38399

Sigma-Aldrich

Diisopropylfluorophosphate

≥97.0% (GC)

Synonym(s):
Diisopropyl phosphorofluoridate, Phosphoric acid diisopropyl ester fluoride, DFP, DIFP
Linear Formula:
(CH3)2CHO2POF
CAS Number:
Molecular Weight:
184.15
Beilstein/REAXYS Number:
1723307
EC Number:
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

vapor pressure

0.58 mmHg ( 20 °C)

assay

≥97.0% (GC)

refractive index

n20/D 1.385 (lit.)

bp

62 °C/9 mmHg (lit.)

mp

−82 °C (lit.)

density

1.06 g/mL at 25 °C (lit.)

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)

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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

Potent inhibitor of chymotrypsin and other enzymes (e.g. serine hydrolases); Inhibition of carboxypeptidase but not DAP I

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T+

Risk Statement

26/27/28

Safety Statement

36/37/39-45

RIDADR

UN 3382 6.1 / PGI

WGK Germany

3

J.A. Cohen et al.
Methods in Enzymology, XI, 686-686 (1967)
J.K. McDonald et al.
Methods in Enzymology, XV(B), 275-275 (1972)
T V Damodaran et al.
Toxicology and applied pharmacology, 256(3), 348-359 (2011-08-16)
Organophosphorus-ester induced delayed neurotoxicity (OPIDN) is a neurodegenerative disorder characterized by ataxia progressing to paralysis with a concomitant central and peripheral, distal axonapathy. Diisopropylphosphorofluoridate (DFP) produces OPIDN in the chicken that results in mild ataxia in 7-14 days and severe...
Marko S Todorovic et al.
Epilepsy research, 101(3), 268-276 (2012-05-15)
Organophosphates (OPs) inhibit the enzyme cholinesterase and cause accumulation of acetylcholine, and are known to cause seizures and status epilepticus (SE) in humans. The animal models of SE caused by organophosphate analogs of insecticides are not well characterized. SE caused...
Iris Mangas et al.
Toxicology and applied pharmacology, 256(3), 360-368 (2011-05-24)
Some published studies suggest that low level exposure to organophosphorus esters (OPs) may cause neurological and neurobehavioral effects at long term exposure. These effects cannot be explained by action on known targets. In this work, the interactions (inhibition, spontaneous reactivation...

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