Methylphosphonyl difluoride
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name Methylphosphonic difluoride | |||
Other names Methylphosphonyl difluoride Methylphosphonoyl difluoride, EA-1251 | |||
Identifiers | |||
CAS Number |
| ||
3D model (JSmol) |
| ||
Beilstein Reference | 4-04-00-03508 | ||
ChemSpider |
| ||
MeSH | difluoride Methylphosphonic difluoride | ||
PubChem CID |
| ||
UNII |
| ||
CompTox Dashboard (EPA) |
| ||
InChI
| |||
| |||
Properties | |||
Chemical formula | CH3POF2 | ||
Molar mass | 100.00 | ||
Appearance | Colorless liquid | ||
Odor | Pungent, acid-like[1] | ||
Density | 1.359 g/mL (77°F)[1] | ||
Melting point | −37 °C; −35 °F; 236 K | ||
Boiling point | 100 °C; 212 °F; 373 K | ||
Solubility in water | Decomposes[1] | ||
Vapor pressure | 36 mmHg (77°F)[1] | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards | Corrosive, toxic | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Methylphosphonyl difluoride (DF), also known as EA-1251[2] or difluoro,[3] is a chemical weapon precursor. Its chemical formula is CH3POF2. It is a Schedule 1 substance under the Chemical Weapons Convention. It is used for production of sarin and soman as a component of binary chemical weapons; an example is the M687 artillery shell, where it is used together with a mixture of isopropyl alcohol and isopropyl amine, producing sarin.
Preparation
Methylphosphonyl difluoride can be prepared by reacting methylphosphonyl dichloride with hydrogen fluoride (HF) or sodium fluoride (NaF).
Safety
Methylphosphonyl difluoride is both reactive and corrosive. It is absorbed through skin and causes burns and mild nerve agent symptoms. It reacts with water, producing HF fumes and methylphosphonic acid as a result. It is also capable of corroding glass.
Significance in international relations
In 2013–2014, the stockpile of chemicals covered by the CWC was removed from Syria and destroyed. Of the stockpile, 581 tons (over 96%) of the stockpile was DF. It was destroyed by the U.S. Army on the MV Cape Ray by hydrolysis.[4][5]
References
- ^ a b c d e f Handbook of chemical and biological warfare agents (2nd ed.). CRC Press. 24 August 2007. ISBN 9780849314346.
- ^ "Physical properties of standard agents, candidate agents, and related compounds at several temperatures" (PDF). Archived (PDF) from the original on February 26, 2017.
- ^ U. S. Army (12 Dec 1990). Potential Military Chemical/Biological Agents and Compounds (PDF). Washington, D.C.: Headquarters, Dept. of the Army. Retrieved 12 May 2020.
- ^ Organization for the Prohibition of Chemical Weapons (OPCW). "U.S. Completes Destruction of Sarin Precursors from Syria on the Cape Ray". OPCW News. Retrieved 12 May 2020.
- ^ Trapp, Dr. Ralf. "Lessons Learned from the OPCW Mission in Syria" (PDF). OPCW. Retrieved 12 May 2020.
- v
- t
- e
- Agents used in chemical warfare
- incapacitation
- riot control
- Cyanogen
- Cyanogen bromide
- Cyanogen chloride (CK)
- Hydrogen cyanide (AC)
- Arsine
- Cacodyl cyanide
- Cacodyl oxide
- Hydrogen sulfide
- Phosphine
- Carbon monoxide
- Phosphorus trifluoride
- Methyl cyanoformate
- Iron pentacarbonyl
- Nickel tetracarbonyl
- 2,3,7,8-Tetrachlorodibenzodioxin
- Glycolonitrile
- Lactonitrile
- Acetone cyanohydrin
- Stibine
- Chloral cyanohydrin
Arsenicals | |
---|---|
Sulfur mustards |
|
Nitrogen mustards | |
Nettle agents |
|
Other |
G-agents |
|
---|---|
V-agents |
|
GV agents |
|
Novichok agents | |
Carbamates | |
Other | |
Precursors |
|
- Anatoxin-a
- Saxitoxin (TZ)
- Bungarotoxin
- Botulinum toxin (BTX)
- Tetanospasmin (TeNT)
- Ryanodine
- Ciguatoxin (CTX)
- Guanitoxin (GTX)
- Chlorophenylsilatrane
- Palytoxin (PTX)
- Maitotoxin (MTX)
- Tetrodotoxin
- Aconitine
- Brevetoxin (PbTX)
- Strychnine
- Antillatoxin (ATX)
- Tetraethyllead
- Dimethylmercury
- HN1 hydrochloride
- HN2 hydrochloride
- HN3 hydrochloride
- A-8564
- Picrotoxin
- Sulfuryl fluoride
- Tremorine
- Oxotremorine
- Batrachotoxin
- Tetramethylenedisulfotetramine (TETS)
- Bicyclic phosphates
- Cloflubicyne
- Trimethylolpropane phosphite
- Domoic acid
choking agents
- Chlorine
- Bromine
- Phosgene (CG)
- Fluorine
- Perfluoroisobutene
- Chloropicrin (PS)
- Dimethyl(trifluoromethylthio)arsine
- Diphosgene (DP)
- Disulfur decafluoride (Z)
- Acrolein
- Ethyl bromoacetate
- Perchloromethyl mercaptan
- Phenylcarbylamine chloride
- Tetranitromethane
- Tetrachlorodinitroethane
- Chlorine trifluoride
- Perchloryl fluoride
- Cadmium oxide
- Cadmium chloride
- Mercuric chloride
- Selenium dioxide
- Selenoyl fluoride
- Trifluoronitrosomethane
- Trichloronitrosomethane
- Nitric oxide
- Nitrogen dioxide
- Dinitrogen tetroxide
- Sulfur dioxide
- Phosphorus trichloride
- Methyl isocyanate
- Ethenone
- Methyl vinyl ketone
- Trifluoroacetyl chloride
- Salcomine
- Fluomine
- Uranium hexafluoride
- Diborane
- Green Cross
agents
- BZ (CS-4030)
- Apomorphine
- Butyrophenone
- EA-4941 (CS-4640)
- Etorphine
- EA-2092
- CS-4297
- Etoxadrol
- Dimethylheptylpyran (DMHP)
- EA-2148
- EA-3167
- EA-3443
- Pethidine
- EA-3580
- Ibogaine
- EA-3834
- Kolokol-1
- LSD-25
- PAVA spray
- Psilocybin
- Sleeping gas
- Carfentanil
- JB-318
- JB-336
- CS-27349
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,668
- Benperidol
- Desflurane
- Enflurane
- Bufotenin
- Isoflurane
- Halothane
- Sevoflurane
- Pentazocine
- Procarbazine
- Fluphenazine
- Chlorpromazine
agents
- Xylyl bromide
- Pepper spray (OC)
- Mace (spray)
- CN
- CS
- CR
- CNS
- Benzyl chloride
- Benzyl bromide
- Benzyl iodide
- Bromobenzyl cyanide
- Thiophosgene
- Chloroacetone
- Bromoacetone
- Bromomethyl ethyl ketone
- Acrolein
- Phenacyl bromide
- Chloroacetophenone oxime
- Ethyl bromoacetate
- Ethyl iodoacetate
- Iodoacetone
- Allyl isothiocyanate
- Hexamethylene diisocyanate
- Crotonaldehyde
- Abrin
- Aconitine
- Cyclopiazonic acid
- Histrionicotoxins
- Aflatoxins
- Anatoxin-a
- Batrachotoxin
- Botulinum toxin
- Brevetoxin
- Ciguatoxin
- Domoic acid
- Enterotoxin type B
- Grayanotoxin
- Guanitoxin
- Maitotoxin
- Modeccin
- Palytoxin
- Ricin
- Saxitoxin
- Shiga toxin
- T-2 mycotoxin
- Tetanospasmin
- Tetrodotoxin
- Volkensin
- Veratridine
- Methyl fluoroacetate
- Napalm (variants and mixtures)
- Fluoroethyl fluoroacetate
- Depleted uranium
- post-combustion uranium oxides
- Plutonium and its compounds
- Polonium
- White phosphorus