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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Phenylarsonous dichloride | |||
| Other names Dichlorophenylarsane Dichloro(phenyl)arsine | |||
| Identifiers | |||
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3D model (JSmol) | |||
| Abbreviations | PD (NATO) | ||
| ChemSpider |
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| ECHA InfoCard | 100.010.721 | ||
| EC Number |
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| RTECS number |
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| UNII | |||
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| Properties | |||
| C6H5AsCl2 | |||
| Molar mass | 222.9315 g/mol | ||
| Appearance | Colorless liquid | ||
| Density | 1.65 g/cm3 (at 20 °C) | ||
| Melting point | −20 °C (−4 °F; 253 K) | ||
| Boiling point | 252 to 255 °C (486 to 491 °F; 525 to 528 K) | ||
| Reacts | |||
| Solubility | acetone, ether, benzene | ||
| logP | 3.060 | ||
| Vapor pressure | 0.033 | ||
Henry's law constant (kH) | 3.00E-05 atm·m3/mole | ||
Atmospheric OH rate constant | 1.95E-12 cm3/molecule·s | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | Flammability, incapacitation, blistering | ||
| NFPA 704 (fire diamond) | |||
| Flash point | 16 °C (61 °F; 289 K) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 2,500 mg·min/m3 | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | 0.5 mg/m2 | ||
| Safety data sheet (SDS) | New Jersey MSDS | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Phenyldichloroarsine, also known by its wartime namephenyl Dick[1] and itsNATO abbreviationPD, is anorganicarsenical vesicant and vomiting agent developed by Germany and France for use as achemical warfare agent duringWorld War I. The agent is known by multiple synonyms and is technically classified as a vesicant, orblister agent.
PD was prepared during 1917–18 in Germany and France, during World War II it was prepared in Germany.
Phenyldichloroarsine is an odorless, colorless substance that can formhydrochloric acid upon contact with water.[2] The reaction with water is very slow, the substance sinks, and the reaction is considered non-hazardous.[3] Another product ofhydrolysis is phenylarsenious acid, which is a severeirritant to themucous membranes andskin.[2] In an impure state, phenyldichloroarsine may have a slight brown color, in its purest form though there is no color and the substance has an oily texture.[4] An impure solution of PD also emits a characteristically unpleasanthorseradish orgarlic-like odor, which is detectable at 0.1 ppm.[5]
Phenyldichloroarsine is one of four organic arsenicals, the other three arelewisite (L),methyldichloroarsine (MD), andethyldichloroarsine (ED).[6] PD is considered ananalog of lewisite.[7] At itsfreezing point, -20 °C, PD becomes amicrocrystalline solid mass.[8] The compound has aC-metalloid bond between thephenyl group and the arsenic and twocovalent bonds between the arsenic and thechlorine.[9]
Phenyldichloroarsine is produced by reactingbenzene witharsenic trichloride. Anhydrousaluminum chloride acts as acatalyst in this reaction.[4]
Phenyldichloroarsine is an obsoletechemical warfare agent and is classified as avesicant or a vomiting/incapacitating agent.[10] It was used as a weapon during World War I, where it showed itself as less effective than other vomiting agents.[10] Phenyldichloroarsine is an arsenical vesicant which can be mixed with mustard agents for use in chemical warfare.[11]PD was developed for use in wet environments, because of its tendency to persist in cool and shaded areas.[12] Phenyldichloroarsine can have a persistence lasting anywhere from 2 to 7 days under usual environmental conditions.[4] In open areas, it is more useful as a vomiting agent but in closed-in areas, such as basements, trenches and caves, it is highly effective because of its "extreme" vapor density.[12] Phenyldichloroarsine has also been used by banks and other high-security facilities to defend against security breaches.[4]
PD damages the eyes, lungs, throat and nasal membranes.[12] PD immediately affects the eyes and blindness can result, though it requires high doses.[4] It also induces nausea and vomiting, an inhalation of as little as 5-50 milligrams can induce severe vomiting.[4] Long-term exposure to PD can cause systemic damage by replacing calcium witharsenic, extensivebone marrow damage can also result.[12] Due to PD being easily recognized in the field and a relatively fast rate for decontamination procedures to become effective, the chemical is not as useful as other blister agents.[4] The blistering resultant from PD exposure may also be delayed, for as little as 30 minutes,[7] or as long as 32 hours depending upon the concentration of the dose.[4]
The molecular toxicology of PD is not well understood,[7] but a 1986 U.S. Army-sponsored report did shed some light on that area. The Army report showed that PD penetrated thered blood cell membrane and interacted with something inside the cell. The study also found thathemoglobin was not responsible for "holding" the PD in its bond with the erythrocytes (red blood cells), insteadglutathione was found to be a more likely interacting with PD inside the cell.[7][12]
