DIISOPROPYL FLUOROPHOSPHATE

DIISOPROPYL FLUOROPHOSPHATE Basic information
Product Name:DIISOPROPYL FLUOROPHOSPHATE
Synonyms:Diflupyl;Diflurophate;Diisopropoxyphosphoryl fluoride;diisopropoxyphosphorylfluoride;Diisopropyl fluoridophosphate;Diisopropyl fluorophosphonate;Diisopropyl phosphofluoridate;Diisopropylfluorfosfat
CAS:55-91-4
MF:C6H14FO3P
MW:184.15
EINECS:200-247-6
Product Categories:All Inhibitors;Inhibitors
Mol File:55-91-4.mol
DIISOPROPYL FLUOROPHOSPHATE Structure
DIISOPROPYL FLUOROPHOSPHATE Chemical Properties
Melting point −82 °C(lit.)
Boiling point 62 °C9 mm Hg(lit.)
density 1.06 g/mL at 25 °C(lit.)
vapor pressure 0.58 mm Hg ( 20 °C)
refractive index n20/D 1.385(lit.)
storage temp. 2-8°C
solubility Benzene (Slightly)
form Oil
color Colourless to Light Yellow
Specific Gravity1.055 (25℃/4℃)
Water Solubility 15.17g/L(25 ºC)
Merck 13,5194
Stability:Stable. Moisture sensitive.
CAS DataBase Reference55-91-4(CAS DataBase Reference)
EPA Substance Registry SystemDiisopropyl fluorophosphate (55-91-4)
Safety Information
Hazard Codes T+,Xi
Risk Statements 26/27/28-36/37/38
Safety Statements 36/37/39-45-36/37-26
RIDADR UN 3382 6.1/PG 1
WGK Germany 3
RTECS TE5075000
10-21
HazardClass 6.1(a)
PackingGroup I
HS Code 29209085
Hazardous Substances Data55-91-4(Hazardous Substances Data)
ToxicityLD50 in mice (mg/kg): 3.71 s.c.; 36.8 orally (Horton)
MSDS Information
ProviderLanguage
SigmaAldrich English
DIISOPROPYL FLUOROPHOSPHATE Usage And Synthesis
Chemical PropertiesColourless Liquid
OriginatorFloropryl,MSD,US,1949
UsesDiisopropyl Fluorophosphate is a potent inhibitor of serine proteases such as trypsin and chymotrypsin, and of acetylcholinesterase. Diisopropyl fluorophosphate is a very potent neurotoxin.
UsesDFP served as a basis for developing nerve gases during World War II. It is not used as a nerve gas; it is employed as a pharmacology tool to investigate the toxic properties of nerve gases. It is applied as a miotic and in ophthalmic use.
DefinitionChEBI: Diisopropyl fluorophosphate is a dialkyl phosphate.
Manufacturing Process212 lb (3.54 lb-mols) of isopropanol containing less than 0.2 wt % of water was cooled with brine to -5°C in a jacketed reactor. 160 lb (1.16 lb-mols) of phosphorus trichloride was gradually added to the isopropanol with cooling and stirring during a period of 4 hours. The temperature of the reaction was not allowed to exceed 12°C and the system was maintained under slight negative pressure (about 700 mm) to remove undesirable vapors.
After completion of the addition, the mixture was stirred for ? hour and then subjected to a pressure of 12 to 100 mm of mercury. Chlorine was then passed into the crude reaction product at a rate of 12 lb/hr, the temperature of the reaction being kept below 12°C by brine cooling. The end of the reaction was indicated by a temperature drop which occurred after a total of 122 lb of chlorine (1.72 lb-mols, 48% excess) was used.
To remove excess chlorine, hydrogen chloride and isopropyl chloride, the wellstirred mixture was subjected to a pressure of 12 to 100 mm of mercury for 2 hours. The temperature was gradually raised to 20°C during this time by passing steam into the jacket of the reactor. 10 gallons of benzene was then added and distilled off under reduced pressure, gradually raising thetemperature of the reaction mixture to 30°C. The last traces of hydrogen chloride were removed by adding an additional 10 gallons of benzene which was distilled off under reduced pressure at reactor temperatures not exceeding 50°C. The total time required for the removal of the volatile acid components of the reaction mixture was 4 hours.
The mixture was then cooled to 20°C and 19 gallons of benzene was added. This was followed by the introduction of 123.5 lb (2.80 lb-mols) of dry powdered sodium fluoride (95% pure). The mixture was stirred and heated to the refluxing temperature in a period of 1 hour and held at this temperature (95° to 98°C) for 4 hours. The product obtained was cooled and filtered to yield a filter cake which was washed with three 5-gallon portions of benzene. The filtrate and washing were then combined and distilled under reduced pressure. There was obtained 158 lb (74% yield of theory based on PCl3) of diisopropyl fluorophosphate, BP 62°C at 9 mm and 46°C at 5 mm.
Brand nameFloropryl(Merck).
Therapeutic FunctionCholinergic (ophthalmic)
Synthesis Reference(s)Canadian Journal of Chemistry, 44, p. 501, 1966 DOI: 10.1139/v66-067
General DescriptionOily liquid. Clear, colorless or faintly yellow liquid. DIISOPROPYL FLUOROPHOSPHATE is used as a research tool in neuroscience for its ability to inhibit cholinesterase (by phosphorylation) on an acute/sub-acute basis and to produce a delayed neuropathy. An insecticide. Used in Germany as a basis for "nerve gases".
Air & Water ReactionsForms hydrogen fluoride in presence of moisture; decomposes in water at pH about 2.5.
Reactivity ProfileOrganophosphates, such as DIISOPROPYL FLUOROPHOSPHATE, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
Health HazardThis is an organophosphate pesticide. Extremely toxic: probable oral lethal dose in humans is 5-50 mg/kg, between 7 drops and 1 teaspoonful for 70 kg person (150 lb.). The material is a cholinesterase inactivator. Even traces of the vapor cause pinpoint pupils.
Health HazardDFP is a highly toxic organophosphate. Its chemical structure is similar to that of sarin and soman. It is a potent inhibitor of acetylcholinesterase, and its toxic actions are lower but similar to those of sarin and soman. Subcutaneous administration of 1.5 mg/kg causedcholinergicsymptomsinrats,inducing a progressive dose-related necrosis (Dettbarn 1984). DFP administered to rats produced muscle fiber discharges from the peripheral nerves as well as from the central nervous system (Clinton et al. 1988). This was significantly reduced when the animals were pretreatedwithatropinemethylnitrate,ketamine, or phenytoin.
In humans, exposure to its vapors at 1.5 ppm concentration in air for 10 minutes may produce headache and constriction of the pupil of the eye.
LD50 value, oral(rabbits): 10 mg/kg (NIOSH 1986)
LD50 value, subcutaneous (rats): 2 mg/kg (NIOSH 1986).
Fire HazardMay burn but will not ignite readily. Container may explode in heat of fire. Fire and runoff from fire control water may produce irritating or poisonous gases. Forms hydrogen fluoride in presence of moisture; decomposes in water at pH about 2.5. Keep away from sources of heat. Anhydrous compounds or oil solutions are stable in glass containers at room temperature.
Biochem/physiol ActionsPotent inhibitor of serine proteases such as trypsin and chymotrypsin, and of acetylcholinesterase; also inhibits cathepsin G, cholinesterase, coagulation factor Xa, leucocyte elastase, pancreatic elastase, tissue kallikrein, plasmin, subtilisin, and thrombin. Inhibition of acetylcholinesterase makes this compound especially toxic. Inhibits apoptosis induced by ricin and bacterial toxins.
Waste DisposalIt is dissolved in a combustible solvent and burned in a chemical incinerator. It may be destroyed by treating with molten metal at 800-1000°C (1472-1832°F). It may be decomposed by treatment with dilute acid. Care should be taken, as highly toxic HF may be generated.
DIISOPROPYL FLUOROPHOSPHATE Preparation Products And Raw materials
Raw materialsSodium fluoride-->Isopropyl alcohol-->Phosphorus trichloride-->Chlorine
FLUOROPHOSPHORIC ACID PHOSPHORYL FLUORIDE PHOSPHONIC ACID, ETHYL METHYL ESTER Phosphoric acid BISMUTH TRIBROMOPHENATE DIISOPROPYLFLUOROPHOSPHATE, [1,3-3H]- Diethyl phosphite DIISOPROPYL FLUOROPHOSPHATE ISOPROPYL PHOSPHATE

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