2-Chloroethyl ethyl sulfide

Last updated
2-Chloroethyl ethyl sulfide
Chloroethyl ethyl sulfide.svg
Names
Preferred IUPAC name
1-Chloro-2-(ethylsulfanyl)ethane
Other names
1-Chloro-2-(ethylthio)ethane, 2-(Ethylthio)chloroethane 2-Chlorodiethyl sulfide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.010.676 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-742-1
PubChem CID
UNII
  • InChI=1S/C4H9ClS/c1-2-6-4-3-5/h2-4H2,1H3
    Key: GBNVXYXIRHSYEG-UHFFFAOYSA-N
  • CCSCCCl
Properties
C4H9ClS
Molar mass 124.63 g·mol−1
Appearancecolorless liquid
Density 1.0663 g/cm3
Boiling point 156 °C (313 °F; 429 K)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H226, H301, H302, H311, H314, H331, H350
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Chloroethyl ethyl sulfide is the organosulfur compound with the formula C2H5SC2H4Cl. It is a colorless liquid. The compound is part of the family of vesicant compounds known as half mustards, has been heavily investigated because of its structural similarity to the sulfur mustard S(C2H4Cl)2. The LD50s of the half and full mustard are 252 and 2.4 mg/kg (oral, rats). [1]

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Mustard gas Chemical compound once used in warfare

Mustard gas or sulfur mustard is a chemical compound belonging to a family of cytotoxic and blister agents known as mustard agents. The name mustard gas is widely used, but it is technically incorrect: the substance, when dispersed, is often not actually in a vapor, but is instead in the form of a fine mist of liquid droplets.

An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class provides common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.

Copper(I) chloride Chemical compound

Copper(I) chloride, commonly called cuprous chloride, is the lower chloride of copper, with the formula CuCl. The substance is a white solid sparingly soluble in water, but very soluble in concentrated hydrochloric acid. Impure samples appear green due to the presence of copper(II) chloride (CuCl2).

Polysulfide

Polysulfides are a class of chemical compounds containing chains of sulfur atoms. There are two main classes of polysulfides: inorganic and organic. Among the inorganic polysulfides, there are ones which contain anions, which have the general formula S2−
n
. These anions are the conjugate bases of the hydrogen polysulfides H2Sn. Organic polysulfides generally have the formulae R1SnR2, where R = alkyl or aryl.

Thionyl chloride Chemical compound

Thionyl chloride is an inorganic compound with the chemical formula SOCl
2
. 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.

Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfur is essential for life. Of the 20 common amino acids, two are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries.

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Tetrasulfur tetranitride Chemical compound

Tetrasulfur tetranitride is an inorganic compound with the formula S4N4. This gold-poppy coloured solid is the most important binary sulfur nitride, which are compounds that contain only the elements sulfur and nitrogen. It is a precursor to many S-N compounds and has attracted wide interest for its unusual structure and bonding.

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Sulfur dichloride Chemical compound

Sulfur dichloride is the chemical compound with the formula SCl2. This cherry-red liquid is the simplest sulfur chloride and one of the most common, and it is used as a precursor to organosulfur compounds. It is a highly corrosive and toxic substance, and it reacts on contact with water to form chlorine-containing acids.

Chlorosulfuric acid Chemical compound

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Sulfur tetrafluoride 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.

Disulfur dichloride Chemical compound

Disulfur dichloride is the inorganic compound of sulfur and chlorine with the formula S2Cl2.

HN3 (nitrogen mustard) Chemical compound

Tris(2-chloroethyl)amine is the organic compound with the formula N(CH2CH2Cl)3. Often abbreviated HN3 or HN-3, it is a powerful blister agent and a nitrogen mustard used for chemical warfare. HN3 was the last of the nitrogen mustard agents developed. It was designed as a military agent and is the only one of the nitrogen mustards that is still used for military purposes. It is the principal representative of the nitrogen mustards because its vesicant properties are almost equal to those of HD and thus the analogy between the two types of mustard is the strongest. As a vesicant the use and production is strongly restricted within the Chemical Weapons Convention where it is classified as a Schedule 1 substance.

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Selenium monochloride Chemical compound

Selenium monochloride is an inorganic compound with the formula Se2Cl2. Although it is called selenium monochloride, a more descriptive name might be diselenium dichloride. It is a reddish-brown, oily liquid that hydrolyses slowly. It exists in chemical equilibrium with SeCl2, SeCl4, chlorine, and elemental selenium. Selenium monochloride is mainly used as a reagent for the synthesis of Se-containing compounds.

Sulfur chloride pentafluoride Chemical compound

Sulfur chloride pentafluoride is an inorganic compound with the formula SF
5
Cl
. It exists as a colorless gas at room temperature and is highly toxic, like most inorganic compounds containing the pentafluorosulfide (SF5) functional group. The compound adopts an octahedral geometry with C
4v
symmetry. Sulfur chloride pentafluoride is the only commercially available reagent for adding the SF
5
group to organic compounds.

Sulfur tetrachloride Chemical compound

Sulfur tetrachloride is an inorganic compound with chemical formula SCl4. It has only been obtained as an unstable pale yellow solid. The corresponding SF4 is a stable, useful reagent.

Bis(chloroethyl) ether is an organic compound with the formula O(CH2CH2Cl)2. It is an ether with two 2-chloroethyl substituents. It is a colorless liquid with the odor of a chlorinated solvent.

Lead(IV) chloride Chemical compound

Lead tetrachloride, also known as lead(IV) chloride, has the molecular formula PbCl4. It is a yellow, oily liquid which is stable below 0 °C, and decomposes at 50 °C. It has a tetrahedral configuration, with lead as the central atom. The Pb–Cl covalent bonds have been measured to be 247 pm and the bond energy is 243 kJ⋅mol−1.

References

  1. Wang, Qi-Qiang; Begum, Rowshan Ara; Day, Victor W.; Bowman-James, Kristin (2012). "Sulfur, Oxygen, and Nitrogen Mustards: Stability and Reactivity". Organic & Biomolecular Chemistry. 10 (44): 8786–8793. doi:10.1039/c2ob26482j. PMID   23070251.