The World's Largest Producer of Squaric Acid Emerges: Watson Leads the Way

IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NamePropanoic acid, 2,2-dimethyl-, 1,1',1',1'''-] esterIUPAC Nameoxymethyl 2,2-dimethylpropanoateMolecular StructureCAS Registry Number 134606-34-1Synonyms134606-34-1Tetrakis methylenediphosphonateSCHEMBL2458617UNXRGZHZKHCCJB-UHFFFAOYSA-NE87254methylenebisphosphonic acid tetra(pivaloyloxymethyl) ester(METHYLENEBIS(PHOSPHORYL)TETRAKIS(OXY))TETRAKIS(METHYLENE) TETRAKIS(2,2-DIMETHYLPROPANOATE)oxymethyl 2,2-dimethylpropanoateMolecular FormulaC25H46O14P2 Molecular Weight632.6InChIInChI=1S/C25H46O14P2/c1-22(2,3)18(26)32-13-36-40(30,37-14-33-19(27)23(4,5)6)17-41(31,38-15-34-20(28)24(7,8)9)39-16-35-21(29)25(10,11)12/h13-17H2,1-12H3 InChI KeyUNXRGZHZKHCCJB-UHFFFAOYSA-NIsomeric SMILESCC(C)(C)C(=O)OCOP(=O)(CP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C

Physical Data

AppearanceWhite powder

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHzChemical shifts1Hchloroform-d1Chemical shifts1Hchloroform-d1400Chemical shifts1Hchloroform-d1500Chemical shifts31Pchloroform-d1500

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Propanoic acid, 2,2-dimethyl-, 1,1',1',1'''-] ester CAS 134606-34-1

ConditionsYieldWith potassium hydroxide In toluene at 40℃; for 8h;Experimental Procedurea.35 Preparation of compound 46-5:To a solution of 46-4 (3.3 g, 12.6 mmol) in toluene (30 mL) was added POM ester (7.9 g, 12.6 mmol) and KOH (1.3 g, 22.6 mmol) at room temperature. The reaction mixture was stirred at 40°C for 8 hours. LCMS showed 46-4 was consumed. The mixture was diluted with water and EA was added. The product was extracted with EA. The organic layer was washed with brine and dried over Na2SO4and concentrated to give the crude. The crude was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-1): Column, C18 silica gel; mobile phase, CH3CN/H2O (0.5% NH4HCO3) = 1/1 increasing to CH3CN/H2O (0.5% NH4HCO3) = 1/0 within 20 min, the eluted product was collected at CH3CN/H2O (0.5% NH4HCO3) = 91/9 Detector, UV 254 nm. This resulted in 46-5 (5.4 g, 9.5 mmol, 75.9% yield) as an oil. ESI-LCMS: m/z 567.2 +; 1H-NMR (400 MHz, CDCl3) δ 6.89-6.77(m, 1H), 6.07-5.96(m, 1H), 5.86-5.55(m, 4H), 4.85 -4.73(m, 1H), 4.36-4.27(m, 1H), 4.05-3.96(m, 1H), 3.95-3.85(m, 1H), 3.73-3.65(m, 1H), 3.44-3.35 (m, 3H), 1.30-1.25(s, 18H), 0.94-0.84(s, 9H), 0.14-0.05(s, 6H). 31P-NMR (162 MHz, CDCl3) δ 18.30, 15.11.75.9%

Safety and Hazards

No data available

Other Data

TransportationStorage at -20°,keep away from light and sealedHS CodeStorageStorage at -20°,keep away from light and sealedShelf Life1 yearMarket Price

DruglikenessLipinski rules componentMolecular Weight632.579logP2.534HBA14HBD0Matching Lipinski Rules2Veber rules componentPolar Surface Area (PSA)195.88Rotatable Bond (RotB)22Matching Veber Rules0

Use PatternPropanoic acid, 2,2-dimethyl-, 1,1',1',1'''-] ester CAS 134606-34-1 is used in IVD.
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