Bis(2-chloroethyl)sulfide

Last updated
Mustard gas
Sulfur-mustard-2D-skeletal.svg
Sulfur-mustard-3D-balls.png
Sulfur-mustard-3D-vdW.png
Names
Preferred IUPAC name
1-Chloro-2-[(2-chloroethyl)sulfanyl]ethane
Other names
Bis(2-chloroethyl) sulfide
HD
Iprit
Schwefel-LOST
Lost
Sulfur mustard
Senfgas
Yellow cross liquid
Yperite
Distilled mustard
Mustard T- mixture
1,1'-thiobis[2-chloroethane]
Dichlorodiethyl sulfide
Identifiers
3D model (JSmol)
1733595
ChEBI
ChEMBL
ChemSpider
EC Number
  • 684-527-7
324535
KEGG
PubChem CID
UNII
  • InChI=1S/C4H8Cl2S/c5-1-3-7-4-2-6/h1-4H2 Yes check.svgY
    Key: QKSKPIVNLNLAAV-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H8Cl2S/c5-1-3-7-4-2-6/h1-4H2
    Key: QKSKPIVNLNLAAV-UHFFFAOYAK
  • ClCCSCCCl
Properties
C4H8Cl2S
Molar mass 159.07 g·mol−1
AppearanceColorless if pure. Normally ranges from pale yellow to dark brown. Slight garlic or horseradish type odor. [1]
Density 1.27 g/mL, liquid
Melting point 14.4 °C (57.9 °F; 287.5 K)
Boiling point 217 °C (423 °F; 490 K) begins to decompose at 217 °C (423 °F) and boils at 218 °C (424 °F)
7.6 mg/L at 20°C [2]
Solubility Alcohols, ethers, hydrocarbons, lipids, THF
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable, toxic, vesicant, carcinogenic, mutagenic
GHS labelling: [3]
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
Danger
H300, H310, H315, H319, H330, H335
P260, P261, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4
1
1
Flash point 105 °C (221 °F; 378 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
Nitrogen mustard, Bis(chloroethyl) ether, Chloromethyl methyl sulfide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Bis(2-chloroethyl)sulfide is the organosulfur compound with the formula (ClCH2CH2)2S. It is a prominent member of a family of cytotoxic and blister agents known as mustard agents. Sometimes referred to as mustard gas , the term is technically incorrect: bis(2-chloroethyl)sulfide is a liquid at room temperature. In warfare it was dispersed in the form of a fine mist of liquid droplets. [4] [5]

Contents

Synthesis

Bis(2-chloroethyl)sulfide has been prepared in a variety of ways. In the Depretz method, sulfur dichloride is treated with ethylene:

SCl2 + 2 C2H4 → (ClC2H4)2S

In the Levinstein process, disulfur dichloride is used instead: [6] [ failed verification ] [7]

S2Cl2 + 2 C2H4 → (ClC2H4)2S + 18 S8

In the Meyer method, thiodiglycol is produced from chloroethanol and potassium sulfide, and the resulting diol is then treated with phosphorus trichloride: [8] [9]

3 (HOC2H4)2S + 2 PCl3 → 3 (ClC2H4)2S + 2 P(OH)3

In the MeyerClarke method, concentrated hydrochloric acid (HCl) is used instead of PCl3:

(HOC2H4)2S + 2 HCl → (ClC2H4)2S + 2 H2O

Thionyl chloride and phosgene, the latter of which is also a choking agent, have also been used as chlorinating agents. These compounds have the added advantage in that if they are used in excess, they remain as impurities in the finished product and can therefore produce additional mechanisms of toxicity.

Reactions

The idealized combustion of mustard gas in oxygen produces hydrochloric acid and sulfuric acid, in addition to carbon dioxide and water:

(ClC2H4)2S + 7 O2 → 4 CO2 + 2 H2O + 2 HCl + H2SO4

Bis(2-chloroethyl)sulfide reacts with sodium hydroxide, giving divinyl sulfide:

(ClC2H4)2S + 2 NaOH → (CH2=CH)2S + 2 H2O + 2 NaCl

Sodium ethoxide acts similarly.

Safety

Upon skin contact or inhalation, bis(2-chloroethyl)sulfide is a nonspecific toxin. It is a strong alkylating agent, which affects DNA, RNA, and proteins. [10]

See also

Related Research Articles

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<span class="mw-page-title-main">Chlorine</span> Chemical element, symbol Cl and atomic number 17

Chlorine is a chemical element with the symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine.

<span class="mw-page-title-main">Mustard gas</span> Compound used in chemical warfare

Mustard gas or sulfur mustard is any of several chemical compounds that contain the chemical structure SCH2CH2Cl. In the wider sense, compounds with the substituent SCH2CH2X and NCH2CH2X are known as sulfur mustards and nitrogen mustards, respectively, (where X = Cl or Br). Such compounds are potent alkylating agents, which can interfere with several biological processes. Also known as mustard agents, this family of compounds are infamous cytotoxic and blister agents with a long history of use as chemical weapons. The name mustard gas is technically incorrect: the substances, when dispersed, are often not gases but a fine mist of liquid droplets. Sulfur mustards are viscous liquids at room temperature and have an odor resembling mustard plants, garlic, or horseradish, hence the name. When pure, they are colorless, but when used in impure forms, such as in warfare, they are usually yellow-brown. Mustard gases form blisters on exposed skin and in the lungs, often resulting in prolonged illness ending in death. The typical mustard gas is the organosulfur compound called bis(2-chloroethyl) sulfide.

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

Lewisite (L) (A-243) is an organoarsenic compound. It was once manufactured in the U.S., Japan, Germany and the Soviet Union for use as a chemical weapon, acting as a vesicant and lung irritant. Although the substance is colorless and odorless in its pure form, impure samples of lewisite are a yellow, brown, violet-black, green, or amber oily liquid with a distinctive odor that has been described as similar to geraniums.

<span class="mw-page-title-main">Sulfide (organic)</span> Organic compound with an –S– group

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

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References

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  2. Mustard agents: description, physical and chemical properties, mechanism of action, symptoms, antidotes and methods of treatment. Organisation for the Prohibition of Chemical Weapons. Accessed June 8, 2010.
  3. "Pubchem".
  4. https://www.acs.org/content/dam/acsorg/education/resources/highschool/chemmatters/gc-mustard-gas-personal-safety-and-natl-security.pdf [ bare URL PDF ]
  5. Ghabili, Kamyar; Agutter, Paul S.; Ghanei, Mostafa; Ansarin, Khalil; Panahi, Yunes; Shoja, Mohammadali M. (2011). "Sulfur mustard toxicity: History, chemistry, pharmacokinetics, and pharmacodynamics". Critical Reviews in Toxicology. 41 (5): 384–403. doi:10.3109/10408444.2010.541224. PMID   21329486. S2CID   28491672.
  6. Stewart, Charles D. (2006). Weapons of mass casualties and terrorism response handbook. Boston: Jones and Bartlett. p. 47. ISBN   0-7637-2425-4.
  7. "Chemical Weapons Production and Storage". Federation of American Scientists. Archived from the original on August 11, 2014.
  8. E. M. Faber and G. E. Miller (1932). "β-Thiodiglycol". Organic Syntheses. 12: 68. doi:10.15227/orgsyn.012.0068.
  9. Institute of Medicine (1993). Chapter 5: Chemistry of Sulfur Mustard and Lewisite. ISBN   0-309-04832-X.{{cite book}}: |work= ignored (help)
  10. Kehe, Kai; Szinicz, Ladislaus (2005). "Medical aspects of sulphur mustard poisoning". Toxicology. 214 (3): 198–209. doi:10.1016/j.tox.2005.06.014. PMID   16084004.