DIISOPROPYL FLUOROPHOSPHATE

Base Information

• Chemical Name: DIISOPROPYL FLUOROPHOSPHATE
• CAS No.: 55-91-4
• Deprecated CAS: 37209-35-1
• Molecular Formula: C6H14 F O3 P
• Molecular Weight: 184.148
• Hs Code.: 29209085
• European Community (EC) Number: 200-247-6
• UN Number: 2810,3018
• UNII: 12UHW9R67N
• DSSTox Substance ID: DTXSID1040667
• Nikkaji Number: J4.564K
• Wikipedia: Diisopropyl_fluorophosphate
• Wikidata: Q384993
• NCI Thesaurus Code: C65979
• Pharos Ligand ID: DAV4SGX7MXB6
• Metabolomics Workbench ID: 42992
• ChEMBL ID: CHEMBL1025
• Mol file: 55-91-4.mol

Synonyms:Phosphorofluoridicacid, diisopropyl ester (8CI); DFF; DFP; DFP (pesticide); Difluorophate;Diflupyl; Diisopropoxyphosphoryl fluoride; Diisopropyl fluorophosphate;Diisopropyl phosphofluoridate; Diisopropyl phosphorofluoridate; Dyflos;Floropryl; Fluorodiisopropyl phosphate; Fluostigmine; Isoflurophate; Isopropylfluophosphate ((C3H7O)2FPO); Isopropyl phosphorofluoridate ((C3H7O)2FPO);Neoglaucit; O,O-Diisopropyl phosphorofluoridate

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Chemical Property of DIISOPROPYL FLUOROPHOSPHATE

Chemical Property:

• Appearance/Colour: Colourless Liquid
• Vapor Pressure: 0.58 mm Hg ( 20 °C)
• Melting Point: −82 °C(lit.)
• Refractive Index: n20/D 1.385(lit.)
• Boiling Point: 62 °C9 mm Hg(lit.)
• Flash Point: 64.5°C
• PSA: 45.34000
• Density: 1.079g/cm³
• LogP: 2.91400
• Storage Temp.: 2-8°C
• Solubility.: Benzene (Slightly)
• Water Solubility.: 15.17g/L(25 oC)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 184.06645946
• Heavy Atom Count: 11
• Complexity: 144
• Transport DOT Label: Poison

Purity/Quality:

Safty Information:

• Pictogram(s): Cholinesterase inhibitor.
• Hazard Codes: T+,Xi
• Statements: 26/27/28-36/37/38
• Safety Statements: 36/37/39-45-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CC(C)OP(=O)(OC(C)C)F
• General Description: Diisopropyl fluorophosphate (DFP) is a nerve agent mimic that reacts with chromogenic probes, such as the synthesized chromoreactand 1, to induce a detectable colorimetric change (from yellow to colorless) due to intramolecular cyclization. This reaction, studied in acetonitrile and mixed water–acetonitrile solutions, demonstrates DFP's role as an organophosphorus (OP) simulant, with detection limits and kinetic properties comparable to other nerve agent mimics like diethyl chlorophosphate (DCP) and diethyl cyanophosphate (DCNP). The probe's selectivity and rapid response highlight DFP's utility in developing sensitive and practical detection methods for OP compounds.

Technology Process of DIISOPROPYL FLUOROPHOSPHATE

There total 15 articles about DIISOPROPYL FLUOROPHOSPHATE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

diisopropyl trimethylsily phosphite (24350-54-7) → diisopropyl phosphofluoridate (55-91-4)

Guidance literature:

With fluorosulfonylchloride; In dichloromethane; a) -50 deg C, 1 h, b) 20 deg C, 1 h;

Reference yield: 94.0%

diisopropyl hydrogenphosphonate (1809-20-7) → diisopropyl phosphofluoridate (55-91-4)

Guidance literature:

With 1,3-dichlorodimethylhydantoin-KF; In acetonitrile; at 20 ℃; for 0.333333h;

DOI:10.1016/j.jfluchem.2007.11.008

Reference yield: 85.0%

Diisopropyl chlorophosphate (2574-25-6) → diisopropyl phosphofluoridate (55-91-4)

Guidance literature:

With tetrabutylammonium tetra(tert-butyl alcohol) coordinate fluoride; In acetonitrile; at 70 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.03.151

upstream raw materials:

diisopropyl hydrogenphosphonate

Diisopropyl chlorophosphate

isopropyl phosphorodichloridate

isopropyl alcohol

Downstream raw materials:

N-(4-cyano-benzoyl)-O-(4-cyano-phenylcarbamoyl)-hydroxylamine

N-(4-nitro-benzoyl)-O-(4-nitro-phenylcarbamoyl)-hydroxylamine

diisopropoxyphosphoryloxy-carbamic acid phenyl ester

N-(4-bromo-benzyloxycarbonyl)-O-diisopropoxyphosphoryl-L-tyrosine

Refernces

Chromogenic detection of nerve agent mimics

10.1039/b811247a

The research focuses on the development of a new chromogenic protocol for the selective detection of nerve agent mimics, which are chemical compounds that simulate the behavior of actual nerve agents such as Tabun, Sarin, and Soman. The study addresses the need for quick and reliable detection methods due to the high toxicity and ease of production of these chemicals. The researchers synthesized a chromogenic probe, referred to as chromoreactand 1, using 2-(2-(dimethylamino)phenyl)ethanol (DAPE) as a building block. This probe was designed to undergo a colorimetric change upon interaction with certain organophosphorus (OP) substrates, which are nerve agent simulants. The probe's reactivity was tested with diethyl chlorophosphate (DCP), diisopropyl fluorophosphate (DFP), and diethyl cyanophosphate (DCNP) in acetonitrile. The reaction resulted in a hypsochromic shift, indicating a color change from yellow to colorless due to an intramolecular cyclization process. The detection limit for DCNP and DCP was found to be 1.0 x 10^-4 mol dm^-3. Further experiments involved the preparation of compound 2 to confirm the reaction mechanism through NMR spectroscopy. The probe's reactivity was also studied in mixed water–acetonitrile solutions at pH 7, showing selective bleaching in the presence of DCP, DFP, and DCNP. Kinetic studies were performed to determine the rate constants and half-life of the reaction. The potential application of the probe for in situ sensing was demonstrated by adsorbing it onto silica gel and testing its response to DCP vapor and solution. The study concludes that the developed chromoreactand is a promising alternative for the colorimetric detection of nerve agent simulants, showing selectivity and a rapid response.