bis(propan-2-yl) fluorophosphonate

• ChemBase ID: 559
• Molecular Formular: C6H14FO3P
• Molecular Mass: 184.1457242
• Monoisotopic Mass: 184.06645916
• SMILES: P(=O)(F)(OC(C)C)OC(C)C
• Canonical SMILES: CC(OP(=O)(OC(C)C)F)C
• InChI: InChI=1S/C6H14FO3P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3
• InChIKey: MUCZHBLJLSDCSD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(propan-2-yl) fluorophosphonate
• IUPAC Traditional name: isoflurophate
• Brand Name: Diisopropyl Fluoridophosphate; Diisopropyl Fluorophosphate; Diisopropyl Fluorophosphonate; Diisopropyl Phosphofluoridate; Diisopropyl Phosphorofluoridate; Diisopropylfluorfosfat; Disiopropyl Fluorophosphonate; Dyflos; Floropryl; Fluorodiisopropyl Phosphate; Fluoropryl; Fluostigmine; Fluropryl; Humorsol; Isofluorophate; Isofluorphate; Isoflurophosphate; Isopropyl Fluophosphate; Isopropyl Phosphorofluoridate; Neoglaucit; O,O-Diisopropyl Fluorophosphate; PF-3
• Synonyms: DFP; Diflupyl; Diflurophate; Diisopropoxyphosphoryl Fluoride; Isoflurophate; DIFP; Diisopropylfluorophosphate; Diisopropyl fluorophosphate; Phosphorofluoridic Acid Bis(1-methylethyl) Ester; Phosphorofluoridic Acid Diisopropyl Ester; Dyflos; Floropryl; Fluorodiisopropyl phosphate; Fluostigmine; Isoflurophate; Isopropyl Fluophosphate; Diisopropyl phosphorofluoridate; Phosphoric acid diisopropyl ester fluoride; 二异丙基氟磷酸酯; 氟代磷酸二异丙酯; 氟磷酸二异丙酯

Database IDs

• CAS Number: 55-91-4
• EC Number: 200-247-6
• MDL Number: MFCD00008873
• Beilstein Number: 1723307
• PubChem SID: 46504499; 160964022; 24863641; 24893303
• PubChem CID: 5936
• CHEBI ID: 17941
• ATC CODE: S01EB07
• CHEMBL: 1025
• Chemspider ID: 5723
• DrugBank ID: DB00677
• KEGG ID: D00043
• Unique Ingredient Identifier: 12UHW9R67N
• Wikipedia Title: Diisopropyl_fluorophosphate

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.7603906
• LogD (pH = 7.4): 1.7603906
• Log P: 1.7603906
• Molar Refractivity: 40.888 cm^3
• Polarizability: 16.348886 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.1
• LOG S: -1.43
• Solubility (Water): 6.78e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1.54E+004 mg/L; Acetone; anhydrous isopropanol: soluble0.1-0.5 M (stable for months if stored at -70 °C); Benzene; H2O: soluble1.5% at 25 °C (very unstable (at pH 7.5, half-life = 1 hr); decomposed by alkali.)
• Apperance: Colourless Liquid
• Melting Point: -82 °C(lit.); -82°C (-115.6°F)
• Boiling Point: 183°C (361.4°F) (1013 mbar); 46°C/5mm; 62 °C/9 mmHg(lit.)
• Density: 1.06 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.385(lit.)
• Vapor Pressure: 0.58 mmHg ( 20 °C)
• Hydrophobicity(logP): 1.4

Safety Information

• Storage Condition: Refrigerator
• RTECS: TE5075000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3382
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300 +H310 + H330
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3382 6.1/PG 1
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... PTGS1(5742), PTGS2(5743)

Product Information

• Purity: ≥97.0% (GC)
• Linear Formula: [(CH3)2CHO]2POF

DETAILS

DrugBank - DB00677

• Drug Groups: approved
• Description: An irreversible cholinesterase inhibitor with actions similar to those of echothiophate. It is a powerful miotic used mainly in the treatment of glaucoma. Its vapor is highly toxic and it is recommended that only solutions in arachis oil be used therapeutically. (From Martindale, The Extra Pharmacopoeia, 29th ed, p1330)
• Indication: For use in the eye to treat certain types of glaucoma and other eye conditions, such as accommodative esotropia.
• Pharmacology: Isoflurophate is used as ocular drops in the treatment of chronic glaucoma. Isoflurophate is an organophosphorus compound that acts as an irreversible cholinesterase inhibitor. As such, it displays parasympathomimetic effects. Isoflurophate is used in the eye to treat certain types of glaucoma and other eye conditions, such as accommodative esotropia. They may also be used in the diagnosis of certain eye conditions, such as accommodative esotropia. Isoflurophate damages the acetylcholinesterase enzyme and is therefore irreversible, however, pralidoxime can displace organophosphates such as isoflurophate from acetylcholinesterase, but only if administered before isoflurophate damages (alkylates) the enzyme.
• Toxicity: Signs of overdose include increased sweating, loss of bladder control, muscle weakness, nausea, vomiting, diarrhea, or stomach cramps or pain, shortness of breath, tightness in chest, or wheezing, slow or irregular heartbeat, unusual tiredness or weakness, watering of mouth.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia

Sigma Aldrich - D0879

Analysis Note
使用浓度通常为 0.10mM。苯甲基磺酰氟 (PMSF) 是一种更安全的丝氨酸蛋白酶替代抑制剂。
Other Notes
Stored properly at 2-8°C, in an unopened bottle, DIFP should be stable for a minimum of two years. DIFPis unstable when exposed to moisture. DIFP will develop a dark yellow color upon decomposition.
Biochem/physiol Actions
丝氨酸蛋白酶（如胰蛋白酶和胰凝乳蛋白酶）和乙酰胆碱酯酶的强效抑制剂；还抑制组织蛋白酶 G、胆碱脂酶、凝血因子 Xa、白细胞弹性蛋白酶、胰弹性蛋白酶、组织激肽释放酶、血纤维蛋白熔酶、枯草杆菌蛋白酶以及凝血酶。乙酰胆碱酯酶的抑制作用使该化合物具有特别强的毒性。抑制由篦麻毒素和细菌毒素诱导的细胞凋亡。

Sigma Aldrich - D126004

Analysis Note
Typically used at a concentration of 0.10 mM. A safer alternative inhibitor for serine protease is phenylmethylsulfonyl fluoride (PMSF).
Application
Potent acetylcholinesterase inhibitor.1,2
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.

Sigma Aldrich - 38399

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)1; Inhibition of carboxypeptidase but not DAP I2
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.

Toronto Research Chemicals - D455300

A potent inhibitor of serine proteases such as trypsin and chymotrypsin, and of acetylcholinesterase.

REFERENCES

• Sarin, A., et al.: J. Exp. Med., 178, 1693 (1993)
• Takahashi, M., et al.: Mol. Reprod. Dev., 38, 310 (1994)