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38399

Diisopropylfluorophosphate

≥97.0% (GC)

Synonym(s):

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

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About This Item

Linear Formula:
[(CH3)2CHO]2POF
CAS Number:
55-91-4
Molecular Weight:
184.15
EC Number:
200-247-6
UNSPSC Code:
12352200
PubChem Substance ID:
329755682
Beilstein/REAXYS Number:
1723307
MDL number:
MFCD00008873
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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)

Biochem/physiol Actions

Potent inhibitor of serine proteases and acetylcholinesterase; inhibits cathepsin G, cholinesterase, coagulation factor Xa, leucocyte elastase, pancreatic elastase, tissue kallikrein, plasmin, subtilisin, and thrombin. Inhibits apoptosis induced by ricin and bacterial toxins.
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
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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

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J.K. McDonald et al.
Methods in Enzymology, XV(B), 275-275 (1972)
J.A. Cohen et al.
Methods in Enzymology, XI, 686-686 (1967)
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
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