Diisopropyl methylphosphonate

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Diisopropyl methylphosphonate
Diisopropyl methylphosphonate-2D-by-AHRLS-2012.png
DIMP-3D-balls-by-AHRLS-2012.png
Names
Preferred IUPAC name
Di(propan-2-yl) methylphosphonate
Other names
2-(Methyl-propan-2-yloxyphosphoryl)oxypropane
Identifiers
3D model (JSmol)
AbbreviationsDIMP
ChEBI
ChemSpider
ECHA InfoCard 100.014.451 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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]

Contents

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.

Related Research Articles

Nerve agents, sometimes also called nerve gases, are a class of organic chemicals that disrupt the mechanisms by which nerves transfer messages to organs. The disruption is caused by the blocking of acetylcholinesterase (AChE), an enzyme that catalyzes the breakdown of acetylcholine, a neurotransmitter. Nerve agents are irreversible acetylcholinesterase inhibitors used as poison.

<span class="mw-page-title-main">Sarin</span> Chemical compound and chemical warfare nerve agent

Sarin is an extremely toxic organophosphorus compound. A colourless, odourless liquid, it is used as a chemical weapon due to its extreme potency as a nerve agent. Exposure can be lethal even at very low concentrations, where death can occur within one to ten minutes after direct inhalation of a lethal dose, due to suffocation from respiratory paralysis, unless antidotes are quickly administered. People who absorb a non-lethal dose and do not receive immediate medical treatment may suffer permanent neurological damage.

<span class="mw-page-title-main">Tabun (nerve agent)</span> Chemical compound

Tabun is an extremely toxic compound of the organophosphate family. It is not present in nature. At room temperature, the pure compound is a clear and viscous liquid. However, impurities imparted during its manufacture are almost always present, turning it into a yellow or brown liquid. Exposed to environs, it slowly volatizes into the atmosphere, with the vapor having a slight fruity or almond-like odor. As the compound has a much higher molecular mass compared to air, Tabun gas tends to accumulate in low-lying areas.

<span class="mw-page-title-main">Soman</span> Chemical compound (nerve agent)

Soman is an extremely toxic chemical substance. It is a nerve agent, interfering with normal functioning of the mammalian nervous system by inhibiting the enzyme cholinesterase. It is an inhibitor of both acetylcholinesterase and butyrylcholinesterase. As a chemical weapon, it is classified as a weapon of mass destruction by the United Nations according to UN Resolution 687. Its production is strictly controlled, and stockpiling is outlawed by the Chemical Weapons Convention of 1993 where it is classified as a Schedule 1 substance. Soman was the third of the so-called G-series nerve agents to be discovered along with GA (tabun), GB (sarin), and GF (cyclosarin).

<span class="mw-page-title-main">Denatured alcohol</span> Ethanol with additives to discourage recreational consumption

Denatured alcohol, also known as methylated spirits, metho, or meths in Australia, Ireland, New Zealand, South Africa, and the United Kingdom, and as denatured rectified spirit, is ethanol that has additives to make it poisonous, bad-tasting, foul-smelling, or nauseating to discourage its recreational consumption. It is sometimes dyed so that it can be identified visually. Pyridine and methanol, each and together, make denatured alcohol poisonous; and denatonium makes it bitter.

<span class="mw-page-title-main">VX (nerve agent)</span> Chemical compound and chemical warfare nerve agent

VX is an extremely toxic synthetic chemical compound in the organophosphorus class, specifically, a thiophosphonate. In the class of nerve agents, it was developed for military use in chemical warfare after translation of earlier discoveries of organophosphate toxicity in pesticide research. In its pure form, VX is an oily, relatively non-volatile liquid that is amber-like in colour. Because of its low volatility, VX persists in environments where it is dispersed.

<span class="mw-page-title-main">Rubbing alcohol</span> Alcohol used for germ protection

Rubbing alcohol, also known as surgical spirit in some regions, refers to a group of denatured alcohols commonly used as topical antiseptics. These solutions are primarily composed of either isopropyl alcohol (isopropanol) or ethanol, with isopropyl alcohol being the more widely available formulation. Rubbing alcohol is rendered undrinkable by the addition of bitterants or other denaturants.

Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, sweet-smelling, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant. Most chloromethane is biogenic.

<span class="mw-page-title-main">Agency for Toxic Substances and Disease Registry</span> US federal agency

The Agency for Toxic Substances and Disease Registry (ATSDR) is a federal public health agency within the United States Department of Health and Human Services' Centers for Disease Control and Prevention. The agency focuses on minimizing human health risks associated with exposure to hazardous substances. It works closely with other federal, state, and local agencies; tribal governments; local communities; and healthcare providers. Its mission is to "Serve the public through responsive public health actions to promote healthy and safe environments and prevent harmful exposures." ATSDR was created as an advisory, nonregulatory agency by the Superfund legislation and was formally organized in 1985.

<span class="mw-page-title-main">Chlorosarin</span> Chemical compound

Chlorosarin is a chemical precursor used in the final step of one method for the production of the nerve agent sarin. Also known as O-isopropyl methylphosphonochloridate and isopropyl methylphosphonic chloride, it has a molecular weight of 156.55 g/mol and a molecular formula of C4H10ClO2P.

<span class="mw-page-title-main">Diisopropyl ether</span> Chemical compound

Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. Diisopropyl ether is sometimes represented by the abbreviation DIPE.

Chemical, biological (CB) — and sometimes radiological — warfare agents were assigned what is termed a military symbol by the U.S. military until the American chemical and biological weapons programs were terminated. Military symbols applied to the CB agent fill, and not to the entire weapon. A chemical or biological weapon designation would be, for example, "Aero-14/B", which could be filled with GB, VX, TGB, or with a biological modification kit – OU, NU, UL, etc. A CB weapon is an integrated device of (1) agent, (2) dissemination means, and (3) delivery system.

<span class="mw-page-title-main">Dimethyl methylphosphonate</span> Chemical compound

Dimethyl methylphosphonate is an organophosphorus compound with the chemical formula CH3PO(OCH3)2. It is a colourless liquid, which is primarily used as a flame retardant.

<span class="mw-page-title-main">Diisopropyl fluorophosphate</span> Chemical compound

Diisopropyl fluorophosphate (DFP) or Isoflurophate is an oily, colorless liquid with the chemical formula C6H14FO3P. It is used in medicine and as an organophosphorus insecticide. It is stable, but undergoes hydrolysis when subjected to moisture.

Methylphosphonyl difluoride (DF), also known as EA-1251 or difluoro, is a chemical weapon precursor. Its chemical formula is CH3POF2. It is a Schedule 1 substance under the Chemical Weapons Convention. It is used for production of sarin and soman as a component of binary chemical weapons; an example is the M687 artillery shell, where it is used together with a mixture of isopropyl alcohol and isopropyl amine, producing sarin.

<span class="mw-page-title-main">1,3-Dichloropropene</span> Chemical compound

1,3-Dichloropropene, sold under diverse trade names, is an organochlorine compound with the formula C3H4Cl2. It is a colorless liquid with a sweet smell. It is feebly soluble in water and evaporates easily. It is used mainly in farming as a pesticide, specifically as a preplant fumigant and nematicide. It is widely used in the US and other countries, but is banned in 34 countries.

Isopropyl alcohol is a colorless, flammable, organic compound with a pungent alcoholic odor.

<span class="mw-page-title-main">4-Methylcyclohexanemethanol</span> Chemical compound

4-Methylcyclohexanemethanol (MCHM, systematic name 4-methylcyclohexylmethanol) is an organic compound with the formula CH3C6H10CH2OH. Classified as a saturated higher alicyclic primary alcohol. Both cis and trans isomers exist, depending on the relative positions of the methyl (CH3) and hydroxymethyl (CH2OH) groups on the cyclohexane ring. Commercial samples of MCHM consists of a mixture of these isomers as well as other components that vary with the supplier.

<span class="mw-page-title-main">3,3,5-Trimethylcyclohexyl 3-pyridyl methylphosphonate</span> Chemical compound

VP, also known as EA-1511, is an extremely toxic organophosphate nerve agent of the V-series.

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. [ bare URL PDF ]