Aminomethylphosphonic acid

Aminomethylphosphonic acid (AMPA) is a weak organic acid with a phosphonic acid group.

Aminomethylphosphonic acid
Names
Preferred IUPAC name
(Aminomethyl)phosphonic acid
Other names
Aminomethanephosphonic acid
Identifiers
3D model (JSmol)
AbbreviationsAMPA; AMeP
ChEBI
ChemSpider
ECHA InfoCard100.152.014 Edit this at Wikidata
UNII
  • InChI=1S/CH6NO3P/c2-1-6(3,4)5/h1-2H2,(H2,3,4,5)
    Key: MGRVRXRGTBOSHW-UHFFFAOYSA-N
  • InChI=1/CH6NO3P/c2-1-6(3,4)5/h1-2H2,(H2,3,4,5)
    Key: MGRVRXRGTBOSHW-UHFFFAOYAF
  • O=P(O)(O)CN
Properties
CH6NO3P
Molar mass111.037 g·mol−1
AppearanceSolid
Melting point338 to 344 °C (640 to 651 °F; 611 to 617 K)
Acidity (pKa)0.4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Application

AMPA apparently can be used as biocide and pesticide.[1] AMPA is also used in research to assess the exposure of glyphosate.[2]

Structures of AMPA in different pH ranges[3]

Environmental fate

AMPA is one of the primary degradation products of the herbicide glyphosate[4] and the related chemical glyphosat-trimesium.[1]

AMPA has the potential to be broken down further by manganese oxide in laboratory conditions, however in soil manganese oxide is usually only present in trace amounts.[5] Microbial degradation of AMPA is the more likely degradation pathway, where it degrades into phosphoric acid[6][7] and ultimately to carbon dioxide and inorganic phosphate.[8]

Toxicity

AMPA has toxicity which is comparable to that of glyphosate and it is therefore considered to be of similar toxicological concern (harmful in greater than 0.5 parts per million) as glyphosate itself.[9]

References