(phosphonomethyl)phosphonic acid

• ChemBase ID: 75000
• Molecular Formular: CH6O6P2
• Molecular Mass: 176.002262
• Monoisotopic Mass: 175.96396117
• SMILES: P(=O)(O)(O)CP(=O)(O)O
• Canonical SMILES: OP(=O)(CP(=O)(O)O)O
• InChI: InChI=1S/CH6O6P2/c2-8(3,4)1-9(5,6)7/h1H2,(H2,2,3,4)(H2,5,6,7)
• InChIKey: MBKDYNNUVRNNRF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (phosphonomethyl)phosphonic acid
• IUPAC Traditional name: methylene diphosphonate
• Synonyms: Methylenediphosphonic acid; Medronic acid; Methylenebisphosphonic acid; Methylenediphosphonic acid; Methylenebiphosphonic Acid; Methanebisphosphonic Acid; Bis(dihydroxyphosphoryl)methane; Methanediphosphonic acid; Methylenebis(phosphonic acid); Methylene diphosphonate; Medronate; Phosphonomethylphosphonic acid; MDP; Medronic acid; 亚甲磷酸; 亚甲基二膦酸

Database IDs

• CAS Number: 1984-15-2
• EC Number: 217-851-0
• MDL Number: MFCD00002139
• Beilstein Number: 1708494
• Merck Index: 145792
• PubChem SID: 24897338; 24883203; 162039918
• PubChem CID: 16124
• CHEMBL: 180570
• Chemspider ID: 15308
• KEGG ID: D04887
• Wikipedia Title: Medronic_acid

CALCULATED PROPERTIES

• Acid pKa: 1.2687747
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -6.939664
• LogD (pH = 7.4): -7.087618
• Log P: -2.3549147
• Molar Refractivity: 27.8785 cm^3
• Polarizability: 11.678405 Å^3
• Polar Surface Area: 115.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Crystalline; White Solid
• Melting Point: 186-188°C; 197-199 °C(lit.); 197-204°C; 199–200 °C; 201-205 °C; 202-204°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Corrosive/Harmful/Light Sensitive/Store at -20°C
• RTECS: SZ9138000
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3; III
• Risk Statements: 34
• Safety Statements: 20-26-36/37/39-45-60; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• LD50: 45-50 mg/kg (i.v., mice, rabbits)
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥99%; ≥99.0% (T); 97%; 98%; 99+%
• Impurities: <0.5% methyl alcohol; 1% ethyl alcohol
• Linear Formula: CH2[P(O)(OH)2]2

DETAILS

Sigma Aldrich - 64255

Other Notes
This isosteric compound of pyrophosphate is used for preparing analogues of natural di- and triphosphates1,2; 99mTc-complex is employed in nuclear medicine for scintigraphy3,4; used for caries, dental calculus and plaque inhibition.

Sigma Aldrich - M9508

包装
1, 5, 10 g in glass bottle
250 mg in glass bottle

Toronto Research Chemicals - M203500

Radioactive imaging agent.

REFERENCES

• Subramanian, G., et al.: J. Nucl. Med., 16, 744 (1975)
• Rosenthall, L., et al.: Clin. Nucl. Med., 2, 232 (1975)
• Bull, U., et al.: Br. J. Radiol., 50, 629 (1975)
• Garty, I., et al.: Clin. Nucl. Med., 14, 515 (1989)
• The Tc complex is used in bone scintigraphy.
• Used as an analogue of inorganic pyrophosphate for preparation of analogues of natural di- and tri-phosphates. See, e.g.: J. Org. Chem., 44, 3997 (1979). Review: Chem. Rev., 77, 872 (1977).