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Tabun (nerve agent)

Tabun
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Names
IUPAC name
(RS)-Ethyl N,N-Dimethylphosphoramidocyanidate
Other names
GA; Ethyl dimethylphosphoramidocyanidate; Dimethylaminoethoxy-cyanophosphine oxide; Dimethylamidoethoxyphosphoryl cyanide; Ethyl dimethylaminocyanophosphonate; Ethyl ester of dimethylphosphoroamidocyanidic acid; Ethyl phosphorodimethylamidocyanidate; Cyanodimethylaminoethoxyphosphine oxide; Dimethylaminoethodycyanophosphine oxide; EA1205
Identifiers
77-81-6 N
3D model (Jmol) Interactive image
ChEMBL ChEMBL1097650 N
ChemSpider 6254 YesY
Properties
C5H11N2O2P
Molar mass 162.13 g·mol−1
Appearance Colorless to brown liquid
Density 1.0887 g/cm3 at 25 °C
1.102 g/cm3 at 20 °C
Melting point −50 °C (−58 °F; 223 K)
Boiling point 247.5 °C (477.5 °F; 520.6 K)
9.8 g/100 g at 25 °C
7.2 g/100 g at 20 °C
Vapor pressure 0.07 mmHg (9 Pa)
Hazards
Main hazards Highly toxic. Fires involving this chemical may result in the formation of hydrogen cyanide
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 78 °C (172 °F; 351 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Tabun or GA is an extremely toxic chemical substance. It is a clear, colorless, and tasteless liquid with a faint fruity odor. It is classified as a nerve agent because it fatally interferes with normal functioning of the mammalian nervous system. Its production is strictly controlled and stockpiling outlawed by the Chemical Weapons Convention of 1993. Tabun is the first of the G-series nerve agents along with GB (sarin), GD (soman) and GF (cyclosarin).

Although pure tabun is clear, less-pure tabun may be brown. It is a volatile chemical, although less so than either sarin or soman.

Tabun can be destroyed with bleaching powder (calcium hypochlorite), though the poisonous gas cyanogen chloride is produced.

Tabun was made on an industrial scale by Germany during World War II, based on a process developed by Gerhard Schrader. In the chemical agent factory in Dyhernfurth an der Oder, codenamed "Hochwerk", at least 12,000 metric tons of this agent were manufactured between 1942 and 1945. The manufacturing process consisted of two steps, the first being reaction of gaseous dimethylamine (1) with an excess of phosphoryl chloride (2), yielding dimethylamidophosphoric dichloride (3, codenamed "Produkt 39" or "D 4") and dimethylammonium chloride (4). The dimethylamidophosphoric dichloride thus obtained was purified by vacuum distillation and thereafter transferred to the main Tabun production line. Here it was reacted with an excess of sodium cyanide (5), dispersed in dry chlorobenzene, yielding the intermediate dimethylamidophosphoric dicyanide (not depicted in the scheme) and sodium chloride (8); then, absolute ethanol (6) was added, reacting with the dimethylamidophosphoric dicyanide to yield tabun (7) and hydrogen cyanide (9). After the reaction, the mixture (consisting of about 75% chlorobenzene and 25% tabun, along with insoluble salts and the rest of the hydrogen cyanide) was filtered to remove the insoluble salts and vacuum-distilled to remove hydrogen cyanide and excess chlorobenzene, so yielding the technical product, consisting either of 95% tabun with 5% chlorobenzene (Tabun A) or (later in the war) of 80% tabun with 20% chlorobenzene (Tabun B).


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