Cyanogen chloride

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Cyanogen chloride
Cyanogen-chloride.svg
Ball and stick model of cyanogen chloride Cyanogen-chloride-3D-balls.png
Ball and stick model of cyanogen chloride
Spacefill model of cyanogen chloride Cyanogen-chloride-3D-vdW.png
Spacefill model of cyanogen chloride
Names
Preferred IUPAC name
Carbononitridic chloride
Systematic IUPAC name
Chloroformonitrile
Other names
  • Chlorine cyanide
  • Cyanic chloride
  • Chlorocyanogen
  • Chlorcyan
  • Chlorocyanide
Identifiers
3D model (JSmol)
AbbreviationsCK
ChemSpider
ECHA InfoCard 100.007.321 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-052-8
MeSH cyanogen+chloride
PubChem CID
RTECS number
  • GT2275000
UNII
UN number 1589
  • InChI=1S/CClN/c2-1-3 Yes check.svgY
    Key: QPJDMGCKMHUXFD-UHFFFAOYSA-N Yes check.svgY
  • ClC#N
Properties [1]
CNCl
Molar mass 61.470 g mol−1
AppearanceColorless gas
Odor acrid
Density 2.7683 mg mL−1 (at 0 °C, 101.325 kPa)
Melting point −6.55 °C (20.21 °F; 266.60 K)
Boiling point 13 °C (55 °F; 286 K)
soluble
Solubility soluble in ethanol, ether
Vapor pressure 1.987 MPa (at 21.1 °C)
-32.4·10−6 cm3/mol
Thermochemistry
Std molar
entropy (S⦵298)
236.33 J K−1 mol−1
137.95 kJ mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly toxic; [2] forms cyanide in the body [3]
GHS labelling:
GHS-pictogram-bottle.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
Danger
NFPA 704 (fire diamond)
4
0
2
Flash point nonflammable [3]
NIOSH (US health exposure limits):
PEL (Permissible)
none [3]
REL (Recommended)
C 0.3 ppm (0.6 mg/m3) [3]
IDLH (Immediate danger)
N.D. [3]
Safety data sheet (SDS) inchem.org
Related compounds
Related alkanenitriles
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Cyanogen chloride is a highly toxic chemical compound with the formula CNCl. This linear, triatomic pseudohalogen is an easily condensed colorless gas. More commonly encountered in the laboratory is the related compound cyanogen bromide, a room-temperature solid that is widely used in biochemical analysis and preparation.

Contents

Synthesis, basic properties, structure

Cyanogen chloride is a molecule with the connectivity Cl−C≡N. Carbon and chlorine are linked by a single bond, and carbon and nitrogen by a triple bond. It is a linear molecule, as are the related cyanogen halides (NCF, NCBr, NCI). Cyanogen chloride is produced by the oxidation of sodium cyanide with chlorine. This reaction proceeds via the intermediate cyanogen ((CN)2). [4]

The compound trimerizes in the presence of acid to the heterocycle called cyanuric chloride.

Cyanogen chloride is slowly hydrolyzed by water at neutral pH to release cyanate and chloride ions:

Applications in synthesis

Cyanogen chloride is a precursor to the sulfonyl cyanides [5] and chlorosulfonyl isocyanate, a useful reagent in organic synthesis. [6]

Safety

Also known as CK, cyanogen chloride is a highly toxic blood agent, and was once proposed for use in chemical warfare. It causes immediate injury upon contact with the eyes or respiratory organs. Symptoms of exposure may include drowsiness, rhinorrhea (runny nose), sore throat, coughing, confusion, nausea, vomiting, edema, loss of consciousness, convulsions, paralysis, and death. [2] It is especially dangerous because it is capable of penetrating the filters in gas masks, according to United States analysts. CK is unstable due to polymerization, sometimes with explosive violence. [7]

Chemical weapon

Cyanogen chloride is listed in schedule 3 of the Chemical Weapons Convention: all production must be reported to the OPCW. [8]

By 1945, the U.S. Army's Chemical Warfare Service developed chemical warfare rockets intended for the new M9 and M9A1 Bazookas. An M26 Gas Rocket was adapted to fire cyanogen chloride-filled warheads for these rocket launchers. [9] As it was capable of penetrating the protective filter barriers in some gas masks, [10] it was seen as an effective agent against Japanese forces (particularly those hiding in caves or bunkers) because their standard issue gas masks lacked the barriers that would provide protection against cyanogen chloride. [9] [11] [12] The US added the weapon to its arsenal, and considered using it, along with hydrogen cyanide, as part of Operation Downfall, the planned invasion of Japan, but President Harry Truman decided against it, instead using the atomic bombs developed by the secret Manhattan Project. [13] The CK rocket was never deployed or issued to combat personnel. [9]

Related Research Articles

<span class="mw-page-title-main">Phosgene</span> Toxic gaseous compound (COCl2)

Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of as formaldehyde with the hydrogen atoms replaced by chlorine atoms. Phosgene is a valued and important industrial building block, especially for the production of precursors of polyurethanes and polycarbonate plastics.

<span class="mw-page-title-main">Sodium cyanide</span> Chemical compound

Sodium cyanide is a poisonous compound with the formula NaCN. It is a white, water-soluble solid. Cyanide has a high affinity for metals, which leads to the high toxicity of this salt. Its main application, in gold mining, also exploits its high reactivity toward metals. It is a moderately strong base.

<span class="mw-page-title-main">Sodium hypochlorite</span> Chemical compound (known in solution as bleach)

Sodium hypochlorite, commonly known in a dilute solution as (chlorine) bleach, is an inorganic chemical compound with the formula NaOCl, comprising a sodium cation and a hypochlorite anion. It may also be viewed as the sodium salt of hypochlorous acid. The anhydrous compound is unstable and may decompose explosively. It can be crystallized as a pentahydrate NaOCl·5H
2O, a pale greenish-yellow solid which is not explosive and is stable if kept refrigerated.

<span class="mw-page-title-main">Phenacyl chloride</span> Chemical compound

Phenacyl chloride, also commonly known as chloroacetophenone, is a substituted acetophenone. It is a useful building block in organic chemistry. Apart from that, it has been historically used as a riot control agent, where it is designated CN. It should not be confused with cyanide, another agent used in chemical warfare, which has the chemical structure CN−.

<span class="mw-page-title-main">Diphosgene</span> Chemical compound

Diphosgene is an organic chemical compound with the formula ClCO2CCl3. This colorless liquid is a valuable reagent in the synthesis of organic compounds. Diphosgene is related to phosgene and has comparable toxicity, but is more conveniently handled because it is a liquid, whereas phosgene is a gas.

Cyanogen is the chemical compound with the formula (CN)2. The simplest carbon nitride, it is a colorless and highly toxic gas with a pungent odor. The molecule is a pseudohalogen. Cyanogen molecules consist of two CN groups – analogous to diatomic halogen molecules, such as Cl2, but far less oxidizing. The two cyano groups are bonded together at their carbon atoms: N≡C‒C≡N, although other isomers have been detected. The name is also used for the CN radical, and hence is used for compounds such as cyanogen bromide (NCBr) (but see also Cyano radical.)

<span class="mw-page-title-main">Allyl chloride</span> Chemical compound

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.

Pseudohalogens are polyatomic analogues of halogens, whose chemistry, resembling that of the true halogens, allows them to substitute for halogens in several classes of chemical compounds. Pseudohalogens occur in pseudohalogen molecules, inorganic molecules of the general forms Ps–Ps or Ps–X, such as cyanogen; pseudohalide anions, such as cyanide ion; inorganic acids, such as hydrogen cyanide; as ligands in coordination complexes, such as ferricyanide; and as functional groups in organic molecules, such as the nitrile group. Well-known pseudohalogen functional groups include cyanide, cyanate, thiocyanate, and azide.

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

<span class="mw-page-title-main">Copper(II) chloride</span> Chemical compound

Copper(II) chloride is the chemical compound with the chemical formula CuCl2. The anhydrous form is pinkish brown but slowly absorbs moisture to form a Black-green dihydrate.

<span class="mw-page-title-main">Thionyl chloride</span> Inorganic compound (SOCl2)

Thionyl chloride is an inorganic compound with the chemical formula SOCl2. It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.

<span class="mw-page-title-main">Phosphorus pentachloride</span> Chemical compound

Phosphorus pentachloride is the chemical compound with the formula PCl5. It is one of the most important phosphorus chlorides, others being PCl3 and POCl3. PCl5 finds use as a chlorinating reagent. It is a colourless, water-sensitive and moisture-sensitive solid, although commercial samples can be yellowish and contaminated with hydrogen chloride.

<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

<span class="mw-page-title-main">Cyanate</span> Anion with formula OCN and charge –1

Cyanate is an anion with the structural formula [O=C=N]−, usually written OCN−. It also refers to any salt containing it, such as ammonium cyanate.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

<span class="mw-page-title-main">Chromyl chloride</span> Chemical compound

Chromyl chloride is an inorganic compound with the formula CrO2Cl2. It is a reddish brown compound that is a volatile liquid at room temperature, which is unusual for transition metal complexes.

The Gattermann reaction, (also known as the Gattermann formylation and the Gattermann salicylaldehyde synthesis) is a chemical reaction in which aromatic compounds are formylated by a mixture of hydrogen cyanide (HCN) and hydrogen chloride (HCl) in the presence of a Lewis acid catalyst such as AlCl3. It is named for the German chemist Ludwig Gattermann and is similar to the Friedel–Crafts reaction.

<span class="mw-page-title-main">Sulfur tetrafluoride</span> Chemical compound

Sulfur tetrafluoride is the chemical compound with the formula SF4. It is a colorless corrosive gas that releases dangerous HF upon exposure to water or moisture. Despite these unwelcome characteristics, this compound is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries.

<span class="mw-page-title-main">Chlorosulfonyl isocyanate</span> Chemical compound

Chlorosulfonyl isocyanate is the chemical compound ClSO2NCO, known as CSI. This compound is a versatile reagent in organic synthesis.

A cyanogen halide is a molecule consisting of cyanide and a halogen. Cyanogen halides are chemically classified as pseudohalogens.

References

  1. ↑ Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, FL: CRC Press. ISBN   0-8493-0487-3.
  2. 1 2 "CYANOGEN CHLORIDE (CK)". The Emergency Response Safety and Health Database. NIOSH. 9 July 2021.
  3. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0162". National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ Coleman, G. H.; Leeper, R. W.; Schulze, C. C. (1946). "Cyanogen Chloride". Inorganic Syntheses. Inorganic Syntheses. Vol. 2. pp. 90–94. doi:10.1002/9780470132333.ch25. ISBN   9780470132333.
  5. ↑ Vrijland, M. S. A. (1977). "Sulfonyl Cyanides: Methanesulfonyl Cyanide" (PDF). Organic Syntheses . 57: 88.; Collective Volume, vol. 6, p. 727
  6. ↑ Graf, R. (1966). "Chlorosulfonyl Isocyanate" (PDF). Organic Syntheses . 46: 23.; Collective Volume, vol. 5, p. 226
  7. ↑ FM 3-8 Chemical Reference Handbook. US Army. 1967.
  8. ↑ "Schedule 3". www.opcw.org. Retrieved 16 March 2018.
  9. 1 2 3 Smart, Jeffrey (1997), "2", History of Chemical and Biological Warfare: An American Perspective, Aberdeen, MD, USA: Army Chemical and Biological Defense Command, p. 32.
  10. ↑ "Cyanogen chloride (CK): Systemic Agent | NIOSH | CDC". 9 July 2021.
  11. ↑ "Characteristics and Employment of Ground Chemical Munitions", Field Manual 3-5, Washington, DC: War Department, 1946, pp. 108–19
  12. ↑ Skates, John R (2000), The Invasion of Japan: Alternative to the Bomb, University of South Carolina Press, pp. 93–96, ISBN   978-1-57003-354-4
  13. ↑ Binkov's Battlegrounds (27 April 2022). "How would have WW2 gone if the US had not used nuclear bombs on Japan?". YouTube.Com. Retrieved 23 June 2022.

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