ATMP

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For other uses, see ATMP (disambiguation).
ATMP
Names
Preferred IUPAC name
[Nitrilotris(methylene)]tris(phosphonic acid)
Other names
  • Tris(phosphonomethyl)amine
  • Nitrilotrimethylphosphonic acid
  • Aminotris(methylphosphonic acid)
  • ATMP
  • NTMP
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
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EC Number
  • 229-146-5
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UNII
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  • InChI=1S/C3H12NO9P3/c5-14(6,7)1-4(2-15(8,9)10)3-16(11,12)13/h1-3H2,(H2,5,6,7)(H2,8,9,10)(H2,11,12,13) checkY
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  • InChI=1/C3H12NO9P3/c5-14(6,7)1-4(2-15(8,9)10)3-16(11,12)13/h1-3H2,(H2,5,6,7)(H2,8,9,10)(H2,11,12,13)
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  • O=P(O)(O)CN(CP(=O)(O)O)CP(=O)(O)O
Properties
C3H12NO9P3
Molar mass 299.048 g·mol−1
Appearance White solid
Density 1.33 g/cm3 (20 °C)
Melting point 200 °C (392 °F; 473 K) decomposes
61 g/100 mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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ATMP or aminotris(methylenephosphonic acid) is a phosphonic acid with chemical formula N(CH2PO3H2)3. It is a colorless solid. Its conjugate bases, such as [N(CH2PO3H)3]3-, have chelating properties.

ATMP can be synthesized from the Mannich-type reaction of ammonia, formaldehyde, and phosphorous acid, in a manner similar to the Kabachnik–Fields reaction.[1][2]

Properties

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ATMP has good antiscale performance.[3][4] It is related structurally to nitrilotriacetic acid.[5]

Applications

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  • (1-Aminoethylidene)bisphosphonic acid, CH3C(NH2)[PO(OH)2]2, also a chelating agent
  • Etidronic acid, CH3C(OH)[PO(OH)2]2, also a chelating agent
  • Glyphosate, HO2CCH2NHCH2[PO(OH)2]2, a herbicide

References

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