methyl 2-(dimethoxyphosphoryl)acetate

• ChemBase ID: 112025
• Molecular Formular: C5H11O5P
• Molecular Mass: 182.111601
• Monoisotopic Mass: 182.03441008
• SMILES: COC(=O)CP(=O)(OC)OC
• Canonical SMILES: COC(=O)CP(=O)(OC)OC
• InChI: InChI=1S/C5H11O5P/c1-8-5(6)4-11(7,9-2)10-3/h4H2,1-3H3
• InChIKey: SIGOIUCRXKUEIG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-(dimethoxyphosphoryl)acetate
• IUPAC Traditional name: methyl 2-(dimethoxyphosphoryl)acetate
• Synonyms: (Carboxymethyl)phosphonic acid trimethyl ester; NSC 84262; Trimethyl phosphonoacetate; TRIMETHYL PHOSPHONOACETATE; Dimethyl methoxycarbonylmethylphosphonate; Phosphonoacetic acid trimethyl ester; methyl 2-(dimethoxyphosphoryl)acetate; 三甲基膦酰基乙酸酯; 磷酸乙酸三甲酯

Database IDs

• CAS Number: 5927-18-4
• EC Number: 227-663-0
• MDL Number: MFCD00008452
• Beilstein Number: 1865177
• PubChem SID: 162097263; 24887467; 24900489
• PubChem CID: 80029

CALCULATED PROPERTIES

• Acid pKa: 18.555302
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.42275944
• LogD (pH = 7.4): -0.42275944
• Log P: -0.42275944
• Molar Refractivity: 37.3677 cm^3
• Polarizability: 15.617066 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 118 °C/0.85 mmHg(lit.); 119-120°C/1mm; 265-268 °C(lit.)
• Flash Point: 113 °C; 235.4 °F; 70°C(158°F)
• Density: 1.125 g/mL at 25 °C(lit.); 1.263
• Refractive Index: 1.4370; n20/D 1.437; n20/D 1.437(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 9-36
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335-H227
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥98.0% (GC); 98%
• Grade: purum
• Linear Formula: (CH3O)2P(O)CH2CO2CH3

DETAILS

MP Biomedicals - 05222246

MP Biomedicals Rare Chemical collection

Sigma Aldrich - T79758

Packaging
25, 100 g in glass bottle
Application
Reactant involved in:
• Intramolecular Mannich-type reactions to produce the sarain A diazatricyclic core1
• Organocatalytic oxa-Michael reactions2
• Prenylation and geranylation of oxindoles3
• Intramolecular Horner-Wadsworth-Emmons reactions4,5
• Olefin cross-metathesis / heterocyclization6

Sigma Aldrich - 79527

Application
Reactant involved in:
• Intramolecular Mannich-type reactions to produce the sarain A diazatricyclic core1
• Organocatalytic oxa-Michael reactions2
• Prenylation and geranylation of oxindoles3
• Intramolecular Horner-Wadsworth-Emmons reactions4,5
• Olefin cross-metathesis / heterocyclization6

REFERENCES

• Horner-Wadsworth-Emmons olefination (see Appendix 1) with aldehydes and ketones gives acrylic esters, cf Triethyl phosphonoacetate, A14120. In general, the (E):(Z) ratio of the resulting alkene increases as the counter-ion becomes smaller (K, Na, Li) and as the temperature increases. See, e.g.: J. Org. Chem., 55, 3386 (1990). Reaction with ɑ-hydroxy ketones provides a simple route to butenolides: Tetrahedron Lett., 36, 2839 (1995):