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40665-68-7

Basic Information
CAS No.: 40665-68-7
Name: DIMETHYL(3-PHENOXY-2-OXOPROPYL)PHOSPHONATE
Article Data: 28
Molecular Structure:
Molecular Structure of 40665-68-7 (DIMETHYL(3-PHENOXY-2-OXOPROPYL)PHOSPHONATE)
Formula: C11H15O5P
Molecular Weight: 258.211
Synonyms: Phosphonicacid, (2-oxo-3-phenoxypropyl)-, dimethyl ester (9CI);(2-Oxo-3-phenoxypropyl)phosphonic acid dimethyl ester;Dimethyl(2-oxo-3-phenoxypropyl)phosphonate;Dimethyl (3-phenoxyacetonyl)phosphonate;Dimethyl 3-phenoxy-2-oxopropylphosphonate;
Density: 1.21 g/cm3
Boiling Point: 369.8 °C at 760 mmHg
Flash Point: 191.1 °C
Risk Codes: 36/37/38
Safety: 26-36/37/39
PSA: 71.64000
LogP: 2.12040
Synthetic route
2065-23-8

methyl 2-phenoxyacetate

756-79-6

dimethyl methane phosphonate

40665-68-7

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: methyl 2-phenoxyacetate In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere;
83%
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: methyl 2-phenoxyacetate In tetrahydrofuran at 25℃;
25%
With n-butyllithium 1.) THF, hexane, -78 deg C, 5 min, 2.) -78 deg C, 2 h; Yield given. Multistep reaction;
With n-butyllithium In tetrahydrofuran; hexane; water
2065-23-8

methyl 2-phenoxyacetate

34939-91-8, 58648-56-9

dimethyl lithiomethylphosphonate

40665-68-7

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions
ConditionsYield
In tetrahydrofuran at -78℃;
709-84-2

bis-tetrahydropyran-2-yl ether

109-72-8, 29786-93-4

n-butyllithium

701-99-5

Phenoxyacetyl chloride

756-79-6

dimethyl methane phosphonate

40665-68-7

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions
ConditionsYield
In tetrahydrofuran; hexane; water
2555-49-9

phenoxyacetic acid ethyl ester

756-79-6

dimethyl methane phosphonate

40665-68-7

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane
With n-butyllithium In tetrahydrofuran; hexane
701-99-5

Phenoxyacetyl chloride

756-79-6

dimethyl methane phosphonate

40665-68-7

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions
ConditionsYield
In tetrahydrofuran; hexane
In tetrahydrofuran; hexane
methyl 9α-acetoxy-11α-(2-tetrahydropyranyloxy)-15α-hdroxy-16-phenoxy-17,18,19,20-tetranorprosta-cis-5,trans-13-dienoate

methyl 9α-acetoxy-11α-(2-tetrahydropyranyloxy)-15α-hdroxy-16-phenoxy-17,18,19,20-tetranorprosta-cis-5,trans-13-dienoate

2555-49-9

phenoxyacetic acid ethyl ester

756-79-6

dimethyl methane phosphonate

40665-68-7

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane
108-95-2

phenol

40665-68-7

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate / acetone / 16 h / 25 - 56 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 2.5 h / -78 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water / 0.67 h / 25 °C
1.2: 16 h / 30 - 35 °C
2.1: zinc(II) chloride / toluene / 6 h / 65 - 70 °C / Inert atmosphere
3.1: Jones reagent / acetone / 7 h / Cooling with ice
View Scheme
122-60-1

Phenyl glycidyl ether

40665-68-7

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: zinc(II) chloride / toluene / 6 h / 65 - 70 °C / Inert atmosphere
2: Jones reagent / acetone / 7 h / Cooling with ice
View Scheme

2-hydroxy-3-phenoxypropyldimethylphosphonate

40665-68-7

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Conditions
ConditionsYield
With Jones reagent In acetone for 7h; Cooling with ice;92.8 g
40665-68-7

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

39746-01-5

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

51638-91-6

(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Conditions
ConditionsYield
With sodium hydride Horner-Emmons reaction;90%
Stage #1: dimethyl (3-phenoxy-2-oxopropyl)phosphonate With sodium hydride; zinc(II) chloride In tetrahydrofuran; mineral oil at 25 - 35℃; for 0.416667h; Inert atmosphere;
Stage #2: (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one In tetrahydrofuran; dichloromethane; mineral oil at 25 - 40℃; for 2.08333h; Inert atmosphere;
61%
Stage #1: dimethyl (3-phenoxy-2-oxopropyl)phosphonate With sodium hydroxide; zinc(II) chloride In tetrahydrofuran at 27℃; Inert atmosphere;
Stage #2: (1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one In tetrahydrofuran at 27℃; for 15h; Inert atmosphere;
50%
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    CAS No. 40665-68-7 Molecular formula C11H15O5P Molecular weight 258.20800 Accurate mass 258.06600 Density: 1.209g/cm 3 Boiling point: 369.8ºC at 760 mmHg Flash point: 191.1 ºC Refra

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Specification

The Dimethyl (3-phenoxy-2-oxopropyl)phosphonate with the CAS number 40665-68-7 is also called Phosphonic acid,P-(2-oxo-3-phenoxypropyl)-, dimethyl ester. Its systematic name is 1-dimethoxyphosphoryl-3-phenoxypropan-2-one. Its molecular formula is C11H15O5P.

The properties of the Dimethyl (3-phenoxy-2-oxopropyl)phosphonate are: (1)ACD/LogP: 1.07; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.07; (4)ACD/LogD (pH 7.4): 1.07; (5)ACD/BCF (pH 5.5): 3.86; (6)ACD/BCF (pH 7.4): 3.86; (7)ACD/KOC (pH 5.5): 91.52; (8)ACD/KOC (pH 7.4): 91.52; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 71.64 Å2; (13)Index of Refraction: 1.491; (14)Molar Refractivity: 61.85 cm3; (15)Molar Volume: 213.4 cm3; (16)Polarizability: 24.52×10-24cm3; (17)Surface Tension: 40.8 dyne/cm; (18)Enthalpy of Vaporization: 61.66 kJ/mol; (19)Vapour Pressure: 1.16×10-5 mmHg at 25°C.

Uses: Dimethyl (3-phenoxy-2-oxopropyl)phosphonate can react with 11-(2-formyl-5-oxo-cyclopentyl)-undecanoic acid methyl ester to prepare 11-[2-oxo-5-(3-oxo-4-phenoxy-but-1-enyl)-cyclopentyl]-undecanoic acid methyl ester. This reaction needs reagent KOH and solvent CH2Cl2 at Ambient temperature. The reaction time is 1.0 hour. The yield is 50%.

While using Dimethyl (3-phenoxy-2-oxopropyl)phosphonate, you should be very cautious. This chemical is not only irritating to skin, but also irritating to eyes and respiratory system. Therefore, you should take the following instructions. Firstly, you should wear suitable protective clothing, gloves and eye/face protection. Then in case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=P(OC)(OC)CC(=O)COc1ccccc1;
(2)InChI: InChI=1/C11H15O5P/c1-14-17(13,15-2)9-10(12)8-16-11-6-4-3-5-7-11/h3-7H,8-9H2,1-2H3;
(3)InChIKey: NQTSTBMCCAVWOS-UHFFFAOYAM;