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Sigma-Aldrich

Nitrilotri(methylphosphonic acid)

≥95% (T)

Synonym(s):

ATMP, Aminotris(methylenephosphonic acid), [Bis(phosphonomethyl)amino]methylphosphonic acid

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About This Item

Linear Formula:
N[CH2PO(OH)2]3
CAS Number:
6419-19-8
Molecular Weight:
299.05
Beilstein:
1715724
EC Number:
229-146-5
MDL number:
MFCD00002138
UNSPSC Code:
12352100
PubChem Substance ID:
57652427
NACRES:
NA.22

Quality Level

100

Assay

≥95% (T)

form

crystals

mp

~215 °C (dec.)

SMILES string

OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O

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)

InChI key

YDONNITUKPKTIG-UHFFFAOYSA-N

Application

Nitrilotri(methylphosphonic acid) is a common chelating agent used in synthetic chemistry. Some of the other applications include:
  • Preparation of hexagonal porous three-dimensional structures encapsulating a template, layered structures with intercalated templates or linear polymers.
  • Synthesis of metal-organic frameworks in combination with uranyl nitrate.
  • Preparation of ingredient of anticorrosive protective coatings on the steel surface.
  • ATMP can also be employed as a scale inhibitor during squeeze treatments in oilfield operations.

Other Notes

Powerful complexing agent

Pictograms

Corrosion
GHS05

Signal Word

Warning

Hazard Statements

H290

Precautionary Statements

P234 - P390

Hazard Classifications

Met. Corr. 1

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Study of Ca? ATMP Precipitation in the Presence of Magnesium Ion.
Tantayakom V, et al.
Langmuir, 20(6), 2220-2226 (2004)
Three-dimensional hexagonal structures from a novel self-complementary molecular building block.
Krishnamohan Sharma CV and Clearfield A
Journal of the American Chemical Society, 122(18), 4394-4402 (2000)
Metal-organic frameworks based on uranyl and phosphonate ligands.
Monteiro B, et al.
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 70(1), 28-36 (2014)
Matthias Zehnder et al.
Journal of endodontics, 31(11), 817-820 (2005-10-27)
The aim of this study was to assess interactions of EDTA and citric acid (CA) with sodium hypochlorite (NaOCl), the indispensable endodontic irrigant. Other chelators were simultaneously evaluated as possible alternatives: sodium triphosphate (STP), amino tris methylenephosphonic acid (ATMA), and
Tuomas Lönnberg et al.
Nucleic acids symposium series (2004), (51)(51), 195-196 (2007-11-22)
To improve the recruitment of the catalytically active Ce(IV) ion to the DNA cleavage site in the ARCUT (Artificial Restriction DNA Cutter) system, two phosphonate ligands, nitrilotris(methylenephosphonic acid) (NTP) and N,N,N',N'-ethylenediaminetetra-(methylenephosphonic acid) (EDTP), have been linked to the 5'- or
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