dimethyl [(trimethylsilyl)methyl]phosphonate

• ChemBase ID: 138136
• Molecular Formular: C6H17O3PSi
• Molecular Mass: 196.256641
• Monoisotopic Mass: 196.06845757
• SMILES: COP(=O)(C[Si](C)(C)C)OC
• Canonical SMILES: COP(=O)(C[Si](C)(C)C)OC
• InChI: InChI=1S/C6H17O3PSi/c1-8-10(7,9-2)6-11(3,4)5/h6H2,1-5H3
• InChIKey: QBHFBIHXALNDCB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl [(trimethylsilyl)methyl]phosphonate
• IUPAC Traditional name: dimethyl (trimethylsilyl)methylphosphonate
• Synonyms: [(Trimethylsilyl)methyl]-phosphonic acid dimethyl ester; Dimethyl trimethylsilylmethylphosphonate; 三甲硅基甲基膦酸二甲酯

Database IDs

• CAS Number: 13433-42-6
• MDL Number: MFCD00042921
• Beilstein Number: 2412153
• PubChem SID: 162232394; 24889711
• PubChem CID: 4305701

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.2125
• LogD (pH = 7.4): 2.2125
• Log P: 2.2125
• Molar Refractivity: 41.6377 cm^3
• Polarizability: 19.446962 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 111-114 °C/21.5 mmHg(lit.); 90-95°C/10mm
• Flash Point: 159.8 °F; 71 °C; 76°C(169°F)
• Density: 1.024; 1.024 g/mL at 25 °C(lit.)
• Refractive Index: 1.435; n20/D 1.435; n20/D 1.435(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H227; H315-H319-H335
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P403+P235-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥97.0%; 96%; 97%
• Linear Formula: (CH3)3SiCH2P(O)(OCH3)2

DETAILS

Sigma Aldrich - 92750

Other Notes
Reagent for the preparation of olefinic sugar phosphonates6; For the direct methylenation of carbonyl compounds7
Packaging
1 mL in glass bottle
Application
Reactant for:
• Synthesis of phosphonato-phosphine palladacycles1
• Studying the synthetic applications of phosphoryl-stabilized anions2
• Peterson olefination reactions3
• Dilithiation4,5 and transmetalation4

Sigma Aldrich - 375993

Application
Reactant for:
• Synthesis of phosphonato-phosphine palladacycles1
• Studying the synthetic applications of phosphoryl-stabilized anions2
• Peterson olefination reactions3
• Dilithiation4,5 and transmetalation4