora appears to possess these or similar enzymes capable of effecting cyanide release resulting in human poisoning. For this reason, amygdalin may be as much as 40 times more toxic by the oral route as compared with intravenous injection. Amygdalin is the major ingredient of Laetrile, and this alleged anticancer drug has also been responsible for human cyanide poisoning.
An ethical drug that may also cause cyanide poisoning in overdose is the potent vascular smooth-muscle relaxant sodium nitroprusside. Although nitroprusside is related chemically to ferricyanide, unlike the latter it penetrates into erythrocytes and reacts with hemoglobin to release its cyanide (Smith and Kruszyna, 1974). Fortunately, the therapeutic margin for nitroprusside appears to be quite large.
 Cyanide is commonly found in certain rat and pest poisons, silver and metal polishes, photographic solutions, and fumigating products. Compounds such as potassium cyanide can also be readily purchased from chemical stores. Cyanide is readily absorbed from all routes, including the skin, mucous membranes, and by inhalation, although alkali salts of cyanide are toxic only when ingested. Death may occur with ingestion of even small amounts of sodium or potassium cyanide and can occur within minutes or hours depending on route of exposure. Inhalation of toxic fumes represents a potentially rapidly fatal type of exposure. A blood cyanide level of greater than 0.2 µg/mL is considered toxic. Lethal cases have usually had levels above 1 µg/mL.
Clinically, cyanide poisoning is reported to produce a bitter, almond odor on the breath of the patient; however, only a small proportion of the population is genetically able to discern this characteristic odor. Typically, cyanide has a bitter, burning taste, and, following poisoning, symptoms of salivation, nausea without vomiting, anxiety, confusion, vertigo, giddiness, lower-jaw stiffness, convulsions, opisthotonos, paralysis, coma, cardiac arrhythmias, and transient respiratory stimulation followed by respiratory failure may occur. Bradycardia is a common finding, but in most cases heartbeat usually outlasts respiration (Wexler et al., 1947). A prolonged expiratory phase is considered to be characteristic of cyanide poisoning. (Casarett and Doull's, Toxicology, The Basic Science of Poisons 2nd ed. Doull, Klaassen and Amdur (eds), Macmillan Pub. Co. Inc. New York, NY).
The volatile cyanides resemble HCN physiologically, inhibiting tissue oxidation and causing death through asphyxia. Cyanogen is probably as toxic as HCN; the nitriles are generally considered somewhat less toxic, probably because of their lower volatility. The non-volatile cyanide salts appear to be relatively nontoxic systemically, so long as they are not ingested and care is taken to prevent the formation of HCN. Workers, such as electroplaters and picklers, who are daily exposed to cyanide solutions may develop a “cyanide” rash, characterized by itching, and by macular, papular, and vesicular eruptions. Frequently there is secondary infection. Exposure to small amounts of cyanide compounds over long periods of time is reported to cause loss of appetite, headache, weakness, nausea, dizziness, and symptoms of irritation of the upper respiratory tract and eyes. See also specific cyanide compounds.
Flammable by chemical reaction with heat, moisture, acid. Many cyanides rather easily evolve HCN, a flammable gas that is highly toxic. Carbon dioxide from the air is sufficiently acidic to liberate HCN from cyanide solutions. Reaction with hypochlorite solutions may be violent at pH 10.0–10.3. Cyanides explode if melted with nitrites or chlorates at about 450°. Violent reaction with F2, Mg, nitrates, HNO3, nitrites. Metal cyanides are easily oxidized and may be thermally unstable. N-cyano derivatives may be reactive or unstable. Many organic nitriles can be very reactive under the right conditions. When heated to decomposition or on contact with acid, acid fumes, water, or steam, cyanides emit toxic and flammable vapors of CN. See also HYDROCYANIC ACID.

Cyanide Standards and Recommendations

OSHA PEL: TWA 5 mg(CN)/m3
ACGIH TLV: CL 5 mg/m3 (skin)
DFG MAK: 5 mg/m3
NIOSH REL: (Cyanide) TWA CL 5 mg/m3/10M
DOT Classification:  6.1; Label: Poison, KEEP AWAY FROM FOOD

Cyanide Analytical Methods

For occupational chemical analysis use OSHA: #ID-120 or NIOSH: Cyanides (Aerosol and Gas) 7904.

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