CAS 683-08-9|diethyl methylphosphonate|Diethylmethylphosphonate|diethyl methylphosphonate|双(二乙氧基氧膦基)甲烷|甲基膦酸二乙酯|Diethyl methylphosphonate|Diethoxymethylphosphine oxide|DEMP|Bis(dieth...

General Information

Structure

Molecular Formula

C₅H₁₃O₃P

Molecular Mass

152.128681

Exact Mass

152.06023091

Charge

InChI

InChI=1S/C5H13O3P/c1-4-7-9(3,6)8-5-2/h4-5H2,1-3H3

InChIKey

NYYLZXREFNYPKB-UHFFFAOYSA-N

Canonic Smiles

CCOP(=O)(OCC)C

Isomeric Smiles

P(=O)(OCC)(OCC)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

0.58740515

LogD (pH = 7.4)

0.58740515

Log P

0.58740515

Molar Refractivity

35.6398

Polarizability

14.680639

Polar Surface Area

35.53

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

diethyl methylphosphonate

IUPAC name

diethyl methylphosphonate

Synonyms

DiethylmethylphosphonateDEMPDiethoxymethylphosphine oxide双(二乙氧基氧膦基)甲烷甲基膦酸二乙酯Diethyl methylphosphonateBis(diethoxyphosphinyl)methane甲基磷酸二乙酯Diethyl methanephosphonateMethylphosphonic acid diethyl esterDiethyl methylphosphonate

Names and Identifiers

Registration numbers

MDL Number

MFCD00009813

PubChem CID

12685

PubChem SID

1620398542488320824856263

CAS Number

683-08-9

Beilstein Number

1753416

EC Number

211-667-4

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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.

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

• For synthetic applications of the lithio-derivatives of esters of methanephosphonic acid, see Dimethyl methylphosphonate, A14268.

• Reaction of the lithio-derivative with dialkyl cyanamides gives, instead of the expected 2-phosphorylacetamide, a rearranged N-phosphorylated amidine: Chem. Commun., 609 (1998):

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

diethyl methylphosphonate

IUPAC name

diethyl methylphosphonate

Synonyms

Registration numbers

MDL Number

MFCD00009813

PubChem CID

12685

PubChem SID

1620398542488320824856263

CAS Number

Beilstein Number

EC Number

Molecule Details

268119

64261

References

PubChem Literature

From Data Sources

• 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).

• For synthetic applications of the lithio-derivatives of esters of methanephosphonic acid, see Dimethyl methylphosphonate, A14268.

• Reaction of the lithio-derivative with dialkyl cyanamides gives, instead of the expected 2-phosphorylacetamide, a rearranged N-phosphorylated amidine: Chem. Commun., 609 (1998):

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:74936