diethyl {[methoxy(methyl)carbamoyl]methyl}phosphonate

• ChemBase ID: 74933
• Molecular Formular: C8H18NO5P
• Molecular Mass: 239.205981
• Monoisotopic Mass: 239.09225931
• SMILES: P(=O)(OCC)(OCC)CC(=O)N(OC)C
• Canonical SMILES: CCOP(=O)(CC(=O)N(OC)C)OCC
• InChI: InChI=1S/C8H18NO5P/c1-5-13-15(11,14-6-2)7-8(10)9(3)12-4/h5-7H2,1-4H3
• InChIKey: WYLRYBDGIILFIR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl {[methoxy(methyl)carbamoyl]methyl}phosphonate
• IUPAC Traditional name: diethyl [methoxy(methyl)carbamoyl]methylphosphonate
• Synonyms: Diethyl(N-methoxy-N-methylcarbamoylmethyl)phosphonate; N-Methoxy-N-methyl-2-(diethyl phosphono)acetamide; Diethyl N-methoxy-N-methylphosphonoacetamide; Diethylphosphonoacetic acid N-methyl-N-methoxyamide; Diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate; N-Methoxy-N-methyl-phosphonoacetamide diethyl ester; N-甲氧基-N-甲羰基甲基膦酸二乙酯

Database IDs

• CAS Number: 124931-12-0
• MDL Number: MFCD00134233
• Beilstein Number: 1875865
• PubChem SID: 24862312; 162039851
• PubChem CID: 2773719

CALCULATED PROPERTIES

• Acid pKa: 9.991959
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.05622206
• LogD (pH = 7.4): 0.055128127
• Log P: 0.056236025
• Molar Refractivity: 55.0616 cm^3
• Polarizability: 22.211113 Å^3
• Polar Surface Area: 65.07 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 90 °C/17 mmHg(lit.)
• Flash Point: 110 °C; 230 °F
• Density: 1.163 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.455(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: 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: 96%
• Linear Formula: CH3ON(CH3)COCH2P(O)(OC2H5)2

DETAILS

Sigma Aldrich - 362433

Application
Wittig carbonylating reagent.7
Reactant for:
• Preparation of ring-expanded bryostatin analogs as antitumor agents1
• Asymmertic synthesis of pinnatoxins A and G via diastereoselective Ireland-Claisen rearrangement, ring closing metathesis, and cyclization2
• Rh2(II)-catalyzed nitro-group migration reactions3
• Stereoselective synthesis of cyclohexanones via phase transfer catalyzed double addition reactions4
• Stereoselective synthesis of (+)-polyrhacitide A via aldol reaction, Horner-Wardsworth-Emmons reaction, Evans acetal intramolecular oxa-Michael reaction and diastereoselective syn reduction reaction as the key steps5
• Preparation of substituted furans via olefin cross-metathesis6
Packaging
1, 5 g in glass bottle