{[bis(phosphonomethyl)amino]methyl}phosphonic acid

• ChemBase ID: 125976
• Molecular Formular: C3H12NO9P3
• Molecular Mass: 299.049963
• Monoisotopic Mass: 298.97249086
• SMILES: O=P(O)(O)CN(CP(=O)(O)O)CP(=O)(O)O
• Canonical SMILES: OP(=O)(CN(CP(=O)(O)O)CP(=O)(O)O)O
• 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)
• InChIKey: YDONNITUKPKTIG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[bis(phosphonomethyl)amino]methyl}phosphonic acid
• IUPAC Traditional name: ATMP
• Synonyms: Nitrilotri(methylphosphonic acid); Nitrilotri(methylphosphonic acid) solution; Nitrilotris(methylene)triphosphonic acid solution; Tris(phosphonomethyl)amine; Nitrilotrimethylphosphonic acid; Aminotris(methylphosphonic acid); ATMP; NTMP; ATMP; (Nitrilotris(methylene))triphosphonic acid; P,P’,P’’-[nitrilotris(methylene)]trisphosphonic Acid; 1,1,1-Nitrilotris(methylphosphonic Acid); Aminotri(methylenephosphonic Acid); Briquest 301; NTPH; Nitrilo-N,N,N-trimethylenephosphonic Acid; Sequion 20H45; Sequion OA; WSI 3310; Nitrilotris(methylene)triphosphonic Acid; 次氮基三亚甲基膦酸; 次氮基三亚甲基膦酸 溶液; 次氮基三(亚甲基)三膦酸 溶液

Database IDs

• CAS Number: 6419-19-8
• EC Number: 229-146-5
• MDL Number: MFCD00002138
• Beilstein Number: 1715724
• PubChem SID: 24848684; 162220319; 24886424
• PubChem CID: 16698
• CHEMBL: 260191
• Chemspider ID: 15833
• Wikipedia Title: ATMP

CALCULATED PROPERTIES

• Acid pKa: 1.080073
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -10.0215435
• LogD (pH = 7.4): -10.292768
• Log P: -3.130288
• Molar Refractivity: 51.7182 cm^3
• Polarizability: 21.294771 Å^3
• Polar Surface Area: 175.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 61 g/100 mL in water; Water
• Apperance: White solid; White Solid
• Melting Point: ~215 °C (dec.); 200 °C decomp.; 204-208°C
• Density: 1.3 g/mL at 25 °C; 1.33 g/cm^3 (20 °C)
• pH: 0.46

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• RTECS: SZ9860000
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 3265
• German water hazard class: 1
• Hazard Class: 8
• Packing Group: 3
• Risk Statements: 35; 36
• Safety Statements: 26; 26-36/37/39-45
• EU Index: not listed
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H314; H319
• GHS Precautionary statements: P280-P305 + P351 + P338-P310; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 3

Product Information

• Purity: ≥97.0% (T); 95+%
• Concentration: 50 wt. % in H2O
• Impurities: 10-20% aqueous inorganic acids
• Linear Formula: N[CH2P(O)(OH)2]3; N[CH2PO(OH)2]3

DETAILS

Sigma Aldrich - 144797

Packaging
1 kg in glass bottle
100 g in glass bottle

Sigma Aldrich - 72568

Other Notes
Powerful complexing agent1
Packaging
10, 50 g in glass bottle

Toronto Research Chemicals - N490200

A powerful complexing agent. A potent acid sphingomyelinase inhibitor.

REFERENCES

• Marathe, S., et al.: J. Biol. Chem., 273, 4081 (1998)
• Lang, P., et al.: Nat. Med., 13, 164 (1998)
• Nara, F., et al.: J. Antibiot., 52, 525 (1998)
• Szajnman, S., et al.: Bioorg. Med. Chem. Lett., 15, 4685 (1998)