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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:
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

replaced by

Product No.
Description
Pricing

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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

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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)
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 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)
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
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