Sodium Cyanide

Base Information

• Chemical Name: Sodium Cyanide
• CAS No.: 143-33-9
• Deprecated CAS: 13998-03-3,25596-52-5
• Molecular Formula: NaCN
• Molecular Weight: 49.0075
• Hs Code.: 28371110
• European Community (EC) Number: 205-599-4
• ICSC Number: 1118
• NSC Number: 77379
• UN Number: 1689,1935,3414
• UNII: O5DDB9Z95G
• DSSTox Substance ID: DTXSID4024309
• Wikipedia: Sodium cyanide,Sodium_cyanide
• Wikidata: Q410185
• NCI Thesaurus Code: C163699
• Pharos Ligand ID: ZYG7HNTATU9K
• ChEMBL ID: CHEMBL1644697
• Mol file: 143-33-9.mol

Synonyms:Cyanide, Sodium;Cyanogran;Sodium Cyanide

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Chemical Property of Sodium Cyanide

Chemical Property:

• Appearance/Colour: white crystals
• Vapor Pressure: 1 mm Hg ( 817 °C)
• Melting Point: 563.7 °C
• Boiling Point: 1497 °C
• PKA: 9.36[at 20 ℃]
• Flash Point: 1500°C
• PSA: 23.79000
• Density: 1.6 g/cm³
• LogP: 0.01678
• Storage Temp.: Poison room
• Sensitive.: Hygroscopic
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: 37 g/100mL (20 ºC)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 48.99284329
• Heavy Atom Count: 3
• Complexity: 12.8
• Transport DOT Label: Poison

Purity/Quality:

Safty Information:

• Pictogram(s): T+,N
• Hazard Codes: T+,N
• Statements: 26/27/28-32-50/53-48/25
• Safety Statements: 7-28-29-45-60-61-28A

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Cyanides
• Canonical SMILES: [C-]#N.[Na+]
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes, skin and respiratory tract. The substance may cause effects on the cellular respiration. This may result in convulsions and unconsciousness. Exposure could cause death. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the thyroid.
• Uses: 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. 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. Extracting gold and silver from ores; electroplating baths; case hardening steel by liquid nitriding; manufacture of hydrocyanic acid and other cyanides. 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.
• 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.

Technology Process of Sodium Cyanide

There total 91 articles about Sodium Cyanide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

ethanol (64-17-5) + benzonitrile (100-47-0) + toluene (108-88-3,15644-74-3,16713-13-6) → sodium cyanide (143-33-9,25596-52-5) + benzylamine (100-46-9)

Guidance literature:

Siedetemperatur;

DOI:10.1021/ja01322a051

Reference yield:

ethanol (64-17-5) + benzonitrile (100-47-0) → sodium cyanide (143-33-9,25596-52-5) + benzoic acid (65-85-0,8013-63-6) + benzylamine (100-46-9) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

Reference yield:

4-cyano-1,4-dihydro-N-methylpyridine-3-carboxamide (19432-60-1) → sodium cyanide (143-33-9,25596-52-5) + 1-methylnicotinamide chloride (1005-24-9)

Guidance literature:

at 25 ℃; Equilibrium constant; reaction in reversed-micellar system H₂O/ HTAB/ CHCl₃-isooctane, diff. molar ratios H₂O/ HTAB, other temp.;

DOI:10.1039/P29900000073

upstream raw materials:

methanol

benzo[d]thiazol-2-yl thiocyanate

diethyl ether

bromocyane

Downstream raw materials:

PCN

benzoic acid ethyl ester

benzaldehyde

3,3-bis-cyanomethyl-oxetane

Refernces

Improved three-component lewis acid-free approach for the synthesis of protected racemic cyanohydrins

10.1080/00304940809458105

The research focuses on an improved, Lewis acid-free approach for the synthesis of protected racemic cyanohydrins, which are valuable in pharmaceuticals and agrochemicals. The study utilizes a three-component reaction involving benzaldehyde, sodium cyanide, and acetic anhydride in an eco-friendly solvent, PEG-400, at room temperature. This method yields protected racemic cyanohydrins with moderate to excellent results, comparable to Lewis acid-catalyzed reactions. The experiments conducted encompass a series of sterically and electronically differentiated aromatic substrates, as well as aliphatic and heteroaromatic aldehydes, to define the scope of the synthesis. The analyses used to characterize the products include 'H NMR, 13C NMR, IR spectroscopy, mass spectrometry, and elemental analysis, providing comprehensive data on the structure and composition of the synthesized cyanohydrins.

A practical synthesis of (+)-biotin from L-cysteine

10.1002/chem.200400733

The research focuses on the practical synthesis of (+)-biotin from l-cysteine, a significant endeavor due to biotin's crucial role in human nutrition and animal health. The study aims to address the inefficiencies of the existing Goldberg and Sternbach method, which involves over 14 steps, utilizes toxic reagents, and requires impractical diastereomeric or enzymatic resolution. The researchers developed a novel synthetic approach that eliminates the need for bulky protecting groups and reduces the protection-deprotection sequence steps. This method involves the formation of contiguous stereogenic centers through a highly diastereoselective Strecker reaction, a novel ring transformation and deblocking by S,N-carbonyl migration, and the introduction of the carbon chain at C-4 by the Fukuyama coupling reaction. Key chemicals used in the process include l-cysteine, phenyl chloroformate, benzyl bromide, benzyl chloride, sodium bisulfite, sodium cyanide, and various catalysts and reagents for the reactions involved. The conclusions of the research highlight the successful development of a more efficient synthetic method for (+)-biotin, achieved in 10 steps and with an overall yield of 34% from l-cysteine, offering a high yield, ease of operation, and mild reaction conditions.