Cyanogen Chloride

HCID 10477CAS 506-77-4

Basic information

Standard SMILES
N#CCl
InChIKey
QPJDMGCKMHUXFD-UHFFFAOYSA-N
Molecular formula
CClN
Average molar mass
61.47 g/mol
Monoisotopic mass
60.97192668

Overview

Cyanogen chloride, stabilized appears as a chemical warfare blood agent. It is a colorless gas or liquid with a strong acrid/pungent odor. Shipped as a liquid confined under its own vapor pressure. A highly toxic lachrymator. Vapor is heavier than air. Prolonged exposure of the container to fire or intense heat may cause violent rupturing and rocketing.

Names & identifiers

Preferred name
Cyanogen Chloride
IUPAC
carbononitridic chloride
English name
Cyanogen chloride
Molecular formula
CClN
Molecular weight
61.47

Names & synonyms

CYANOGEN CHLORIDEChlorine cyanideChlorocyanideChlorocyanogenChlorcyancarbononitridic chlorideChlorocyan506-77-4Cyanogen chloride ((CN)Cl)Chlorine cyanide (ClCN)Chlorure de cyanogeneRCRA waste number P033
Show more names
Cyan chlorideChloro cyanideRCRA waste number P-033
697I61NSA0DTXSID4021551RefChem:580153DTXCID001551208-052-8ClCNCaswell No. 267Cyanic chloride

Database identifiers

CAS
506-77-4
PubChem CID
10477
DTXSID
DTXSID4021551
UNII
697I61NSA0
EC Number
208-052-8
Nikkaji
J2.609C

Properties

Computed structural properties

XLogP
1
Topological polar surface area
23.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
3

Experimental & physicochemical properties

Chemical Classes · 3 items

Toxic Gases & Vapors -> Cyanides

Reactive agents - 2nd degree

-> NIOSH Emergency Response Categories

SpringerMaterials PropertiesDunham energy parameter
PesticidesPesticide -> EPA IRIS
Odor · 3 items

Acrid, choking odor

Lachrimating and irritating odor

Strong acid/pungent odor

Density · 6 items

1.222 at 32 °F (USCG, 1999) - Denser than water; will sink

1.186 at 20 °C/4 °C

Density: 1.24 g/cu cm at 0 °C; 1.19 g/cu cm at 15 °C; Enthalpy of Fusion: 11.39 kJ/mol

Density/Specific gravity: 1.128 at 4 °C/4 °C

Liquid density 10.0 lb/gal. Shipped as a liquid confined under its own vapor pressure

1.22 (liquid at 32 °F)

Color/Form · 2 items

Colorless volatile liquid or gas

Colorless gas or liquid (below 55 °F) ...[NOTE: Shipped as a liquified gas. A solid below 20 °F.]

Physicochemical properties

Melting point
-6 ° · -6°
Boiling point
14 °C · 14°C
Density
1.186 · 1.186
vapor pressure
60 kPa · 60kPa at 0℃
solubility
2 O, · soluble in H2O, ethanol, ethyl ether
form
colorless gas

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H280 (65.1%): Contains gas under pressure; may explode if heated [Warning Gases under pressure]

P260, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P361+P364, P363, P391, P403+P233, P405, P410+P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 195 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H280: Contains gas under pressure; may explode if heated [Warning Gases under pressure]

Hazard information

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 4 items

Chemical: Cyanogen chloride ((CN)Cl)

Status: Active Update: 19-10-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/18184

Cyanogen chloride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety Information · 2 items

IMAP assessments - Cyanogen chloride ((CN)Cl): Environment tier I assessment

- Indoor Air: Cyanogen chloride (CK) can be released into indoor air as a liquid spray (aerosol) or as a gas.

DOT LabelPoison Gas Corrosive
Fire Hazards · 3 items

For information on chemical warfare blood agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

· Some may burn but none ignite readily.

Not combustible. Heating will cause rise in pressure with risk of bursting. Gives off irritating or toxic fumes (or gases) in a fire.

Fire Potential · 2 items

Not combustible. Heating will cause rise in pressure with risk of bursting. Gives off irritating or toxic gases including cyanide gas in a fire.

Not flammable.

Safety & protection

Fire Fighting · 3 items

For information on chemical warfare blood agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

In case of fire in the surroundings, use appropriate extinguishing media. In case of fire: keep cylinder cool by spraying with water. NO direct contact with water.

- Fire will produce irritating, corrosive, and/or toxic gases.

First Aid Measures · 3 items

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

ON FROSTBITE: rinse with plenty of water, do NOT remove clothes. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Do not touch or walk through spilled material.

First Aid · 3 items

For information on chemical warfare blood agents see the ERG Criminal or Terrorist Use of CBR Agents. (ERG, 2024)

General First Aid:

(General first aid procedures)

Safe StorageFireproof if in building. Provision to contain effluent from fire extinguishing. Cool. Store in an area without drain or sewer access.
Firefighting HazardsIt may only be shipped in cylinders. Prolonged exposure of the cylinder to fire or heat may cause violent rupturing and rocketing. /Cyanogen chloride, inhibited/

Toxicology

Treatment · 1 item

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

Target Organs · 2 items

Endocrine

Eyes, skin, respiratory system, central nervous system, cardiovascular system

Health Effects · 1 item

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Ecotoxicity Values · 4 items

LC50; Species: Daphnia magna (Water flea) age 24 hr; Conditions: static bioassay; Concentration: 0.04 mg/L for 24 hr

LC50; Species: Daphnia magna (Water flea) age 24 hr; Conditions: static bioassay; Concentration: 0.029 mg/L for 48 hr

LC50; Species: Daphnia magna (Water flea) age 5 day; Conditions: static bioassay; Concentration: 0.086 mg/L for 24 hr

LC50; Species: Daphnia magna (Water flea) age 5 day; Conditions: static bioassay; Concentration: 0.065 mg/L for 48 hr

Environmental Fate · 4 items

The environmental fate of cyanogen chloride is largely site specific in that the biotic and abiotic characteristics of soil and water greatly influence the ability of this compound to persist, absorb, degrade, dissociate, and complex(1). However, because of its volatility and rapid rate of hydrolysis, cyanogen chloride is considered a nonpersistent agent(2,3).

TERRESTRIAL FATE: Data on cyanogen chloride fate in soil were not available; however, it is highly volatile and hydrolyzes rapidly in the environment(1).

AQUATIC FATE: Cyanogen chloride is extremely volatile from water surfaces and will hydrolyze rapidly(1) with half-lives ranging from 1 minute 45 seconds to 10 hours at 5 °C in ambient waters(2).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyanogen chloride, which has a vapor pressure of 1.22X10+3 mm Hg at 25 °C(2), is expected to exist solely as a gas in the ambient atmosphere. Cyanogen chloride does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOther Poison - Chemical Asphyxiant

Regulatory information

RCRA Requirements · 2 items

P033; As stipulated in 40 CFR 261.33, when cyanogen chloride, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

D003; A solid waste containing cyanogen chloride may or may not become characterized as a hazardous waste when subjected to the Toxicity Characteristic Leaching Procedure listed in 40 CFR 261.24, and if so characterized, must be managed as a hazardous waste.

Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Cyanogen chloride is produced, as an intermediate or final product, by process units covered under this subpart.

CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act Requirements · 4 items

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Cyanides/

Cyanogen chloride is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

The procedures described in the "Guidelines for Deriving Numerical National Water Quality Criteria for the Protection of Aquatic Organisms and Their Uses" indicate that, except possibly where a locally important species is very sensitive, freshwater aquatic organisms and their uses should not be affected unacceptably if the four day average concentration of cyanide does not exceed 5.2 ug/l more than once every three years on the average and if the one hour average concentration does not exceed 22 ug/l more than once every three years on the average. /Cyanide/

The procedures described in the "Guidelines for Deriving Numerical National Water Quality Criteria for the Protection of Aquatic Organisms and Their Uses" indicate that, except possibly where a locally important species is very sensitive, saltwater aquatic organisms and their uses should not be affected unacceptably if the one hour average concentration of cyanide does not exceed 1.0 ug/l more than once every three years on the average. /Cyanide/

DHS Chemicals of Interest (COI) · 6 items

Cyanogen chloride

1

10000

2.67

15

Toxic chemical that can be released at a facility.

State Drinking Water GuidelinesFl) Florida 350 ug/L

Safety data

OEL
Ceiling: 0.3 ppm (0.6 mg/m3)
tsca
TSCA listed
ridadr
UN 1589 (CYANOGEN CHLORIDE, STABILIZED)
Toxicity
CK may polymerize violently if contaminated with hydrogen chloride or ammonium chloride. Upon heating, it decomposes, producing toxic and corrosive fumes of hydrogen cyanide, hydrochloric acid, and nitrogen oxides. Hazardous polymerization can occur. Cyanogen chloride will react slowly with water to form hydrogen chloride gas. It acts on the body in two ways. Systemic effects of CK are much like those of hydrogen cyanide. Additionally, it causes irritation of the eyes, upper respiratory tract, and lungs. Eye irritation results in tearing. CK, like AC, stimulates the respiratory system and rapidly paralyzes it. Exposure is followed by immediate, intense irritation of the nose, throat, and eyes, with coughing, tightness in the chest, and lacrimation. This is followed by dizziness and increasing difficulty breathing. Unconsciousness comes next, with failing respiration and death within a few minutes. Convulsions, retching, and involuntary urination and defecation may occur. If these effects are not fatal, the signs and symptoms of pulmonary edema may develop. There may be repeated coughing, with profuse foamy sputum, rales in the chest, severe dyspnea, and distinct cyanosis. Recovery from the systemic effects is usually as prompt as in AC poisoning. However, a higher incidence of residual damage to the central nervous system should be expected. Based upon the concentration of the cyanogen chloride to which the victim has been exposed, the pulmonary effects may evolve instantly or may be delayed until the systemic effects have subsided. Consequently, early prognosis must be cautious.
Signal word
Danger
Symbol(GHS)
GHS09,GHS05,GHS04,GHS06

Chemistry & industry

Pharmacology

Biological Half-LifeThe blood elimination half-life of cyanide varies widely, from a few minutes to up to 66 hours, depending on many factors...
Metabolism/Metabolites · 6 items

Cyanogen chloride is apparently converted to cyanide ion in vivo by a reaction with hemoglobin and glutathione, which eventually liberates the CN ion.

Forms cyanide in the body

The small quantity of cyanide always present in human tissues is metabolized at the approximate rate of 17 ug/kg x min, primarily by the hepatic enzyme rhodanese, which catalyzes the irreversible reaction of cyanide and a sulfane to produce thiocyanate, a relatively nontoxic compound excreted in the urine. ... The limiting factor under normal conditions is the availability of a sulfane as a substrate for rhodanese, and sulfur is administered therapeutically as sodium thiosulfate to accelerate this reaction. The lethal dose of cyanide is time dependent because of the ability of the body to detoxify small amounts of cyanide via the rhodanese-catalyzed reaction with sulfane. A given amount of cyanide absorbed slowly may cause no biological effects even though the same amount administered over a very short period of time may be lethal. /Hydrogen cyanide and cyanogen chloride/

Cyanogen chloride is apparently converted to cyanide ion in vivo by a reaction with hemoglobin and glutathione, which eventually liberates the CN ion.

Cyanogen chloride reacts rapidly with both serum and red cells, but cyanide is produced only from ther reaction with red cells. As would be expected...., higher percentage conversions of cyanogen chloride to cyanide are obtained with washed red cells than with whole blood. ... Cyanogen chloride reacts rapidly with rat hemoglobin, no more than 1% of the original cyanogen chloride added being left after 5 sec from a mixture of cyanogen chloride (17.3 ug/mL) and of hemoglobin (5-7 vol O2%). ... It would appear that the essential reactions in the production of of cyanide from cyanogen chloride and blood are an initial reaction with hemoglobin followed by liberation of cyanide by reaction with glutathione. However, cyanogen chloride reacts directly with glutathione. The rate of reaction is of the same order as with hemoglobin. ... Since the rate of reaction of cyanogen chloride with hemoglobin and with glutathione is of the same order, it is possible that both reactions contribute to the conversion of cyanogen chloride to cyanide in vivo.

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

Absorption, Distribution and Excretion · 1 item

Much of total body burden appears to reside in the erythrocyte, bound to endogenous methemoglobin and, to a lesser extent, normal hemoglobin. However, cyanide is detectable in virtually every organafter significant exposures, particularly those organs with high blood flow.

Uses & manufacturing

Uses · 6 items

Used in organic synthesis, a warning gas in fumigants, and as a military poison gas; May be generated in a reaction of hypochlorite and cyanide solutions in waste water treatment; [ACGIH] Used in metal cleaning and ore refining; [ATSDR ToxProfiles]

Acid and Alkali Cleaning of Metals [Category: Clean]

For cyanogen chloride (USEPA/OPP Pesticide Code: 025801) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Used for the commercial production of cyanuric chloride, a starting material for pesticides, dyes, and drugs

Chemical synthesis; military poison gas

Warning agent in fumigant gases

U.S. ProductionWorldwide production capacity is more than 230,000 tons/ annually (mainly in Europe and the United States)
Methods of Manufacturing · 3 items

/It is prepared/ by action of chlorine on hydrogen cyanide.

Cyanogen chloride is produced by action of chlorine on moist sodium cyanide suspended in carbon tetrachloride and kept cooled to -3 °C, followed by distillation.

The preparation of the industrially important ClCN has been developed extensively; the synthetic pathways are as follows: 1) Electrolysis of an aqueous solution of HCN and NH4Cl. 2) Reaction of complex cyanide salts (e.g., Na2(Zn(CN)4)) with chlorine below 20 °C. 3) Formation of ClCN from cyanide salts (mostly NaCN) and chlorine in an exothermic reaction; in a continuous process, sprayed aqueous NaCN solution is contacted with chlorine, and the reaction heat evaporates the ClCN. 4) Processes involving hydrogen cyanide and chlorine as the most convenient starting materials; the reaction is carried out in aqueous solution ... in organic and inorganic solvents, and in the gas phase. To avoid the byproduct HCl, attempts have been made to reoxidize HCl to chlorine with oxygen and hydrogen peroxide in catalyzed reactions. 5) Chlorinolysis of cyanogen in the gas phase at 300-600 °C in the presence of a catalyst. 6) Pyrolysis of cyanuric chloride at 600-900 °C in the presence of a charcoal catalyst. and 7) High-temperature syntheses based on elemental chlorine, nitrogen, and carbon. Usually, these processes lead to impure ClCN; therefore, in many cases the product must be purified before further use.

General Manufacturing Information · 5 items

Cyanogen chloride ((CN)Cl): ACTIVE

/The Chemical Weapons Convention (CWC) is an international treaty which bans the development, production, stockpiling, and transfer or use of chemical weapons. The Convention mandates the destruction and prohibition of chemical weapons and related facilities and provides for restrictions on international trade in toxic chemicals and precursors./ The Convention's monitoring and verification measures involve submission of declarations regarding ... /Schedule 1, 2, and 3 chemicals/ and inspections by the Organization for the Prohibition of Chemical Weapons of the facilities where these chemicals are produced. ... Schedule 3 chemicals ... /may/ have been stockpiled or used as weapons, but ... are produced /and used/ in large quantities for purposes not prohibited by the Convention (2). Cyanogen chloride is listed in the CWC Annex on Chemicals under Schedule 3 (1).

Cyanogen chloride is an intermediate in the detoxification of cyanide-containing wastewater with sodium hypochlorite solutions; therefore, the cyanogen halide must be removed immediately by appropriate hydrolysis.

Cyanogen chloride has been identified as a by-product of aqueous chlorination of purines and pyrimidines as a result of chlorination of potable water and wastewater.

One of the many dual-use compounds thought to be located at one or more nonstockpile locations in the continental US

Applications · 6 items

DescriptionCyanide poisoning was first reported with the effects of extract of bitter almonds; then cyanide was identified and isolated from cherry laurel. Cyanogen chloride was first prepared in 1787 by the action of chlorine upon hydrocyanic acid (aka prussic acid) and was called ‘oxidized prussic acid.’ The correct formula for cyanogen chloride was first established in 1815. Cyanogen chloride was used in World War I in 1916.

HistoryCyanogen chloride (CK) is a very volatile compound, but is less a fire or explosive hazard than hydrogen cyanide and therefore logistically speaking less problematic. (Industry has found cyanogen chloride the preferred reactant in processes to make synthetic rubber). Reportedly, France combined hydrocyanic acid with cyanogen chloride in World War I ("manguinite"). The use of cyanogen chloride in this mixture was intended as an irritant to make soldiers remove their masks, exposing themselves to these very toxic gases. Cyanogen chloride was also combined with arsenic trichloride later on in the war. Like hydrocyanic acid, cyanogen chloride tends to spontaneously polymerize and therefore was combined with stabilizers (sodium pyrophosphate) for longer shelf life.

UsesCyanogen chloride is used in organic synthesis and as a military poisonous gas. Several benzene derivatives react with chloramine or with hypochlorous acid in the presence of ammonium ion to form cyanogen chloride (Maeda et al. 1987).

UsesIn chemical synthesis. Military poison gas.

UsesOrganic synthesis; poison gas used by military

General DescriptionA colorless gas or liquid with a strong acrid/pungent odor. Boils at 60°F. Liquid density 10.0 lb / gal. Shipped as a liquid confined under its own vapor pressure. A highly toxic lachrymator. Has been used as a tear gas. Vapor is heavier than air. Prolonged exposure of the container to fire or intense heat may cause violent rupturing and rocketing.

Related reactions

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