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143-33-9

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143-33-9 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 143-33-9 differently. You can refer to the following data:
1. Sodium cyanide is a white crystalline solid that is odourless when dry but emits a slight odour of HCN in damp air. It is slightly soluble in ethanol and formamide. It is very poisonous. It explodes if melted with nitrite or chlorate at about 450°F. It produces a violent reaction with magnesium, nitrites, nitrates, and nitric acid. On contact with acid, acid fumes, water, or steam, it will produce toxic and flammable vapours.for the extraction of gold and silver ore, copper, zinc, carburizing, medicine and so on. For metallurgy, steel quenching, electroplating, extraction (forming cyanide), organic synthesis of raw materials, insecticidal and anti-corrosion.
2. Sodium cyanide is found as white granules, flakes or lumps. Sodium cyanide is shipped as pellets or briquettes. Odorless when dry. It absorbs water from air (is hygroscopic or deliquescent). Hydrogen cyanide gas released by sodium cyanide has a distinctive mild, bitter almond odor, but a large proportion of people cannot detect it; the odor does not provide adequate warning of hazardous concentrations.

Toxicity

Sodium cyanide binds to the ferric iron of oxidized cytochrome oxidase, disabling its ability to deliver oxygen, resulting in tissue hypoxia, "intracellular asphyxia." Rat: oral administration-LD50: 6.44mg / kg, adult lethal dose 200mg. Being highly toxic. It can be absorbed through the respiratory tract, digestive tract and skin. Animals, after inhaling sodium cyanide aerosol of 40mg-90mg / m3, get symptoms of irritations, irritability and salivation after 25 to 43 minutes. Inhalation of 150mg ~ 170mg / m3 for 62 to 76 minutes or inhalation of 400mg ~ 500mg / m3 for 20 minutes can cause death. Human oral LD50 is about 1mg ~ 2mg / kg. Under normal conditions of production, sodium cyanide dust is often inhaled at room temperature, and sodium vapor can be inhaled during heat treatment. Misdiagnosis is also one of the common causes of poisoning. In the event of a fire, try to prevent the generation of toxic hydrogen cyanide gas. Do not use carbon dioxide or acid-base foam fire extinguishers. Fire-fighting operation personnel must wear protective equipment, try not to contact with water containing sodium cyanide. This product is toxic with poisoning causing dizziness and other uncomfortable symptoms. When found, patients should immediately leave the contaminated area to the fresh air and taken 1% soda solution as first aid, at the same time, go to the hospital for treatment. UN No.: 1689/6257 / 6.1-04 / 215.

Uses

Different sources of media describe the Uses of 143-33-9 differently. You can refer to the following data:
1. For the extraction of gold and silver from ores; gold (or silver) reacts with sodium cyanide in the presence of air to form the complex sodium cyanurate, which dissolves the gold from the ore. Further reaction with zinc can displace gold, generating sodium cyanate and free the gold out. 4Au + 8NaCN + O2 + 2H2O → 4Na [Au (CN) 2] + 4NaOH Na [Au (CN) 2] + Zn → Na [Zn (CN) 3] + Au Others can also be used for iron blue (intermediate sodium ferrocyanide production), cyanuric chloride (intermediate product of cyanide production), plating bath (copper, cadmium and other plating, DL-methionine synthesis). It can act as liquid steel carburizing agent with barium chloride (usually accompanied with a bath temperature of 800 °C or more; should add salts that don’t cause NaCN evaporation at high temperature) , and for pesticides and other purposes.
2. Sodium cyanide is used as a starting material for the preparation of Reissert compounds, cyanogen bromide, cyanuric chloride and cyanogen chloride. It acts as a catalyst for the aminolysis of esters to primary amides. Furthermore, it is used for fumigation, in electroplating and for extracting gold and silver in mining industry. In organic synthesis, it is involved in the cyanation reaction of alkyl halides under phase transfer conditions.
3. Extracting gold and silver from ores; electroplating baths; case hardening steel by liquid nitriding; manufacture of hydrocyanic acid and other cyanides.
4. Sodium cyanide is used for electroplating metals such as zinc, copper, cadmium, silver, and gold, and their alloys; for extracting gold and silver from ores; and as a fumigant and a chelating agent. It occurs in many varieties of maniocs (cassava), especially in bitter manioc.

Preparation

Different sources of media describe the Preparation of 143-33-9 differently. You can refer to the following data:
1. 1.(Castner improved method) sodium metal and ammonia as raw material to generate sodium amide, and then subjects to carbon reduction at 700 ~ 800 ℃to obtain the product [1]. 2Na + 2NH3 → 2NaNH2 + H2 NaNH2 + C → [1] + H2 2. Natural gas (methane), ammonia, air as raw materials; their mixture is passed through the catalyst bed at 1000 ℃to generate hydrogen cyanide, followed by reaction with sodium hydroxide to obtain it [1]. HCN + NaOH → [1] + H2O 3. Hydrogen cyanide can obtained as byproduct during ammonia oxidation of propylene to generate acrylonitrile [1].
2. Sodium cyanide can be prepared by several methods (See Potassium Cyanide).It is prepared by passing hydrogen cyanide through a 50% aqueous solution of sodium hydroxide followed by evaporation of the solution in vacuum: NaOH + HCN → NaCN + H2OAnother method is to reduce sodamide with carbon at red heat: NaNH2 + C → NaCN + H2↑Also, sodium cyanide can be made by heating a mixture of sodium carbonate and carbon with ammonia at high temperatures: Na2CO3 + 4C + 2NH3 → 2NaCN + 3CO↑ + 3H2↑.

Description

Sodium cyanide, NaCN, is a cyanide salt that is a white, deliquescent, crystalline powder and is soluble in water. The specific gravity is 1.6, which is heavier than water. Sodium cyanide is toxic by inhalation and ingestion, with a TLV of 4.7 ppm and 5 mg/m3 of air. The target organs are the cardiovascular system, central nervous system, kidneys, liver, and skin. Reactions with acids can release flammable and toxic hydrogen cyanide gas. Cyanides are incompatible with all acids. The four-digit UN identification number is 1689. The NFPA 704 designation is health 3, flammability 0, and reactivity 0. The primary uses are in gold and silver extraction from ores, electroplating, fumigation, and insecticides.

Physical properties

Physical Properties White cubic crystals; hygroscopic; density 1.6 g/cm3; melts at 563°C; very soluble in water; aqueous solution strongly alkaline and decomposes rapidly.

Production Methods

Sodium cyanide was first prepared in 1834 by heating Prussian Blue, a mixture of cyanogen compounds of iron, and sodium carbonate and extracting sodium cyanide from the cooled mixture using alcohol. Sodium cyanide remained a laboratory curiosity until 1887, when a process was patented for the extraction of gold and silver ores by means of a dilute solution of cyanide.

Definition

sodium cyanide: A white orcolourless crystalline solid, NaCN,deliquescent, soluble in water and inliquid ammonia, and slightly solublein ethanol; cubic; m.p. 564°C; b.p.1496°C. Sodium cyanide is now madeby absorbing hydrogen cyanide insodium hydroxide or sodium carbonatesolution. The compound is extremelypoisonous because it reacts with the iron in haemoglobin in theblood, so preventing oxygen reachingthe tissues of the body. It is used inthe extraction of precious metals andin electroplating industries. Aqueoussolutions are alkaline due to salt hydrolysis.

Reactions

Sodium cyanide, NaCN, white solid, soluble, very poisonous, formed (1) by reaction of sodamide and carbon at high temperature, (2) by reaction of calcium cyanamide and sodium chloride at high temperature, reacts in dilute solution in air with gold or silver to form soluble sodium gold or silver cyanide, and used for this purpose in the cyanide process for recovery of gold. The percentage of available cyanide is greater than in potassium cyanide previously used. Used as a source of cyanide, and for hydrocyanic acid.

General Description

A clear colorless aqueous solution.

Air & Water Reactions

Slowly evolves flammable and poisonous hydrogen cyanide gas.

Reactivity Profile

Sodium cyanide is weakly basic. Reacts with acids of all kinds to generate quantities of very poisonous hydrogen cyanide gas. Incompatible with strong oxidizing agents, especially if solution dries out. Gives insoluble products with silver(I), mercury(I) and lead(II) ions that may decompose violently under certain conditions.

Hazard

Toxic by ingestion and inhalation.

Health Hazard

Different sources of media describe the Health Hazard of 143-33-9 differently. You can refer to the following data:
1. Sodium cyanide is a highly poisonous compound by oral intake and by ocular and skin absorption. Accidental ingestion of a small quantity; as low as 100–150 mg could result in immediate collapse and instantaneous death in humans. At a lower dosage it can cause nausea, vomiting, hallucination, headache, and weakness. The toxicology of NaCN is the same as that of HCN. The metal cyanide forms HCN rapidly in the body, causing immediate death from a high dosage. The lethal effect from cyanide poisoning varied with species. Investigating the acute oral toxicity of sodium cyanide in birds, Wiemeyer et al. (1986) observed that the LD50 values for the flesh-eating birds were lower than that for the birds that fed on plant material; vulture 4.8 mg/kg versus chicken 21 mg/kg. In a study on marine species, Pavicic and Pihlar (1983) found that at 10 ppm concentration of NaCN, invertebrates were more sensitive than fishes. In animals, the lethal dose of NaCN were in the same range by different toxic routes. A dose of 8 mg NaCN/kg resulted in ataxia, immobilization, and death in coyotes (Sterner 1979); however, the lethal time was longer, at 18 minutes. Ballantyne (1983b) studied the acute lethal toxicity of sodium and other cyanides by ocular route. He found that cyanide instilled into the eye was absorbed across conjunctival blood vessels causing systemic toxicity and death within 3–12 minutes of the eye being contaminated. The toxicity of the cyanide did not decrease by mixing the solid with an inert powder such as kaolin. LD50 value, intraperitoneal (mice): 4.3 mg/kg LD50 value, oral (rats): 6.4 mg/kg Sodium cyanide is a teratogen, causing fetus damage and developmental abnormalities in the cardiovascular system in hamsters (NIOSH 1986). Sodium cyanide reacts with acids to form highly toxic hydrogen cyanide. There could be a slow liberation of HCN in contact with water.
2. Sodium cyanide is a white crystalline solid that is odorless when dry, but emits a slight odor of hydrogen cyanide in damp air. It is slightly soluble in ethanol and formamide. It is very poisonous. It explodes if melted with nitrite or chlorate at about 450°F. It produces a violent reaction with magnesium, nitrites, nitrates, and nitric acid. On contact with acid, acid fumes, water, or steam, it produces toxic and flammable vapors. Synonyms for sodium cyanide are hydrocyanic acid, sodium salt, and cyanide of sodium.

Flammability and Explosibility

Sodium cyanide and potassium cyanide are noncombustible solids. Reaction with acids liberates flammable HCN.

Industrial uses

sodium cyanide and other water-soluble cyanides are used as modifying reagents for selective flotation of ores containing galena, sphalerite and gangue minerals.

Safety Profile

A deadly human poison by ingestion. A deadly experimental poison by ingestion, intraperitoneal, subcutaneous, intravenous, parenteral, intramuscular, and ocular routes. An experimental teratogen. Human systemic effects by ingestion: hallucinations, dstorted perceptions, muscle weakness, and gastritis. Experimental reproductive effects. hydrocyanic acid physiologically, inhibiting tissue oxidation and causing death through asphyxia. Cyanogen is probably as toxic as hydrocyanic acid; the nitriles are generally considered somewhat less toxic, probably because of their lower volathty. The nonvolaule cyanide salts appear to be relatively nonhazardous systemically, so long as they are not ingested and care is taken to prevent the formation of hydrocyanic acid. 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. moisture, acid. Many cyanides evolve hydrocyanic acid rather easily. This is a flammable gas and is highly toxic. Carbon dioxide from the air is sufficiently acidc to liberate hydrocyanic acid from cyanide solutions. Explodes if melted with nitrite or chlorate @ about 450”. Violent reaction with F2, Mg, nitrates, HNO3, nitrites. Upon contact with acid, acid fumes, water, or steam, it wdl produce toxic and flammable vapors of CNand NanO. Used in the extraction of gold and silver ores, in electroplating, and in insecticides. See also CYANIDE and HYDROCYANIC ACID, The volaule cyanides resemble Flammable by chemical reaction with heat,

Potential Exposure

Sodium cyanide is used as a solid or in solution to extract metal ores, in electroplating and metal cleaning baths; in metal hardening; in treatment of rabbit and rat burrows and holes and termite nests; in insecticides

storage

In particular, work with cyanides should be conducted in a fume hood to prevent exposure by inhalation, and splash goggles and impermeable gloves should be worn at all times to prevent eye and skin contact. Cyanide salts should be stored in a cool, dry location, separated from acids.

Shipping

UN1689 Sodium cyanide, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Incompatibilities

Sodium cyanide decomposes on contact with acids, acid salts, water, moisture, alcohols, and carbon dioxide, releasing highly toxic and flammable hydrogen cyanide gas. Aqueous solution is a strong base; it reacts violently with acid and is corrosive. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Absorbs moisture from the air forming a corrosive syrup. Corrosive to active metals, such as aluminum, copper, and zinc. Under acid conditions, sarin hydrolyzes to form hydrofluoric acid.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Add strong alkaline hypochlorite and react for 24 hours. Then flush to sewer with large volumes of water.

Check Digit Verification of cas no

The CAS Registry Mumber 143-33-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 3 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 143-33:
(5*1)+(4*4)+(3*3)+(2*3)+(1*3)=39
39 % 10 = 9
So 143-33-9 is a valid CAS Registry Number.
InChI:InChI=1/CN.Na/c1-2;/rCNNa/c2-1-3

143-33-9Synthetic route

α-benzyloxy-α-phenyl-as-triazine-5-acetonitrile
107126-37-4

α-benzyloxy-α-phenyl-as-triazine-5-acetonitrile

A

sodium cyanide
143-33-9

sodium cyanide

B

5-benzoyl-6-methyl-3-phenyl-as-triazine
107126-34-1

5-benzoyl-6-methyl-3-phenyl-as-triazine

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With sodium hydroxide In water; dimethyl sulfoxideA n/a
B 54%
C n/a
methanol
67-56-1

methanol

benzo[d]thiazol-2-yl thiocyanate
6011-99-0

benzo[d]thiazol-2-yl thiocyanate

sodium cyanide
143-33-9

sodium cyanide

Conditions
ConditionsYield
at 22 - 27℃;
at 22 - 27℃;
diethyl ether
60-29-7

diethyl ether

bromocyane
506-68-3

bromocyane

sodium diethylmalonate
996-82-7

sodium diethylmalonate

A

diethyl 2-cyanomalonate
4513-67-1

diethyl 2-cyanomalonate

B

1,1,2,2-tetracarboethoxy-ethylene
6174-95-4

1,1,2,2-tetracarboethoxy-ethylene

C

tetraethyl ethane-1,1,2,2-tetracarboxylate
632-56-4

tetraethyl ethane-1,1,2,2-tetracarboxylate

D

sodium cyanide
143-33-9

sodium cyanide

bromocyane
506-68-3

bromocyane

ethanol
64-17-5

ethanol

sodium diethylmalonate
996-82-7

sodium diethylmalonate

A

diethyl 2-cyanomalonate
4513-67-1

diethyl 2-cyanomalonate

B

1,1,2,2-tetracarboethoxy-ethylene
6174-95-4

1,1,2,2-tetracarboethoxy-ethylene

C

tetraethyl ethane-1,1,2,2-tetracarboxylate
632-56-4

tetraethyl ethane-1,1,2,2-tetracarboxylate

D

sodium cyanide
143-33-9

sodium cyanide

bromocyane
506-68-3

bromocyane

ethanol
64-17-5

ethanol

sodium diethylmalonate
996-82-7

sodium diethylmalonate

A

1,1,2,2-tetracarboethoxy-ethylene
6174-95-4

1,1,2,2-tetracarboethoxy-ethylene

B

sodium cyanide
143-33-9

sodium cyanide

hydrogen cyanide
74-90-8

hydrogen cyanide

sodium ethanolate
141-52-6

sodium ethanolate

sodium cyanide
143-33-9

sodium cyanide

hydrogen cyanide
74-90-8

hydrogen cyanide

sodium formate
141-53-7

sodium formate

sodium cyanide
143-33-9

sodium cyanide

hydrogen cyanide
74-90-8

hydrogen cyanide

sodium cyanide
143-33-9

sodium cyanide

Conditions
ConditionsYield
With sodium hydroxide
With sodium hydroxide; ethanol
With sodium hydroxide at 200 - 300℃;
diethyl oximidate
13534-15-1, 88770-07-4

diethyl oximidate

sodium ethanolate
141-52-6

sodium ethanolate

A

diethyl imidocarbonate
2812-77-3

diethyl imidocarbonate

B

sodium cyanide
143-33-9

sodium cyanide

ethyl 2-ethoxy-2-iminoacetate
816-27-3

ethyl 2-ethoxy-2-iminoacetate

sodium ethanolate
141-52-6

sodium ethanolate

A

sodium cyanide
143-33-9

sodium cyanide

B

Diethyl carbonate
105-58-8

Diethyl carbonate

benzoyloxyacetonitrile
939-56-0

benzoyloxyacetonitrile

sodium ethanolate
141-52-6

sodium ethanolate

A

sodium benzoate
532-32-1

sodium benzoate

B

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

C

sodium cyanide
143-33-9

sodium cyanide

1-hydroxy-2-isopropyl-5-methyl-cyclohexanecarbonitrile
100400-22-4

1-hydroxy-2-isopropyl-5-methyl-cyclohexanecarbonitrile

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

sodium cyanide
143-33-9

sodium cyanide

B

Menthone
10458-14-7

Menthone

sodium formate
141-53-7

sodium formate

sodium cyanide
143-33-9

sodium cyanide

Conditions
ConditionsYield
With sodium amide at 620℃;
sodium acetylide

sodium acetylide

A

sodium cyanide
143-33-9

sodium cyanide

Conditions
ConditionsYield
With ammonia at 500℃;
sodium formaldoximate
61706-59-0

sodium formaldoximate

sodium cyanide
143-33-9

sodium cyanide

Conditions
ConditionsYield
bei der Explosion;
benzyl-malononitrile; sodium-compound

benzyl-malononitrile; sodium-compound

A

sodium cyanide
143-33-9

sodium cyanide

B

dihydrocinnamonitrile
645-59-0

dihydrocinnamonitrile

methyl thiocyanate
556-64-9

methyl thiocyanate

sodium diethyl phosphite
2303-76-6, 118080-94-7

sodium diethyl phosphite

toluene
108-88-3

toluene

A

O,O,S-trimethyl phosphorothioate
152-20-5

O,O,S-trimethyl phosphorothioate

B

sodium cyanide
143-33-9

sodium cyanide

sodium ethanolate
141-52-6

sodium ethanolate

ethyl cyanoformate
623-49-4

ethyl cyanoformate

A

sodium cyanide
143-33-9

sodium cyanide

B

Diethyl carbonate
105-58-8

Diethyl carbonate

4-cyano-1,4-dihydro-N-methylpyridine-3-carboxamide
19432-60-1

4-cyano-1,4-dihydro-N-methylpyridine-3-carboxamide

A

sodium cyanide
143-33-9

sodium cyanide

B

1-methylnicotinamide chloride
1005-24-9

1-methylnicotinamide chloride

Conditions
ConditionsYield
at 25℃; Equilibrium constant; reaction in reversed-micellar system H2O/ HTAB/ CHCl3-isooctane, diff. molar ratios H2O/ HTAB, other temp.;
cyanogen iodide
506-78-5

cyanogen iodide

sodium cyanide
143-33-9

sodium cyanide

Conditions
ConditionsYield
With iodide In ethanol at 30℃; Equilibrium constant; buffer solvent (CH3CO2Na, CH3CO2H);
1,3-diphenyl-2-oximino-1,3-propanedione
51210-89-0

1,3-diphenyl-2-oximino-1,3-propanedione

A

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

B

sodium cyanide
143-33-9

sodium cyanide

C

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With sodium ethanolate In ethanol Product distribution;
hexadecyltrimethylammonium cyanide
74784-26-2

hexadecyltrimethylammonium cyanide

A

sodium cyanide
143-33-9

sodium cyanide

B

cetyltrimethylammonim bromide
57-09-0

cetyltrimethylammonim bromide

Conditions
ConditionsYield
With sodium bromide In water at 20℃; Equilibrium constant;
2,4,6-triamino-s-triazine
108-78-1

2,4,6-triamino-s-triazine

sodium amide

sodium amide

coal

coal

sodium cyanide
143-33-9

sodium cyanide

Conditions
ConditionsYield
at 750 - 850℃; beim Zusammenschmelzen;
at 750 - 850℃; beim Zusammenschmelzen;
(5-methyl-1-phenyl-1H-pyrazol-4-yl)-glyoxal oxime

(5-methyl-1-phenyl-1H-pyrazol-4-yl)-glyoxal oxime

diluted NaOH-solution

diluted NaOH-solution

A

sodium cyanide
143-33-9

sodium cyanide

B

1-phenyl-5-methyl-pyrazole-carboxylic acid-(4)

1-phenyl-5-methyl-pyrazole-carboxylic acid-(4)

9-formohydroximoyl-6-hydroxy-xanthen-3-one

9-formohydroximoyl-6-hydroxy-xanthen-3-one

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

sodium cyanide
143-33-9

sodium cyanide

B

3.6-dioxy-xanthone

3.6-dioxy-xanthone

ethanol
64-17-5

ethanol

phenylacetonitrile
140-29-4

phenylacetonitrile

sodium

sodium

A

sodium cyanide
143-33-9

sodium cyanide

B

ammonia
7664-41-7

ammonia

benzo[d]thiazol-2-yl thiocyanate
6011-99-0

benzo[d]thiazol-2-yl thiocyanate

sodium 2-mercaptobenzothiazole
2492-26-4

sodium 2-mercaptobenzothiazole

boiling benzene

boiling benzene

A

2,2'-thiobis(benzothiazole)
4074-77-5

2,2'-thiobis(benzothiazole)

B

di(benzothiazol-2-yl)disulfide
120-78-5

di(benzothiazol-2-yl)disulfide

C

sodium cyanide
143-33-9

sodium cyanide

D

sodium thiocyanide
540-72-7

sodium thiocyanide

sodium amide

sodium amide

methylamine
74-89-5

methylamine

sodium cyanide
143-33-9

sodium cyanide

Conditions
ConditionsYield
at 250℃;
sodium amide

sodium amide

N-Cyanoguanidine
127099-85-8, 780722-26-1

N-Cyanoguanidine

coal

coal

sodium cyanide
143-33-9

sodium cyanide

Conditions
ConditionsYield
at 750 - 850℃; beim Zusammenschmelzen;
acetonitrile
75-05-8

acetonitrile

sodium

sodium

A

sodium cyanide
143-33-9

sodium cyanide

B

'kyanmethine'

'kyanmethine'

sodium cyanide
143-33-9

sodium cyanide

2-chloromethyl-1,3,5-trimethylbenzene
1585-16-6

2-chloromethyl-1,3,5-trimethylbenzene

mesitylacetonitrile
34688-71-6

mesitylacetonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide at 80℃; for 0.5h; Substitution;100%
Stage #1: sodium cyanide In ethanol; water Heating / reflux;
Stage #2: 2-chloromethyl-1,3,5-trimethylbenzene In ethanol; water for 3h; Heating / reflux;
72%
In ethanol
sodium cyanide
143-33-9

sodium cyanide

4-(chloromethyl)-1,2-dimethylbenzene
102-46-5

4-(chloromethyl)-1,2-dimethylbenzene

3,4-dimethylphenylacetonitrile
3020-06-2

3,4-dimethylphenylacetonitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 16h;100%
In ethanol
In ethanol Heating;
furfural
98-01-1

furfural

sodium cyanide
143-33-9

sodium cyanide

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

carbonic acid, cyano(2-furyl)methyl ethyl ester
20893-23-6

carbonic acid, cyano(2-furyl)methyl ethyl ester

Conditions
ConditionsYield
With tetrabutyl-ammonium chloride In dichloromethane; water Heating;100%
10-Chloro-5H-benzoxazole<3,2-a>quinolin-5-one
54475-84-2

10-Chloro-5H-benzoxazole<3,2-a>quinolin-5-one

sodium cyanide
143-33-9

sodium cyanide

1-(5-chloro-2-hydroxyphenyl)-1,4-dihydro-4-oxo-2-quinolinecarbonitrile
80990-60-9

1-(5-chloro-2-hydroxyphenyl)-1,4-dihydro-4-oxo-2-quinolinecarbonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide at 120℃; for 0.5h;100%
bis (2-chloroethyl) sulphide
505-60-2

bis (2-chloroethyl) sulphide

sodium cyanide
143-33-9

sodium cyanide

3,3'-thiobis-propanenitrile
111-97-7

3,3'-thiobis-propanenitrile

Conditions
ConditionsYield
With benzyltri(n-butyl)ammonium chloride In water at 80℃; for 3h;100%
trans-4,5-bis(hydroxymethyl)cyclohexene bis(toluene-p-sulfonate)
7500-58-5, 20246-03-1, 20518-14-3, 32970-96-0, 60894-68-0

trans-4,5-bis(hydroxymethyl)cyclohexene bis(toluene-p-sulfonate)

sodium cyanide
143-33-9

sodium cyanide

(+/-)-(trans-cyclohex-4-ene-1,2-diyl)-di-acetonitrile
119595-00-5

(+/-)-(trans-cyclohex-4-ene-1,2-diyl)-di-acetonitrile

Conditions
ConditionsYield
In ethanol for 72h; Heating;100%
sodium cyanide
143-33-9

sodium cyanide

dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on
6616-69-9, 16964-48-0, 16964-51-5, 52195-11-6, 60761-09-3, 63790-37-4, 138383-58-1

dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on

(trans-rac)-6a,7,8,9,10,10a-hexahydro-1,9-dihydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carbonitrile
105539-71-7, 105539-72-8, 121657-71-4

(trans-rac)-6a,7,8,9,10,10a-hexahydro-1,9-dihydroxy-6,6-dimethyl-3-pentyl-6H-dibenzopyran-9-carbonitrile

Conditions
ConditionsYield
In methanol for 2h; Ambient temperature;100%
sodium cyanide
143-33-9

sodium cyanide

1-(bromomethyl)-4-methyl-2-(phenylmethoxy)benzene
117571-35-4

1-(bromomethyl)-4-methyl-2-(phenylmethoxy)benzene

<4-methyl-2-(phenylmethoxy)phenyl>acetonitrile
117571-36-5

<4-methyl-2-(phenylmethoxy)phenyl>acetonitrile

Conditions
ConditionsYield
With tetrabutylammomium bromide In dichloromethane; water at 20℃; for 1h;100%
tetrabutylammomium bromide In dichloromethane; water at 20℃; for 15h;
sodium cyanide
143-33-9

sodium cyanide

6-chloro-9-thiabicyclo<3.3.1>non-2-ene
6522-22-1, 14697-77-9

6-chloro-9-thiabicyclo<3.3.1>non-2-ene

9-thiabicyclo<3.3.1>non-2-ene-6-carbonitrile
6435-98-9, 74830-38-9

9-thiabicyclo<3.3.1>non-2-ene-6-carbonitrile

Conditions
ConditionsYield
With 18-crown-6 ether In chloroform for 4h; Heating;100%
In water; acetone for 20h; Heating;71%
sodium cyanide
143-33-9

sodium cyanide

2-(chloromethyl)-1-methoxy-4-(2-methoxyethyl)benzene
80314-64-3

2-(chloromethyl)-1-methoxy-4-(2-methoxyethyl)benzene

<2'-methoxy-5'-(2''-methoxyethyl)phenyl>acetonitrile
80314-59-6

<2'-methoxy-5'-(2''-methoxyethyl)phenyl>acetonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide100%
In dimethyl sulfoxide at 42.5℃; for 3h;100%
sodium cyanide
143-33-9

sodium cyanide

6-benzyloxy-4-methyl-4Z-hexen-1-ol p-toluenesulfonate
73454-44-1

6-benzyloxy-4-methyl-4Z-hexen-1-ol p-toluenesulfonate

(Z)-7-benzyloxy-5-methyl-5-heptenenitrile
73454-49-6

(Z)-7-benzyloxy-5-methyl-5-heptenenitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 98℃; for 24h;100%
sodium cyanide
143-33-9

sodium cyanide

ethyl N-<2-(bromoacetyl)phenyl>carbamate
122807-12-9

ethyl N-<2-(bromoacetyl)phenyl>carbamate

1,4-bis(2-ethoxycarbonylaminophenyl)-2-cyano-1,4-butanedione
138768-58-8

1,4-bis(2-ethoxycarbonylaminophenyl)-2-cyano-1,4-butanedione

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 1h; Ambient temperature;100%
sodium cyanide
143-33-9

sodium cyanide

8-methoxy-5-<2'-(2''-methyl-1'',3''-dioxolan-2''-yl)ethyl>-3,4-dihydronaphthalen-2(1H)-one
80535-58-6

8-methoxy-5-<2'-(2''-methyl-1'',3''-dioxolan-2''-yl)ethyl>-3,4-dihydronaphthalen-2(1H)-one

2-hydroxy-8-methoxy-5-<2'-(2-1,2,3,4-tetrahydronaphthalene-2-carbonitrile" src="//file1.lookchem.com/cas/reactions/2021/05/29/5100346.png_ms" />
80535-46-2

2-hydroxy-8-methoxy-5-<2'-(2"-methyl-1",3"-dioxolan-2"-yl)ethyl>-1,2,3,4-tetrahydronaphthalene-2-carbonitrile

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water100%
sodium cyanide
143-33-9

sodium cyanide

Toluene-4-sulfonic acid 6-methyl-1,4-dithia-spiro[4.5]dec-8-ylmethyl ester

Toluene-4-sulfonic acid 6-methyl-1,4-dithia-spiro[4.5]dec-8-ylmethyl ester

4-cyanomethyl-1,1-ethylenedithio-2-methylcyclohexane
76235-43-3

4-cyanomethyl-1,1-ethylenedithio-2-methylcyclohexane

Conditions
ConditionsYield
In dimethyl sulfoxide100%
sodium cyanide
143-33-9

sodium cyanide

Toluene-4-sulfonic acid (5E,7E)-(R)-4-methyl-undeca-5,7-dienyl ester
115094-15-0

Toluene-4-sulfonic acid (5E,7E)-(R)-4-methyl-undeca-5,7-dienyl ester

(R)-1-cyano-4-methyl-(E,E)-5,7-undecadiene
115094-13-8

(R)-1-cyano-4-methyl-(E,E)-5,7-undecadiene

Conditions
ConditionsYield
In dimethyl sulfoxide at 80 - 85℃; for 3.5h;100%
sodium cyanide
143-33-9

sodium cyanide

2-(2-formamidophenyl)adamantan-2-ol
82757-18-4

2-(2-formamidophenyl)adamantan-2-ol

2-(2-aminophenyl)-2-cyanoadamantane
82757-22-0

2-(2-aminophenyl)-2-cyanoadamantane

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 120h;100%
In N,N-dimethyl-formamide at 80℃;100%
sodium cyanide
143-33-9

sodium cyanide

(2R,3S,4E)-(-)-(3-Methoxy-2-methyl-5-phenyl-4-pentenyl)-p-toluolsulfonat
90664-12-3

(2R,3S,4E)-(-)-(3-Methoxy-2-methyl-5-phenyl-4-pentenyl)-p-toluolsulfonat

(3R,4R,5E)-(+)-4-Methoxy-3-methyl-6-phenyl-5-hexennitril
90664-13-4

(3R,4R,5E)-(+)-4-Methoxy-3-methyl-6-phenyl-5-hexennitril

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 115℃; for 0.666667h;100%
sodium cyanide
143-33-9

sodium cyanide

Benzoic acid (2R,3S)-2-methoxy-3-methyl-4-trimethylsilanyloxy-butyl ester

Benzoic acid (2R,3S)-2-methoxy-3-methyl-4-trimethylsilanyloxy-butyl ester

(3S,4R)-5-benzyloxy-4-methoxy-3-methylpentanenitrile
141546-69-2

(3S,4R)-5-benzyloxy-4-methoxy-3-methylpentanenitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 50℃; for 6h;100%
sodium cyanide
143-33-9

sodium cyanide

11,12-dicyano-9,10-anthraquinodimethane
93645-46-6

11,12-dicyano-9,10-anthraquinodimethane

9-(dicyanomethyl)-10-cyanomethylanthracene
93645-47-7

9-(dicyanomethyl)-10-cyanomethylanthracene

Conditions
ConditionsYield
In 1,4-dioxane; ethanol for 24h; Heating;100%
sodium cyanide
143-33-9

sodium cyanide

1-[4-(9-Bromo-nonyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone
79557-82-7

1-[4-(9-Bromo-nonyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone

10-(4-Acetyl-3-hydroxy-2-propylphenoxy)decane nitrile
92518-11-1

10-(4-Acetyl-3-hydroxy-2-propylphenoxy)decane nitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 75 - 85℃; for 17h;100%
sodium cyanide
143-33-9

sodium cyanide

1-[4-(10-Bromo-decyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone
106627-35-4

1-[4-(10-Bromo-decyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone

11-(4-Acetyl-3-hydroxy-2-propyl-phenoxy)-undecanenitrile
92518-12-2

11-(4-Acetyl-3-hydroxy-2-propyl-phenoxy)-undecanenitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 75 - 85℃; for 17h;100%
sodium cyanide
143-33-9

sodium cyanide

4-O-benzoyl-2-deoxy-1-O-methylsulfonyl-2-C-methyl-3-O-methyl-L-threitol
141546-68-1

4-O-benzoyl-2-deoxy-1-O-methylsulfonyl-2-C-methyl-3-O-methyl-L-threitol

(3S,4R)-5-benzyloxy-4-methoxy-3-methylpentanenitrile
141546-69-2

(3S,4R)-5-benzyloxy-4-methoxy-3-methylpentanenitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 50℃; for 6h;100%
sodium cyanide
143-33-9

sodium cyanide

(+/-)-2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranethanol p-toluenesulfonate
154954-44-6

(+/-)-2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranethanol p-toluenesulfonate

(+/-)-β-(2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranyl)propionitrile
154954-45-7

(+/-)-β-(2,3-dihydro-5-methoxy-4,6,7-trimethyl-2-benzofuranyl)propionitrile

Conditions
ConditionsYield
In ethanol; N,N-dimethyl-formamide for 1.5h; Heating;100%
sodium cyanide
143-33-9

sodium cyanide

2-(bromomethyl)-11H-dibenzo<1,4>dioxepin
102492-60-4

2-(bromomethyl)-11H-dibenzo<1,4>dioxepin

11H-dibenzo<1,4>dioxepin-2-acetonitrile
102492-61-5

11H-dibenzo<1,4>dioxepin-2-acetonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide at 60℃; for 1h;100%
heptanal
111-71-7

heptanal

sodium cyanide
143-33-9

sodium cyanide

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

Carbonic acid 1-cyano-heptyl ester ethyl ester

Carbonic acid 1-cyano-heptyl ester ethyl ester

Conditions
ConditionsYield
With tetrabutyl-ammonium chloride In dichloromethane; water Ambient temperature;100%
sodium cyanide
143-33-9

sodium cyanide

acetic anhydride
108-24-7

acetic anhydride

(R)-N-(isopropoxycarbonyl)phenylalaninal
129867-98-7

(R)-N-(isopropoxycarbonyl)phenylalaninal

(3-R)-2-acetoxy-3-isopropoxycarbonylamino-4-phenylbutyronitrile
129867-99-8, 129868-00-4

(3-R)-2-acetoxy-3-isopropoxycarbonylamino-4-phenylbutyronitrile

Conditions
ConditionsYield
With benzyltri(n-butyl)ammonium chloride In dichloromethane; water at 0℃; for 3h;100%
(2S)-3-(benzyloxy)-2-methylpropanal
79027-28-4

(2S)-3-(benzyloxy)-2-methylpropanal

sodium cyanide
143-33-9

sodium cyanide

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

(3R)-2-(4-methoxybenzylamino)-3-benzyloxymethylbutyronitrile
130533-04-9

(3R)-2-(4-methoxybenzylamino)-3-benzyloxymethylbutyronitrile

Conditions
ConditionsYield
With hydrogenchloride In methanol; water for 2h; Ambient temperature;100%
sodium cyanide
143-33-9

sodium cyanide

p-Toluenesulfonic acid 3-(indol-2-yl)propyl ester
107097-23-4

p-Toluenesulfonic acid 3-(indol-2-yl)propyl ester

4-(1H-Indol-2-yl)butanenitrile
165532-78-5

4-(1H-Indol-2-yl)butanenitrile

Conditions
ConditionsYield
In dimethyl sulfoxide Ambient temperature;100%
sodium cyanide
143-33-9

sodium cyanide

1-Benzenesulfonyl-2-(4-bromobutanyl)-1H-indole
165532-83-2

1-Benzenesulfonyl-2-(4-bromobutanyl)-1H-indole

5-(1-Benzenesulfonyl-1H-indol-2-yl)pentanenitrile
165532-84-3

5-(1-Benzenesulfonyl-1H-indol-2-yl)pentanenitrile

Conditions
ConditionsYield
In dimethyl sulfoxide at 80℃; for 12h;100%
sodium cyanide
143-33-9

sodium cyanide

2-[4-(3-Bromopropylcarbamoyl)-5-(trifluoromethyl)pyrazol-1-yl]-4-(3-trifluoromethylphenyl)thiazole
159886-35-8

2-[4-(3-Bromopropylcarbamoyl)-5-(trifluoromethyl)pyrazol-1-yl]-4-(3-trifluoromethylphenyl)thiazole

5-Trifluoromethyl-1-[4-(3-trifluoromethyl-phenyl)-thiazol-2-yl]-1H-pyrazole-4-carboxylic acid (3-cyano-propyl)-amide
1026655-81-1

5-Trifluoromethyl-1-[4-(3-trifluoromethyl-phenyl)-thiazol-2-yl]-1H-pyrazole-4-carboxylic acid (3-cyano-propyl)-amide

Conditions
ConditionsYield
In N,N-dimethyl-formamide100%

143-33-9Relevant articles and documents

Schuching,Enns

, p. 4255 (1956)

v.Hartel

, p. 189 (1934)

Physical Organic Studies on Bimolecular Reactions in Reversed Micelles: Addition of Cyanide Ion to the N-Methyl-3-carbamoylpyridinium Ion in Hexadecyltrimethylammonium Bromide Reversed Micelles

Goto, Ayako,Kishimoto, Hiroshi

, p. 73 - 78 (2007/10/02)

The bimolecular reaction of cyanide (CN-) ion with N-methyl-3-carbamoylpyridinium (S+) ion, in the water pool of the reversed-micellar system water/ hexadecyltrimethylammonium bromide (HTAB)/ chloroform-isooctane (3:2, v/v) has been studied at various temperatures (15-40 deg C) by measuring spectrophotometrically the decrease of the absorption due to S+ (265 nm) and the increase of the absorption due to the addition product (340 nm).The results of the reaction series were examined throughout with respect to the molar ratio of water to HTAB, R.Since the rate and equilibrium constants of the bimolecular reaction are affected by the method in which the concentrations of reactants are defined or by fixing the extent of reaction space, the water pool is assumed to be the sole reaction space and the rate and equilibrium constants in the water pool, k2w and Kw, which are based on the modified concentrations of the reaction species, have been evaluated.It is found that terms of k2w and Kw, the smaller the value of R, the more the addition reaction is enhanced.From the relationships between Kw and k2w vs. temperature, the standard and activation enthalpies of reaction, ΔH and ΔH, respectively, have been calculated.The behavior of ΔH and ΔH as well as Kw and k2w is found to differ in reactions which have R below and above ca.3.To explain the enhancement of the reaction due to the specific field effect of the water pool and the retardation of the reaction due to electrostatic interactions among S+ ions, the involvement of CN- and HTAB ions is proposed.The differing behaviour in the reactions is more clearly manifested in the thermodynamic and kinetic diagrams of enthalpy vs. entropy, which give separate plots corresponding to R both below and above ca.3.In addition, the effect of varying the CN- ion concentration is discussed and is found to be consistent with the situation described above.

Monooxygen Donation Potential of 4a-Hydroperoxyflavins As Compared with Those of a Percarboxylic Acid and Other Hydroperoxides. Monooxygen Donation to Olefin, Tertiary Amine, Alkyl Sulfide, and Iodide Ion

Bruice, Thomas C.,Noar, J. Barry,Ball, Sheldon S.,Venkataram, U. V.

, p. 2452 - 2463 (2007/10/02)

The reaction of the hydroxyperoxides diphenylhydroperoxyacetonitrile (4), methyl diphenylhydroperoxyacetate (5), and 5',6',7',8'-tetrahydro-4a'-hydroperoxy-3'-methylspiro-4'(3'H)-one (6) with I-, thioxane, and N,N-dimethylbenzylamine (DMBA) are first order in both hydroperoxide and substrate.For both 5 and 6, I3- is produced in 100percent yield.Product analysis for the reaction of 4, 5, and 6 with thioxane and DMBA established that the hydroxyperoxides are converted to the corresponding alcohols and that thioxane sulfoxide and N,N-dimethylbenzylamine N-oxide are formed.The reactions are quantitative.The reaction of 4 with I- proved to be complicated.The alcohol generated from 4 is the cyanohydrin of benzophenone.The dissociation of the benzophenone cyanohydrin product is competitive with I3- formation so that CN- produced in the dissociation reacts with I3- to yield ICN.Kinetic and thermodynamic analyses have provided the pertinent rate and equilibrium constants associated with the overall time course for reaction of 4 with I-.The second-order rate constant for the reaction of m-chloroperbenzoic acid (1) with I- has been determined and the second-order rate constant for reaction of 1 with thioxane was obtained from experiments in which thioxane and I- were employed as competitive substrates.The second-order rate constants for reaction of 1, 4, 5, and 6 with I-, thioxane, and DMBA were compared with like constants for the reactions of 4a-hydroperoxy-5-ethyl-3-methyllumiflavin (2), 1-carba-1-deaza-4a-hydroperoxy-5-ethyl-3-methyllumiflavin (3), t-BuOOH (7), and H2O2 (8).A log - log plot of the rate constants for monooxygen transfer from hydroperoxides to thioxane (kS) and to DMBA (kN) was found to be linear and of slope 1.0.The best line for the plot of log kS vs. the log of the rate constants for reactions with I- (kI) was of slope 1.1.The points for m-chloroperbenzoic acid were found to fit the log kS vs. log KI plot.These results show that the second-order rate constants for reactions of I-, thioxane, and DMBA are of like dependence on the electronic and steric characteristics of the hydroperoxides and percarboxylic acid 1.A linear free energy plot correlates the log of the second-order rate constants vs. pKa of YOH for oxygen transfer from YOOH = 1, 2, 4, 5, 7, and 8 (βlg = -0.6).In these reactions the 4a-hydroperoxyflavin 2 is the most efficient monooxygen donor of the hydroperoxides investigated, being 103 - 106 more reactive than t-BuOOH and ca. 103 less reactive than the peracid 1.The kinetics of epoxidation of 2,3-dimethyl-2-butene by the hydroperoxides 2 - 6 were invesigated by following both hydroperoxide disappearance and product formation.The results of these investigations, which include further reaction of epoxide with hydroperoxide to provide pinacol and 2,3-dimethyl-1-buten-3-ol, are discussed.Evidence for epoxidation of 2,3-dimethyl-2-butene ...

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