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Phosphonic acid,P-(2-oxo-2-phenylethyl)-, diethyl ester

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Name

Phosphonic acid,P-(2-oxo-2-phenylethyl)-, diethyl ester

EINECS N/A
CAS No. 3453-00-7 Density 1.144 g/cm3
PSA 62.41000 LogP 3.13540
Solubility N/A Melting Point N/A
Formula C12H17O4P Boiling Point 373.4 °C at 760 mmHg
Molecular Weight 256.238 Flash Point 193.2 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 3453-00-7 (DIETHYL (2-OXO-2-PHENYLETHYL)PHOSPHONATE) Hazard Symbols N/A
Synonyms

Phosphonicacid, (2-oxo-2-phenylethyl)-, diethyl ester (9CI);Phosphonic acid, phenacyl-,diethyl ester (6CI,7CI,8CI);(2-Oxo-2-phenylethyl)phosphonic acid diethylester;Diethyl (2-oxo-2-phenylethyl)phosphonate;Diethyl(2-oxophenethyl)phosphonate;Diethyl 2-oxo-2-phenylethanephosphonate;Diethylbenzoylmethanephosphonate;Diethyl benzoylmethylphosphonate;Diethylphenacylphosphonate;NSC 648426;

Article Data 104

Phosphonic acid,P-(2-oxo-2-phenylethyl)-, diethyl ester Synthetic route

3450-67-7

diethyl phenylethynylphosphonate

3453-00-7

diethyl benzoylmethylphosphonate

Conditions
ConditionsYield
With 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl gold(I) bis(trifluoromethanesulfonyl)imide; water In 1,2-dichloro-ethane at 20℃; for 12h; Reagent/catalyst; Solvent; regioselective reaction;96%
With water; palladium dichloride In 1,4-dioxane at 80℃; for 2h;95%
Stage #1: diethyl phenylethynylphosphonate With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); 2-iodophenylamine In 1,2-dichloro-ethane; toluene at 60℃; for 24h;
Stage #2: With hydrogenchloride; water In 1,2-dichloro-ethane; toluene at 20℃; for 0.25h;
94%
93-58-3

benzoic acid methyl ester

683-08-9

Diethyl methylphosphonate

3453-00-7

diethyl benzoylmethylphosphonate

Conditions
ConditionsYield
Stage #1: benzoic acid methyl ester; Diethyl methylphosphonate In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
96%
With lithium hexamethyldisilazane In tetrahydrofuran Barbier reaction; Cooling with ice; Inert atmosphere;91%
With n-butyllithium In tetrahydrofuran at -78 - 20℃;80%
Stage #1: Diethyl methylphosphonate With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: benzoic acid methyl ester In tetrahydrofuran at -78℃; for 5h;
50%
With lithium diisopropyl amide In tetrahydrofuran at -5℃; for 0.5h; Inert atmosphere;
683-08-9

Diethyl methylphosphonate

939-48-0

isopropyl benzoate

3453-00-7

diethyl benzoylmethylphosphonate

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran Barbier reaction; Cooling with ice; Inert atmosphere;93%
536-74-3

phenylacetylene

762-04-9

phosphonic acid diethyl ester

A

3450-67-7

diethyl phenylethynylphosphonate

B

3453-00-7

diethyl benzoylmethylphosphonate

Conditions
ConditionsYield
With tributyl-amine In dimethyl sulfoxide at 60℃; for 12h;A n/a
B 93%
140-10-3

(E)-3-phenylacrylic acid

762-04-9

phosphonic acid diethyl ester

3453-00-7

diethyl benzoylmethylphosphonate

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; oxygen In acetonitrile at 60℃; for 6h; Reagent/catalyst; Solvent; Temperature;92%
With iron(III) chloride; copper(II) bis(trifluoromethanesulfonate); triethylamine In dimethyl sulfoxide at 70℃; for 8h; Schlenk technique;78%
16717-64-9

1-azidostyrene

762-04-9

phosphonic acid diethyl ester

3453-00-7

diethyl benzoylmethylphosphonate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 6h; Sealed tube;92%
762-04-9

phosphonic acid diethyl ester

3453-00-7

diethyl benzoylmethylphosphonate

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; oxygen In acetonitrile at 60℃; for 3h; Reagent/catalyst; Temperature; Solvent;91%
With copper(ll) sulfate pentahydrate In acetonitrile at 60℃; for 2h;91%
With di-tert-butyl peroxide; copper(II) ferrite; triethylamine In acetonitrile at 85℃; for 6h; Reagent/catalyst; Temperature; Solvent;80%
103517-92-6

[2-(Methoxycarbonyl-hydrazono)-2-phenyl-ethyl]-phosphonic acid diethyl ester

3453-00-7

diethyl benzoylmethylphosphonate

Conditions
ConditionsYield
With hydrogenchloride; acetone for 3h; Ambient temperature;90%
536-74-3

phenylacetylene

762-04-9

phosphonic acid diethyl ester

3453-00-7

diethyl benzoylmethylphosphonate

Conditions
ConditionsYield
With dipotassium peroxodisulfate; copper(ll) sulfate pentahydrate; silver nitrate In dichloromethane; water at 20℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent;89%
With iron(III) chloride; oxygen; copper(I) triflate; triethylamine In dimethyl sulfoxide at 70℃; for 24h; Reagent/catalyst; Solvent; Temperature; Concentration; Sealed tube;70%
With iron(III) chloride; copper acetylacetonate; oxygen; triethylamine In dimethyl sulfoxide at 80℃; for 24h; Reagent/catalyst; Solvent; Temperature; Concentration;63%
683-08-9

Diethyl methylphosphonate

98-88-4

benzoyl chloride

3453-00-7

diethyl benzoylmethylphosphonate

Conditions
ConditionsYield
Stage #1: Diethyl methylphosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h;
Stage #2: With copper(I) bromide In tetrahydrofuran; hexane at -60 - -30℃; for 1.5h;
Stage #3: benzoyl chloride In tetrahydrofuran; hexane at -40 - -30℃; Further stages.;
86%
(i) nBuLi, hexane, THF, (ii) Cu2I2, (iii) /BRN= 471389/, Et2O; Multistep reaction;

Phosphonic acid,P-(2-oxo-2-phenylethyl)-, diethyl ester Specification

The Phosphonic acid, P-(2-oxo-2-phenylethyl)-, diethyl ester, with the CAS registry number of 3453-00-7, is also known as Diethyl (2-oxo-2-phenylethyl)phosphonate and (2-Oxo-2-phenylethyl)phosphonic acid diethyl ester. It belongs to the product categories of C-C Bond Formation; Horner-Wadsworth-Emmons Reagents; Olefination. This chemical's molecular formula is C12H17O4P and molecular weight is 256.23. What's more, its IUPAC name is 2-Diethoxyphosphoryl-1-phenylethanone. In addition, it must be stored in airtight containers and placed in a dry, ventilated place at room temperature. Meanwhile, it should avoid contact with light.

Physical properties about Phosphonic acid, P-(2-oxo-2-phenylethyl)-, diethyl ester are: (1)ACD/LogP: 1.76; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 4; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 7; (6)Polar Surface Area: 62.41 Å2; (7)Index of Refraction: 1.494; (8)Molar Refractivity: 65.17 cm3; (9)Molar Volume: 223.8 cm3; (10)Polarizability: 25.83×10-24 cm3; (11)Surface Tension: 40 dyne/cm; (12)Density: 1.144 g/cm3; (13)Flash Point: 193.2 °C; (14)Enthalpy of Vaporization: 62.06 kJ/mol; (15)Boiling Point: 373.4 °C at 760 mmHg; (16)Vapour Pressure: 9.01E-06 mmHg at 25 °C.

Preparation: this chemical is prepared by reaction of 2-Bromo-1-phenyl-ethanone with Phosphorous acid triethyl ester. The reaction needs solvent Diethyl ether. The reaction temperature is 10 °C. The yield is about 63 %.

 

Uses: it is used to produce other chemicals. For example, it is used to produce (2-Amino-2-phenyl-ethyl)-phosphonic acid diethyl ester at ambient temperature. This reaction needs reagents Acetate ammonium, Cyanoborohydrure sodium, HCl. Meanwhile, it needs solvent Methanol. The reaction time is 4 hours. The yield is about 62 %.

 

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(c1ccccc1)CP(=O)(OCC)OCC
(2) InChI: InChI=1/C12H17O4P/c1-3-15-17(14,16-4-2)10-12(13)11-8-6-5-7-9-11/h5-9H,3-4,10H2,1-2H3
(3) InChIKey: HPEVTTNSIPGLEL-UHFFFAOYAE

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