diethyl benzylphosphonate

• ChemBase ID: 74905
• Molecular Formular: C11H17O3P
• Molecular Mass: 228.224641
• Monoisotopic Mass: 228.09153103
• SMILES: P(=O)(OCC)(OCC)Cc1ccccc1
• Canonical SMILES: CCOP(=O)(Cc1ccccc1)OCC
• InChI: InChI=1S/C11H17O3P/c1-3-13-15(12,14-4-2)10-11-8-6-5-7-9-11/h5-9H,3-4,10H2,1-2H3
• InChIKey: AIPRAPZUGUTQKX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl benzylphosphonate
• IUPAC Traditional name: diethyl benzylphosphonate
• Synonyms: Diethyl(benzyl)phosphonate; DIETHYLBENZYL PHOSPHONATE; Diethyl alpha-toluenephosphonate; (Diethoxyphosphonomethyl)benzene; Benzylphosphonic acid diethyl ester; NSC 62294; Diethyl benzylphosphonate; Diethyl benzylphosphonate; 苄基膦酸二乙酯

Database IDs

• CAS Number: 1080-32-6
• EC Number: 214-097-4
• MDL Number: MFCD00009078
• Beilstein Number: 2580931
• PubChem SID: 162039823; 24894251
• PubChem CID: 14122

CALCULATED PROPERTIES

• Polarizability: 24.202454 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.3396928
• LogD (pH = 7.4): 2.3396928
• Log P: 2.3396928
• Molar Refractivity: 60.3762 cm^3

PROPERTIES

Physical Property

• Boiling Point: 106-108 °C/1 mmHg(lit.); 106-108°C/1mm
• Flash Point: >110°C(230°F); >113 °C; >235.4 °F
• Density: 1.094; 1.095 g/mL at 25 °C(lit.)
• Refractive Index: 1.4975; n20/D 1.497(lit.)

Safety Information

• RTECS: SZ6600000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: 95+%; 99%
• Linear Formula: C6H5CH2P(O)(OC2H5)2

DETAILS

MP Biomedicals - 05210937

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D91071

Packaging
25, 100 g in glass bottle
Application
Reactant for synthesis of:
• 3,5-dihydroxy-4-isopropylstilbene for treatment of skin disorders1
• Natural cytotoxic marine products of polyketide origin via intramolecular Diels-Alder reactions2
• Stilbenes via on-column oxidation of vicinal diols and Horner-Emmons reactions3
• Inhibitors of teh Wnt pathway for colon cancer repression using Wadsworth-Emmons reactions4
• Antimalarial drug analogs against P. falciparum5Reactant for:
• Cyclization of aryl ethers, amines, and amides6
• Investigating the effects of functional groups on the performance of clue organic LEDs7

REFERENCES

• Horner-Wadsworth-Emmons reaction (see Appendix 1) with aromatic aldehydes gives stilbenes, almost exclusively trans: J. Org. Chem., 30, 680 (1965); J. Am. Chem. Soc., 83, 1733 (1961); 96, 1459 (1974). NaH + 15-crown-5 in THF promotes reaction with aldehydes and ketones at room temperature in excellent yields: Synthesis, 117 (1981). Phase-transfer reaction with cinnamaldehydes, using tetra-n-butylammonium iodide and NaOH gives diarylbutadienes: Synthesis, 187 (1976).
• See also 15-Crown-5, A12265.