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ATMP

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For other uses, see ATMP (disambiguation).
ATMP
Names
Preferred IUPAC name tris(phosphonic acid)
Other names
  • Tris(phosphonomethyl)amine
  • Nitrilotrimethylphosphonic acid
  • Aminotris(methylphosphonic acid)
  • ATMP
  • NTMP
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.026.496 Edit this at Wikidata
EC Number
  • 229-146-5
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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)Key: YDONNITUKPKTIG-UHFFFAOYSA-N
  • 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)Key: YDONNITUKPKTIG-UHFFFAOYAN
SMILES
  • O=P(O)(O)CN(CP(=O)(O)O)CP(=O)(O)O
Properties
Chemical formula C3H12NO9P3
Molar mass 299.048 g·mol
Appearance White solid
Density 1.33 g/cm (20 °C)
Melting point 200 °C (392 °F; 473 K) decomposes
Solubility in water 61 g/100 mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 , 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.

Properties

ATMP has good antiscale performance. It is related structurally to nitrilotriacetic acid.

Applications

References

  1. Petrov, K. A.; Maklyaev, F. L.; Bliznyuk, N. K (1959). "Synthesis of aminodiphosphonates and aminotriphosphonates". Zhurnal Obshchei Khimii. 29: 591–4.
  2. Moedritzer, Kurt; Irani, Riyad R. (1966). "The Direct Synthesis of α-Aminomethylphosphonic Acids. Mannich-Type Reactions with Orthophosphorous Acid". The Journal of Organic Chemistry. 31 (5): 1603. doi:10.1021/jo01343a067.
  3. Labjar, Najoua; Lebrini, Mounim; Bentiss, Fouad; Chihib, Nour-Eddine; Hajjaji, Souad El; Jama, Charafeddine (2010). "Corrosion inhibition of carbon steel and antibacterial properties of aminotris-(methylenephosphonic) acid". Materials Chemistry and Physics. 119 (1–2): 330–336. doi:10.1016/j.matchemphys.2009.09.006.
  4. Tang, Yongming; Yang, Wenzhong; Yin, Xiaoshuang; Liu, Ying; Yin, Pengwei; Wang, Jintang (2008). "Investigation of CaCO3 scale inhibition by PAA, ATMP and PAPEMP". Desalination. 228 (1–3): 55–60. doi:10.1016/j.desal.2007.08.006.
  5. Cabeza, Aurelio; Ouyang, Xiang; Sharma, C. V. Krishnamohan; Aranda, Miguel A. G.; Bruque, Sebastian; Clearfield, Abraham (2002-05-01). "Complexes Formed between Nitrilotris(methylenephosphonic acid) and M 2+ Transition Metals: Isostructural Organic−Inorganic Hybrids". Inorganic Chemistry. 41 (9): 2325–2333. doi:10.1021/ic0110373. ISSN 0020-1669.
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