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38399

Sigma-Aldrich

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
Beilstein/REAXYS Number:
1723307
EC Number:
200-247-6
MDL number:
MFCD00008873
UNSPSC Code:
12352200
PubChem Substance ID:
329755682

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

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Description
Pricing

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

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Certificates of Analysis (COA)

Lot/Batch Number
1404328
1364933
1352956
454142/1
439826/1

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J.K. McDonald et al.
Methods in Enzymology, XV(B), 275-275 (1972)
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
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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