:ATMP

{{Other uses}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477236771

| ImageFile = ATMP.png

| PIN = [Nitrilotris(methylene)]tris(phosphonic acid)

| OtherNames = {{Unbulleted list

| Tris(phosphonomethyl)amine

| Nitrilotrimethylphosphonic acid

| Aminotris(methylphosphonic acid)

| ATMP

| NTMP

}}

|Section1={{Chembox Identifiers

| 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)

| InChIKey = YDONNITUKPKTIG-UHFFFAOYAN

| PubChem = 16698

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 260191

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = YDONNITUKPKTIG-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 6419-19-8

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 1Y702GD0FG

| EC_number = 229-146-5

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 15833

| SMILES = O=P(O)(O)CN(CP(=O)(O)O)CP(=O)(O)O

}}

|Section2={{Chembox Properties

| C=3 | H=12 | N=1 | O=9 | P=3

| Appearance = White solid

| Density = 1.33 g/cm³ (20 °C)

| MeltingPtC = 200

| MeltingPt_notes = decomposes

| Solubility = 61 g/100 mL

}}

|Section7={{Chembox Hazards

| FlashPt =

}}

}}

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.{{cite journal|title=Synthesis of aminodiphosphonates and aminotriphosphonates|journal=Zhurnal Obshchei Khimii|volume=29|pages= 591–4|year=1959|last1=Petrov|first1=K. A.|last2=Maklyaev|first2=F. L.|last3=Bliznyuk|first3=N. K}}{{cite journal | doi = 10.1021/jo01343a067 | title = The Direct Synthesis of α-Aminomethylphosphonic Acids. Mannich-Type Reactions with Orthophosphorous Acid | year = 1966 | last1 = Moedritzer | first1 = Kurt | last2 = Irani | first2 = Riyad R. | journal = The Journal of Organic Chemistry | volume = 31 | issue = 5 | pages = 1603}}