Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

D0879

Sigma-Aldrich

Diisopropylfluorophosphate

Synonym(s):

DFP, DIFP, Diisopropyl phosphorofluoridate, Phosphoric acid diisopropyl ester fluoride

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
[(CH3)2CHO]2POF
CAS Number:
55-91-4
Molecular Weight:
184.15
Beilstein/REAXYS Number:
1723307
EC Number:
200-247-6
MDL number:
MFCD00008873
UNSPSC Code:
12352200
PubChem Substance ID:
24893303
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

100

vapor pressure

0.58 mmHg ( 20 °C)

form

liquid

refractive index

n20/D 1.385 (lit.)

bp

62 °C/9 mmHg (lit.)

mp

−82 °C (lit.)

solubility

anhydrous isopropanol: 0.1-0.5 M (stable for months if stored at -70 °C)
H2O: 1.5% at 25 °C (very unstable (at pH 7.5, half-life = 1 hr); decomposed by alkali.)

density

1.06 g/mL at 25 °C (lit.)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

CC(C)OP(F)(=O)OC(C)C

InChI

1S/C6H14FO3P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3

InChI key

MUCZHBLJLSDCSD-UHFFFAOYSA-N

Gene Information

human ... ACHE(43) , PTGS1(5742) , PTGS2(5743)

Looking for similar products? Visit Product Comparison Guide

Application

Diisopropylfluorophosphate has been used:
  • in combination with inactivated thrombin in Affi-Gel 10 column for the purification of recombinant human thrombomodulin with its chondroitin sulfate chain (shrTMCSA)
  • for inducing status epilepticus (SE) in adult rats
  • as an irreversible serine protease inhibitor in human neutrophil subcellular fractions

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 this compound especially toxic. Inhibits apoptosis induced by ricin and bacterial toxins.

Analysis Note

Typically used at a concentration of 0.10 mM. A safer alternative inhibitor for serine protease is phenylmethylsulfonyl fluoride (PMSF).

Other Notes

Stored properly at 2-8°C, in an unopened bottle, DIFP should be stable for a minimum of two years. DIFP
is unstable when exposed to moisture. DIFP will develop a dark yellow color upon decomposition.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Inhibition of the prostaglandin EP2 receptor is neuroprotective and accelerates functional recovery in a rat model of organophosphorus induced status epilepticus
Rojas A, et al.
Neuropharmacology, 93, 15-27 (2015)
Recombinant human thrombomodulincsa+: a tool for analyzing Plasmodium falciparum adhesion to chondroitin-4-sulfate
Parzy D, et al.
Microbes and Infection, 2(7), 779-788 (2000)
A molecular probe for the highly selective chromogenic detection of DFP, a mimic of Sarin and Soman nerve agents.
Raúl Gotor et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(43), 11994-11997 (2011-09-17)
Yonggang Li et al.
Toxicology and applied pharmacology, 262(2), 194-204 (2012-05-16)
Current medical countermeasures against organophosphate (OP) nerve agents are effective in reducing mortality, but do not sufficiently protect the CNS from delayed brain damage and persistent neurological symptoms. In this study, we examined the efficacy of neuregulin-1 (NRG-1) in protecting
A V Terry et al.
Neurotoxicology and teratology, 34(1), 1-8 (2011-10-26)
The acute toxicity of organophosphates (OPs) has been studied extensively; however, much less attention has been given to the subject of repeated exposures that are not associated with overt signs of toxicity (i.e., subthreshold exposures). The objective of this study
View All Related Papers

Articles

Elastase

Enzyme Explorer Product Application Index for Elastase. Leukocyte elastase is a 29KDa serine endoprotease of the Proteinase S1 Family. It exists as a single 238 amino acid-peptide chain with four disulfide bonds.

Chymotrypsin

Analytical Enzyme Chymotrypsin: Chymotrypsin is produced in the acinar cells of the pancreas as the inactive precursor, chymotrypsinogen.

Related Content

Trypsin Serine Protease Enzyme

Trypsin is an enzyme in the serine protease class that consists of a polypeptide chain of 223 amino acid residues. Multiple sources, grades and formulations of trypsin specifically designed for research applications are available.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service