Diisopropyl methylphosphonate

Not to be confused with DIMP (antiandrogen).
Diisopropyl methylphosphonate
Diisopropyl methlyphosphonate chemical structure
Names
Preferred IUPAC name
Di(propan-2-yl) methylphosphonate
Other names
2-(Methyl-propan-2-yloxyphosphoryl)oxypropane
Identifiers
3D model (JSmol)
Abbreviations DIMP
ChEBI
ChemSpider
ECHA InfoCard 100.014.451 Edit this at Wikidata
UNII
  • InChI=1S/C7H17O3P/c1-6(2)9-11(5,8)10-7(3)4/h6-7H,1-5H3
    Key: WOAFDHWYKSOANX-UHFFFAOYSA-N
  • InChI=1/C7H17O3P/c1-6(2)9-11(5,8)10-7(3)4/h6-7H,1-5H3
    Key: WOAFDHWYKSOANX-UHFFFAOYAE
  • CP(OC(C)C)(OC(C)C)=O
Properties
C7H17O3P
Molar mass 180.184 g·mol−1
Density 0.976 g/mL
Boiling point 215 °C (419 °F; 488 K)
Hazards
Flash point 98 °C (208 °F; 371 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diisopropyl methylphosphonate (DIMP), also known as diisopropyl methane-phosphonate and phosphonic acid and methyl-bis-(1-methylethyl)ester, is a chemical by-product in the production of sarin gas when two equivalents of isopropyl alcohol react with methylphosphonyl difluoride instead of one.[1]

DIMP is a colorless liquid that has been shown to affect the hematological (blood forming) system in animals.[2] Its chemical formula is C7H17O3P.[3]

It degrades into isopropyl methylphosphonic acid.[4]

History

DIMP is a chemical by-product resulted from the manufacture of sarin (GB).[5]

Use

No commercial uses of DIMP are known to exist.[6]

Occurrences

DIMP is not known to occur naturally in the environment.[citation needed]

Productions

Synthesis

DIMP can be prepared by a gradual addition of triisopropyl phosphite with methyl iodide, utilizing distillation technique.

References

  1. ^ "ATSDR - Toxic Substances - Diisopropyl Methylphosphonate (DIMP)". Atsdr.cdc.gov. 2011-03-03. Retrieved 2012-10-18.
  2. ^ "tf119" (PDF). Retrieved 2012-10-18.
  3. ^ "Center of Chemicals". Chemicals.pl. Retrieved 2012-10-18.
  4. ^ "Toxic Substances Portal – Diisopropyl Methylphosphonate (DIMP)". Agency for Toxic Substances and Disease Registry.
  5. ^ ATSDR – Toxic Substances – Diisopropyl Methylphosphonate (DIMP)
  6. ^ [1] [bare URL PDF]