ATMP

ATMP
Names
	Preferred IUPAC name [Nitrilotris(methylene)]tris(phosphonic acid)
	Other names Tris(phosphonomethyl)amine; Nitrilotrimethylphosphonic acid; Aminotris(methylphosphonic acid); ATMP; NTMP;
Identifiers
CAS Number	6419-19-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL260191 ;
ChemSpider	15833 ;
ECHA InfoCard	100.026.496
EC Number	229-146-5;
PubChem CID	16698;
UNII	1Y702GD0FG ;
CompTox Dashboard (EPA)	DTXSID2027624 ;
	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−1
Appearance	White solid
Density	1.33 g/cm3 (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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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

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

Applications

Related compounds

(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

^ Petrov, K. A.; Maklyaev, F. L.; Bliznyuk, N. K (1959). "Synthesis of aminodiphosphonates and aminotriphosphonates". Zhurnal Obshchei Khimii. 29: 591–4.
^ 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.
^ 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.
^ 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.
^ 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.

[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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Names

Preferred IUPAC name [Nitrilotris(methylene)]tris(phosphonic acid)
Other names Tris(phosphonomethyl)amine Nitrilotrimethylphosphonic acid Aminotris(methylphosphonic acid) ATMP NTMP
Identifiers
CAS Number	6419-19-8^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL260191^Y
ChemSpider	15833^Y
ECHA InfoCard	100.026.496
EC Number	229-146-5
PubChem CID	16698
UNII	1Y702GD0FG^N
CompTox Dashboard (EPA)	DTXSID2027624
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)^Y Key: YDONNITUKPKTIG-UHFFFAOYSA-N^Y 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⁻¹
Appearance	White solid
Density	1.33 g/cm³ (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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references