diisopropyl methylphosphonate

{{Distinguish|DIMP (antiandrogen)}}

{{Chembox

| ImageFile = Diisopropyl methylphosphonate-2D-by-AHRLS-2012.png

| ImageFile1 = DIMP-3D-balls-by-AHRLS-2012.png

| ImageFile_Ref = {{Chemboximage|correct|??}}

| ImageName = Diisopropyl methlyphosphonate chemical structure

| PIN = Di(propan-2-yl) methylphosphonate

| OtherNames = 2-(Methyl-propan-2-yloxyphosphoryl)oxypropane

|Section1={{Chembox Identifiers

| Abbreviations = DIMP

| CASNo = 1445-75-6

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 56V3OG5DC7

| PubChem = 3073

| ChEBI = 77325

| SMILES = CP(OC(C)C)(OC(C)C)=O

| ChemSpiderID = 2964

| InChI = 1/C7H17O3P/c1-6(2)9-11(5,8)10-7(3)4/h6-7H,1-5H3

| InChIKey = WOAFDHWYKSOANX-UHFFFAOYAE

| StdInChI = 1S/C7H17O3P/c1-6(2)9-11(5,8)10-7(3)4/h6-7H,1-5H3

| StdInChIKey = WOAFDHWYKSOANX-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=7 | H=17 | O=3 | P=1

| Appearance =

| Density = 0.976 g/mL

| MeltingPt =

| BoilingPtC = 215

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPtC = 98

| AutoignitionPtC = }}

}}

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.{{cite web|url=https://wwwn.cdc.gov/TSP/substances/ToxSubstance.aspx?toxid=203 |title=ATSDR - Toxic Substances - Diisopropyl Methylphosphonate (DIMP) |publisher=Atsdr.cdc.gov }}

DIMP is a colorless liquid that has been shown to affect the hematological (blood forming) system in animals.{{cite web|url=http://www.atsdr.cdc.gov/toxfaqs/tfacts119.pdf |title=diisopropyl methylphosphonate datasheet |publisher=ATSDR |id=tf119 |date=August 1999 |access-date=2012-10-18}} Its chemical formula is {{chem2|C7H17O3P}}.{{cite web|url=http://www.chemicals.pl/ |title=Center of Chemicals|publisher=Chemicals.pl |date= |access-date=2012-10-18}}

It degrades into isopropyl methylphosphonic acid.

History

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

Use

No commercial uses of DIMP are known to exist.{{cite report |chapter-url=http://www.atsdr.cdc.gov/toxprofiles/tp119-c4.pdf |title=TOXICOLOGICAL PROFILE FOR DIISOPROPYL METHYLPHOSPHONATE |date=August 1998 |chapter=4.3 USE |page=92 |publisher=ATSDR}}

Occurrences

DIMP is not known to occur naturally in the environment.{{fact|date=January 2023}}

Productions

=Synthesis=

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

References