55-91-4 Hazards Identification
Pictogram(s):
Signal:
Danger
GHS Hazard Statements:
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal]
H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]
Precautionary Statement Codes:
P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501
Hazard Classes and Categories:
Acute Tox. 2 (100%)
Acute Tox. 1 (100%)
Hazards Summary:
Produces hydrogen fluoride on exposure to moisture; Extremely toxic cholinesterase inactivator; [Merck Index] Causes irritation and injury to skin and eyes; Vapor highly irritating to eyes and mucous membranes and causes miosis in trace amounts; Cholinesterase inhibitor that is highly toxic by skin absorption and inhalation; Symptoms of heavy exposure could include convulsions, cyanosis, pulmonary edema, and coma; [EPA OHM/TADS] Effects in high-dose animal studies include miosis, true cholinesterase inhibition, fasciculations, convulsions, and coma; [RTECS] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]
55-91-4 Usage
Uses
Used in Pharmacology Research:
DFP is used as a pharmacology tool for investigating the toxic properties of nerve gases. It helps researchers understand the mechanisms of action and potential antidotes for these toxic substances.
Used in Ophthalmology:
DFP is applied as a miotic in ophthalmic use, which helps constrict the pupil and is used to treat certain eye conditions.
Used in Chemical Warfare Research:
DFP served as a basis for developing nerve gases during World War II. Although it is not used as a nerve gas itself, its study has contributed to the understanding and development of countermeasures against such agents.
Originator
Floropryl,MSD,US,1949
Manufacturing Process
212 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.
Therapeutic Function
Cholinergic (ophthalmic)
Synthesis Reference(s)
Canadian Journal of Chemistry, 44, p. 501, 1966 DOI: 10.1139/v66-067
Air & Water Reactions
Forms hydrogen fluoride in presence of moisture; decomposes in water at pH about 2.5.
Reactivity Profile
Organophosphates, 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 Hazard
This 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 Hazard
DFP 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 Hazard
May 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 Actions
Potent 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 DIISOPROPYL FLUOROPHOSPHATE especially toxic. Inhibits apoptosis induced by ricin and bacterial toxins.
Waste Disposal
It 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.
Check Digit Verification of cas no
The CAS Registry Mumber 55-91-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 5 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 55-91:
(4*5)+(3*5)+(2*9)+(1*1)=54
54 % 10 = 4
So 55-91-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H14FO3P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3
55-91-4Relevant academic research and scientific papers
Purohit, Ajay Kumar,Pardasani, Deepak,Kumar, Ajeet,Goud, D. Raghavender,Jain, Rajiv,Dubey
, p. 4593 - 4595 (2015)
An efficient synthetic method has been developed to obtain dialkyl fluorophosphates from dialkylphosphites using inorganic reagent (CuCl2 and CsF) at room temperature.
Synthesis and Storage Stability of Diisopropylfluorophosphate
Heiss, Derik R.,Zehnder, Donald W.,Jett, David A.,Platoff, Gennady E.,Yeung, David T.,Brewer, Bobby N.
, (2016/07/06)
Diisopropylfluorophosphate (DFP) is a potent acetylcholinesterase inhibitor commonly used in toxicological studies as an organophosphorus nerve agent surrogate. However, LD50 values for DFP in the same species can differ widely even within the same laboratory, possibly due to the use of degraded DFP. The objectives here were to identify an efficient synthesis route for high purity DFP and assess the storage stability of both the in-house synthesized and commercial source of DFP at the manufacturer-recommended storage temperature of 4°C, as well as -10°C and -80°C. After 393 days, the commercial DFP stored at 4°C experienced significant degradation, while only minor degradation was observed at -10°C and none was observed at -80°C. DFP prepared using the newly identified synthesis route was significantly more stable, exhibiting only minor degradation at 4°C and none at -10°C or -80°C. The major degradation product was the monoacid derivative diisopropylphosphate, formed via hydrolysis of DFP. It was also found that storing DFP in glass containers may accelerate the degradation process by generating water in situ as hydrolytically generated hydrofluoric acid attacks the silica in the glass. Based on the results here, it is recommended that DFP be stored at or below -10°C, preferably in air-tight, nonglass containers.
Tetrabutylammonium tetra (tert-butyl alcohol) coordinated fluoride-an efficient reagent for the synthesis of fluorine derivatives of phosphorus(V) compounds
Gupta, Hemendra K.,Pardasani, Deepak,Mazumder, Avik,Purohit, Ajay Kumar,Dubey, Devendra K.
experimental part, p. 2697 - 2699 (2009/08/09)
Direct conversion of phosphorus(V) chlorides to the corresponding phosphorus(V) fluorides was achieved using a solid reagent, tetrabutylammonium tetra (tert-butyl alcohol) coordinated fluoride. The phosphorus(V) fluorides were directly synthesized and efficiently isolated in very good yields.
Dichlorodimethylhydantoin-KF as an efficient reagent for one pot synthesis of dialkylfluorophosphates from dialkylphosphites
Gupta,Acharya,Dubey,Kaushik
, p. 226 - 229 (2008/09/16)
Organic-inorganic hybrid reagent dichlorodimethylhydantoin-KF (DCDMH-KF) mixture was explored as an efficient reagent for the direct conversion of dialkylphosphites to their corresponding dialkylfluorophosphates at room temperature and in shorter reaction times through a facile electrophilic-nucleophilic metathesis.
Trichloroisocyanuric acid-KF as an efficient reagent for one-pot synthesis of dialkylfluorophosphates from dialkylphosphites
Acharya,Gupta,Pardasani, Deepak,Dubey,Kaushik
, p. 3760 - 3765 (2008/12/23)
Trichloroisocyanuric acid-KF afforded dialkylfluorophosphates from dialkylphosphites at room temperature through a facile electrophilic- nucleophilic metathesis. Copyright Taylor & Francis Group, LLC.
Single step fluorination of dialkylphosphites: trichloroacetonitrile-KF as an efficient reagent for the synthesis of dialkyl fluorophosphates
Gupta,Acharya,Pardasani,Dubey
, p. 2232 - 2235 (2008/09/19)
The use of trichloroacetonitrile and KF mixture is described as an efficient reagent for the direct conversion of dialkylphosphites to their corresponding dialkyl fluorophosphates via in situ formation of dialkyl chlorophosphates in one-pot.
Rapid and efficient solid-supported reagent synthesis of fluorine derivatives of phosphorus(V) compounds
Sierakowski, Timothy,Kiddle, James J.
, p. 2215 - 2217 (2007/10/03)
Direct conversion of phosphorus(V) chlorides to the corresponding phosphorus(V) fluorides was achieved utilizing a solid-supported reagent. The phosphorus(V) fluorides were straightforwardly synthesized and efficiently isolated in very good yields.
PHOSPHORYLNITRILE OXIDES. 5. REACTIONS OF 3-(DIALKOXYPHOSPHORYL)ISOXAZOLES AND -ISOXAZOLINES WITH NUCLEOPHILIC REAGENTS
Pavlov, V. A.,Kurdyukov, A. I.,Gorin, B. I.,Sagitova, F. R.,Aristova, N. V.,et al.
, p. 718 - 723 (2007/10/02)
3-Phosphorylated isoxazoles and isoxazolines react with nucleophiles either with cleavage of the P-C bond and subsequent ring opening or with retention of the heterocyclic ring depending on the structure of the ring substituents, nature of the nucleophile, and reaction conditions.This permits the selective chemical modification of the starting compounds.
POLYHALOMETHANE REACTIONS WITH PHOSPHITE ANIONS: FLUOROPHILIC REACTIVITY OF PHOSPHORUS
Blackburn, G. Michael,Guo, Mao-Jun,Taylor, Steven
, p. 139 - 142 (2007/10/02)
Di-isopropyl phosphite reacts with bromotrifluoromethane under basic conditions giving a mixture of some seven products.Identification of these by high-resolution NMR and MS shows that 80 percent of all products are formed by displacement of fluorine from
Fluorination of Trimethylsilyl Phosphites and their Structural Analogues by Sulfuryl Chloride Fluoride: Simple Preparation of Phosphorofluoridates and Related Compounds, including Deoxynucleoside Phosphorofluoridates
Dabkowski, Wojciech,Cramer, Friedrich,Michalski, Jan
, p. 1447 - 1452 (2007/10/02)
Trimethylsilyl esters of general formula RR'POSiMe3 react in a quantitative and fully chemoselective way with sulfuryl chloride fluoride, ClSO2F, under extremely mild conditions to give phosphorofluoridates RO(R'O)P(O)F of high purity.This work provides easy access to all type of fluoridates from non-toxic starting materials.The synthetic usefulness of this method is illustrated by the synthesis of 3'- and 5'-mononucleoside phosphorofluoridates 10 and 3',5'-dinucleoside phosphorofluoridates 11 from the corresponding nucleoside trimethylsilyl phosphites.
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