460-19-5

Basic information

• Product Name: CYANOGEN
• Synonyms: OXALONITRILE;CYANOGEN;dicyan;cyanogene;dicyanogene;oxalonitrile cyanogen;Carbon nitride (C2N2);Cyanogen (C2N2)
• CAS NO: 460-19-5
• Molecular Formula: C₂N₂
• Molecular Weight: 26.0174
• EINECS: 207-306-5
• Product Categories: Organics
• Mol File: 460-19-5.mol
• Article Data: 55

Chemical Properties

• Melting Point: -27.9° (also reported as -34.4°)
• Boiling Point: bp -21.17°
• Flash Point: °C
• Appearance: /colorless gas
• Density: d4-21.17 0.9537
• Vapor Pressure: 4310mmHg at 25°C
• Refractive Index: 1.3780 (estimate)
• Water Solubility: 1.51E+05 mg/L at 25℃
• CAS DataBase Reference: CYANOGEN(CAS DataBase Reference)
• NIST Chemistry Reference: CYANOGEN(460-19-5)
• EPA Substance Registry System: CYANOGEN(460-19-5)

Safety Data

• Hazard Codes: F,T,N
• Statements: 11-23-50/53
• Safety Statements: 23-45-60-61
• RIDADR: 1026
• HazardClass: 2.3
• Hazardous Substances Data: 460-19-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 460-19-5 differently. You can refer to the following data:
1. Cyanogen has limited applications, the most important of which are in organic synthesis. Also, it is used in welding metals; as a fumigant; and in some rocket propellants.
2. Cyanogen is used as a fumigant, as a fuel gas for welding and cutting metals, as a propellant, and in organic synthesis. It occurs in blast-furnace gases. It is also known to occur at varying concentrations in cassava flour consumed in northern Mozambique.
3. Organic synthesis; fuel gas for welding and cutting heat-resistant metals; rocket and missile propellant; fumigant

Preparation

Cyanogen is prepared by the slow addition of potassium cyanide solution to a solution of copper(II) salt, such as copper(II) sulfate or chloride: 2Cu2+ + 4CNˉ → 2CuCN + (CN)2 Cyanogen also may be prepared by the reaction of mercuric cyanide with mercuric chloride. Dry cyanogen gas may be obtained by this process: Hg(CN)2 + HgCl2 → Hg2Cl2 + (CN)2 yanogen may be prepared by oxidation of hydrogen cyanide with oxygen, nitrogen dioxide, chlorine, or another suitable oxidizing agent, using various catalysts: 4HCN + O2 → 2(CN)2 + H2O 2HCN + NO2 →(CN)2 + NO + H2O 2HCN + Cl2 →(CN)2 + 2HCl

Hazard

Cyanogen is a highly flammable gas. It forms explosive mixtures with air, LEL 6.6%, UEL 32% by volume. Reactions with oxygen, ozone, fluorine or other strong oxidizing agents can be explosive. Also, it can explode when exposed to spark, flame or heat. Cyanogen is moderately toxic by inhalation. Exposure causes irritation of the eyes, nose and respiratory tract. A 10-minute exposure to about 10 ppm of the gas can manifest these irritant action in humans. LC50 (rat): 350 ppm in 1 hour.

Chemical Properties

Cyanogen is a colorless, flammable, com- pressed liquefied gas at room temperature. At deadly levels only, it has a pungent, almond-like odor.

Production Methods

Different sources of media describe the Production Methods of 460-19-5 differently. You can refer to the following data:
1. Cyanogen is prepared (1) by reaction of sodium cyanide and copper sulfate solutions, whereby one half the cyanogen is evolved as cyanogen gas and one half remains as cuprous cyanide. From the filtered cuprous cyanide, by treatment with ferric chloride solution, cyanogen is evolved with accompanying formation of ferrous chloride, (2) by heating ammonium oxalate COONH4·COONH4 with phosphorus pentoxide, water being abstracted. Small amounts of cyanogen are present in blast furnace gas and raw coal gas.
2. Cyanogen can be prepared by slowly dropping potassium cyanide solution into copper sulfate solution or by heating mercury cyanide.

Definition

Different sources of media describe the Definition of 460-19-5 differently. You can refer to the following data:
1. A toxic flammable gas prepared by heating mercury cyanide.
2. cyanogen: A colourless gas, (CN)2,with a pungent odour; soluble inwater, ethanol, and ether; d. 2.335g dm–3; m.p. –27.9°C; b.p. –20.7°C.The compound is very toxic. It maybe prepared in the laboratory byheating mercury(II) cyanide; industriallyit is made by gas-phase oxidationof hydrogen cyanide using air over asilver catalyst, chlorine over activatedsilicon(IV) oxide, or nitrogendioxide over a copper(II) salt.Cyanogen is an important intermediatein the preparation of various fertilizersand is also used as a stabilizerin making nitrocellulose. It is an exampleof a pseudohalogen.
3. ChEBI: A dinitrile that is ethane substituted by two cyano groups.

Reactions

Cyanogen (CN)2 is a colorless gas of marked characteristic odor, very poisonous, density 1.8 (air equal to 1.0), soluble. When passed into water at 0 °C, cyanogen forms hydrocyanic acid plus cyanic acid, but at ordinary temperatures the reaction is complex. With sodium hydroxide solution, there is formed with cyanogen sodium cyanide plus sodium cyanate, with dilute sulfuric acid oxamic acid COOH·CONH2, oxalic acid COOH·COOH. By reaction with tin and hydrochloric acid, cyanogen is reduced to ethylene diamine CH2·NH2·CH2·NH2. Cyanogen reacts with hydrogen to form hydrocyanic acid, and with metals, e.g., zinc, copper, lead, mercury, silver, to form cyanides.Cyanogen, (1) when burned in air produces a violet flame forming carbon dioxide and nitrogen in the outer part and carbon monoxide and nitrogen in the inner part, (2) when exploded with oxygen produces carbon dioxide or carbon monoxide and nitrogen depending upon the ratio of oxygen to cyanogen (2 volumes oxygen plus 1 volume cyanogen yields 2 volumes carbon dioxide plus 1 volume nitrogen; 1 volume oxygen plus 1 volume cyanogen yields 2 volumes carbon monoxide plus 1 volume nitrogen). The flame spectrum contains characteristic bands in the blue and violet. By means of the electric spark, the electric arc or a red hot tube, cyanogen is decomposed into carbon plus nitrogen. When heated at ordinary pressure at about 300 °C, or under 300 atmospheres pressure at about 225°, cyanogen is converted into paracyanogen, a brown powder, also formed when mercuric cyanide is heated.

General Description

A colorless gas with an odor of almonds. Freezes at -28°C and boils at -20.7°C. Shipped as a liquid confined under its vapor pressure. The gas is heavier than air and a flame can travel back to the source of leak very easily. Prolonged exposure to fire or intense heat may cause the containers to violently rupture and rocket. Used to make other chemicals, as a fumigant, and as a rocket propellant.

Air & Water Reactions

Highly flammable. Soluble in water and slowly decomposed by water to oxalic acid and ammonia.

Reactivity Profile

Colorless, flammable, highly toxic gas. CYANOGEN can react explosively with strong oxidants (dichlorine oxide, fluorene, oxygen, ozone). When heated to decomposition or on contact with acids, acid fumes, water or steam CYANOGEN will react to produce deadly hydrogen cyanide gas and oxides of nitrogen [Sax, 9th ed., 1996, p. 945].

Health Hazard

Different sources of media describe the Health Hazard of 460-19-5 differently. You can refer to the following data:
1. Vapor irritates eyes and causes giddiness, headache, fatigue, and nausea if inhaled.
2. Cyanogen is a highly poisonous gas having toxic symptoms similar to those of HCN. Acute exposure can result in death by asphyxia. The toxic routes are inhalation and percutaneous absorption. At sublethal concentrations the symptoms of acute toxicity are nausea, vomiting, headache, confusion, and weakness. Rats exposed to cyanogen exhibited toxic symptoms of respiratory obstruction, lacrimation, and somnolence. Exposure to 350 ppm for 1 hour caused death to 50% of test animals. In humans, exposure to 16 ppm for 5 minutes produced irritation of eyes and nose. Toxicity of cyanogen is considerably lower than that of HCN. Lethal dose in test animals from subcutaneous injection varied between 10 and 15 mg/kg. Ernesto et al. (2002) have reported persistent konzo epidemics and subclinical upper motor neuron damage along with an elevated urinary thiocyanate concentration in school children in Mozambique who were exposed to high cyanogen concentrations from cassava flour. A subchronic toxicity study conducted on male rhesus monkeys and male albino rats exposed over a period of 6 months (6 hours/day, 5 days/week) indicated marginal toxicity of cyanogen at 25 ppm (Lewis et al. 1984). Total lung moisture content and body weights were significantly lower. The odor threshold level for cyanogen is about 250 ppm.

Fire Hazard

Highly flammable, burns with a purpletinged flame; vapor density 1.8 (air = 1); the vapor may travel a considerable distance to an ignition source and flash back; fireextinguishing procedure: use a water spray to fight fire and keep fire-exposed containers cool; shut off the flow of gas. Cyanogen forms an explosive mixture with air within the range of 6.6–32%. Liquid cyanogen can explode when mixed with liquid oxygen. When mixed with an acid or water or when heated to decomposition, it produces toxic fumes.

Safety Profile

: A poison by subcutaneous and possibly other routes. Moderately toxic by inhalation. Human systemic effects by inhalation: damage to the olfactory nerves and irritation of the conjunctiva. A systemic irritant by inhalation and subcutaneous routes. A human eyeirritant. Very dangerous fire hazard when exposed to heat, flames (sparks), or oxidizers. To fight fire, stop flow of gas. Potentially explosive reaction with powerful oxidants (e.g., dichlorine oxide, fluorine, oxygen, ozone). When heated to decomposition or on contact with acid, acid fumes, water, or steam will react to produce highly toxic fumes of NOx and CN-. See also other cyanogen entries and CYANIDE.

Potential Exposure

Cyanogen is currently used as an intermediate in organic syntheses; at one time, it was used in poison gas warfare.

storage

Cyanogen is stored outside or in a detached area: cool, dry, and well ventilated, and isolated from acid, acid fumes, and water. It is shipped in high-pressure metal cylinders of.

Shipping

UN1026 Cyanogen, Hazard Class: 2.3; Labels: 2.3-Poisonous gas, 2.1-Flammable gas, Inhalation Hazard Zone B. Cylinders must be transported in a secure upright position, in a well-ventilated truck. Protect cylinder and labels from physical damage. The owner of the compressed gas cylinder is the only entity allowed by federal law (49CFR) to transport and refill them. It is a violation of transportation regulations to refill compressed gas cylinders without the express written permission of the owner.

Incompatibilities

Chemically unstable in rising tempera- tures. May form explosive mixture with air. Explosive reac- tion with strong oxidizers (e.g., dichlorine oxide, fluorine). Forms toxic gases on contact with acids, including hydro- gen cyanide. Slowly hydrolyzed in water to form hydrogen cyanide, oxalic acid, and ammonia.

Waste Disposal

Return refillable compressed gas cylinders to supplier. Incineration; oxides, or nitrogen are removed from the effluent gas by scrubbers and/or ther- mal devices.

InChI:InChI=1/C2N2/c3-1-2-4

Upstream product

• 143-33-9 sodium cyanide 
• 333-20-0 potassium thioacyanate 
• 1113-38-8 ammonium oxalate 
• 74-86-2 acetylene 
• 460-12-8 Butadiyne 
• 460-19-5 cyanogen cation 
• 75-05-8 acetonitrile 
• 114698-73-6 3-phenyl-1-(1H-tetrazol-5-yl)-tetraz-1-ene 
• 539-57-1 4-(1⁽²⁾H-tetrazol-5-yl)-tetraz-3-ene-1-carboximidic acid amide 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 74-89-5 methylamine 
• 79-40-3 dithiooxamide 
• 56-23-5 tetrachloromethane 

Downstream Products

• 1003-31-2 thiophene-2-carbonitrile 
• 75-05-8 acetonitrile 
• 74-90-8 hydrogen cyanide 
• 13534-15-1 diethyl oximidate 
• 95-92-1 oxalic acid diethyl ester 
• 157368-88-2 1,2-Bisethan-1,2-diamin 
• 471-46-5 Oxalamide 
• 6640-47-7 2,3-diaminoquinoxaline 
• 412308-12-4 2,3-diamino-1-methyl-quinoxalinium-betaine 
• 89809-64-3 2-cyano-5-chloropyridine 
• 19235-89-3 4-chloro-pyridine-2-carbonitrile 
• 100621-07-6 oxalomonoimidic acid-(4'-amino-biphenyl-4-ylamide)-nitrile 
• 120639-55-6 N,N''-bis-(4'-amino-biphenyl-4-yl)-oxalamidine 
• 1620-76-4 2-Cyano-4-methylpyridin 

Relevant articles and documents

Laser measurements of the effects of vibrational energy on the reactions of CN

Pulsed laser photolysis of C2N2 at 193 nm has been used as a source of CN radicals in both the ν = 0 and ν =1 levels.Individual rovibronic levels of these radicals were measured as a function of time with a tunable dye laser.From these measurements the rate constants for the reaction of each of these vibrational levels with Hz, O2, CO, CO2, N2, HCN, C2N2, and CH4 have been determined.Some enhancement in the rate constant with vibrational energy which could not be ascribed to quenching was observed for O2, CH4, and H2.Only vibrational quenching was observed for HCN, N2, CO2, CO, and C2N2.In the CO case the vibrational quenching rate appears to be significantly enhanced by complex formation during the quenching process.

Studies of the Anodic Oxidation of the Cyanide Ion in the Presence of the Copper Ion. IV. The Kinetics and Mechanism of the Decomposition of the Intermediate Tetracyanocuprate(II) Ion

The kinetics and mechanism of the decomposition of the tetracyanocuprate(II) ion (CuII(CN)42-) have been investigated by ESR measurements.Aqueous solutions of potassium cyanide with a small amount of copper(I) cyanide were electrolyzed in a cell the platinum anode of which was set in the resonant cavity of an ESR spectrometer.Since CuII(CN)42-, which is formed as an intermediate, gives a definite ESR spectrum, its concentration in the anode compartment is estimated from the intensity of the first-derivative spectrum at a fixed magnetic field.From the decay curves of the ESR intensity after the steady-state electrolysis currents have been switched off, a rate equation for the decomposition of CuII(CN)42- is derived; v = k0II(CN)42->2/->2, where k0 is calculated to be 74 mol*dm-3*s-1 at 25 deg C.This rate equation is also confirmed by ESR measurements during steady-state electrolysis, where the value of k0 = 60 mol*dm-3*s-1 is obtained.On the basis of the kinetics, two possible mechanisms are proposed: the formation of CuII(CN)3-, followed by the rate-determining bimolecular reaction of CuII(CN)3- to give 2CuI(CN)2- + (CN)2 (Mechanism A), and the formation of a binuclear complex, CuII2(CN)62-, followed by the rate-determining decomposition of CuII2(CN)62- to give 2CuI(CN)2- + (CN)2 (Mechanism B).The kinetics and the mechanism are compared with those of the chemical reaction between the copper(II) ion and the cyanide ion.

1H, 13C NMR and UV spectroscopy studies of gold(III)-tetracyanide complex with l-cysteine, glutathione, captopril, l-methionine and dl-seleno-methionine in aqueous solution

Auricyanide [Au(CN)4]- interaction with biologically important thiols, thioether and selenoether were carried out and monitored using 1H, 13C NMR and UV spectroscopy. These ligands include l-cysteine, glutathion

Synthesis and crystal structures of novel tertiary butyl substituted (pseudo-)halogen bismuthanes

Herein we present the synthesis and characterization of di-tertiary butyl substituted (pseudo-)halogen bismuthanes tBu2BiX (X = Cl (1), Br (2), I (3), CN (4), N3 (5), SCN (6)). These compounds were obtained via different reaction paths. Compound 1 was obtained by a Grignard reaction of BiCl3 with two equivalents of tBuMgCl, whereas compounds 2, 3, 4 and 6 were synthesised by a oxidative addition/reductive elimination pathway starting from tBu3Bi and X2 (X = Br, I, CN, SCN). Finally, azide 5 was obtained by the reaction of 1 and NaN3. Secondary bonding interactions in the solid state within all the investigated compounds (1-6) cause additional stabilisation. Starting from tBu2BiCl, the completely tbutyl substituted ternary interpnictogen compound tBu2Bi(tBuP)SbtBu2 (7) was synthesized through the reaction with [tBu2SbP(tBu)Li(Et2O)]2. All new compounds were characterized by means of X-ray diffraction and mass spectrometry as well as NMR and IR spectroscopy.

An exploding: N -isocyanide reagent formally composed of anthracene, dinitrogen and a carbon atom

Targeted as an example of a compound composed of a carbon atom together with two stable neutral leaving groups, 7-isocyano-7-azadibenzonorbornadiene, CN2A (1, A = C14H10 or anthracene) has been synthesized and spectroscopically and structurally characterized. The terminal C atom of 1 can be transferred: mesityl nitrile oxide reacts with 1 to produce carbon monoxide, likely via intermediacy of the N-isocyanate OCN2A. Reaction of 1 with [RuCl2(CO)(PCy3)2] leads to [RuCl2(CO)(1)(PCy3)2] which decomposes unselectively: in the product mixture, the carbide complex [RuCl2(C)(PCy3)2] was detected. Upon heating in the solid state or in solution, 1 decomposes to A, N2 and cyanogen (C2N2) as substantiated using molecular beam mass spectrometry, IR and NMR spectroscopy techniques.