diethyl methylphosphonate

• ChemBase ID: 74936
• Molecular Formular: C5H13O3P
• Molecular Mass: 152.128681
• Monoisotopic Mass: 152.06023091
• SMILES: P(=O)(OCC)(OCC)C
• Canonical SMILES: CCOP(=O)(OCC)C
• InChI: InChI=1S/C5H13O3P/c1-4-7-9(3,6)8-5-2/h4-5H2,1-3H3
• InChIKey: NYYLZXREFNYPKB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl methylphosphonate
• IUPAC Traditional name: diethyl methylphosphonate
• Synonyms: Diethylmethylphosphonate; DEMP; Diethoxymethylphosphine oxide; Bis(diethoxyphosphinyl)methane; Diethyl methylphosphonate; Diethyl methanephosphonate; Methylphosphonic acid diethyl ester; Diethyl methylphosphonate; 双(二乙氧基氧膦基)甲烷; 甲基膦酸二乙酯; 甲基磷酸二乙酯

Database IDs

• CAS Number: 683-08-9
• EC Number: 211-667-4
• MDL Number: MFCD00009813
• Beilstein Number: 1753416
• PubChem SID: 24883208; 162039854; 24856263
• PubChem CID: 12685

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.58740515
• LogD (pH = 7.4): 0.58740515
• Log P: 0.58740515
• Molar Refractivity: 35.6398 cm^3
• Polarizability: 14.680639 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 194 °C(lit.); 194°C
• Flash Point: 167 °F; 75 °C; 75°C(167°F)
• Density: 1.040; 1.041 g/mL at 25 °C(lit.)
• Refractive Index: 1.4140; n20/D 1.414; n20/D 1.414(lit.)

Safety Information

• RTECS: SZ9085000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H227
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-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% (GC); 95+%; 97%
• Grade: purum
• Linear Formula: CH3P(O)(OC2H5)2

DETAILS

Sigma Aldrich - 268119

Packaging
5, 25 g in glass bottle
Application
Reactant for the synthesis of:
• Fluoroalkyl α- and β-aminophosphonates1
• Acyclic nucleoside phosphonates with branched phosphonoethoxy-Et chains as potential antivirals2
• Difluoromethyl arylphosphonates3
• Pyridone alkaloids with neuritogenic activity4
• Lipophilic meropenem-derived prodrugs5
• Phomactin cyclohexane core and diterpenoid framework6
• Phosphonylated peptides via solid-phase synthesis7
Reagent employed in the synthesis of α-alkenyl, γ-hydroxyl, and dialkyl fluoroalkynyl phosphonates.

Sigma Aldrich - 64261

Application
Reactant for the synthesis of:
• Fluoroalkyl α- and β-aminophosphonates1
• Acyclic nucleoside phosphonates with branched phosphonoethoxy-Et chains as potential antivirals2
• Difluoromethyl arylphosphonates3
• Pyridone alkaloids with neuritogenic activity4
• Lipophilic meropenem-derived prodrugs5
• Phomactin cyclohexane core and diterpenoid framework6
• Phosphonylated peptides via solid-phase synthesis7

REFERENCES

• For synthetic applications of the lithio-derivatives of esters of methanephosphonic acid, see Dimethyl methylphosphonate, A14268.
• Dialkylation has been used in the synthesis of cyclobutanephosphonates which are intermediates in the synthesis of 3-phosphonocyclobutyl amino acids: J. Chem. Soc., Perkin 1, 493 (1997).
• Reaction of the lithio-derivative with dialkyl cyanamides gives, instead of the expected 2-phosphorylacetamide, a rearranged N-phosphorylated amidine: Chem. Commun., 609 (1998):