Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate

Base Information

• Chemical Name: Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate
• CAS No.: 40665-94-9
• Molecular Formula: C11H14ClO5P
• Molecular Weight: 292.656
• Hs Code.: 2931900090
• European Community (EC) Number: 620-947-9
• DSSTox Substance ID: DTXSID70393719
• Nikkaji Number: J24.888F
• Wikidata: Q72469623
• Mol file: 40665-94-9.mol

Synonyms:40665-94-9;Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate;Dimethyl (3-(3-chlorophenoxy)-2-oxopropyl)phosphonate;1-(3-chlorophenoxy)-3-dimethoxyphosphorylpropan-2-one;dimethyl [3-(3-chlorophenoxy)-2-oxopropyl]phosphonate;SCHEMBL6297069;Dimethyl [3-(3-chlorophenoxy)-2-oxoprop-1-yl]phosphonate;DTXSID70393719;ZNPUZMPUXAFKQZ-UHFFFAOYSA-N;AMY30094;MFCD00800277;Phosphonic acid, [3-(3-chlorophenoxy)-2-oxopropyl]-, dimethyl ester;AKOS015891032;AC-29280;BP-12995;CS-0204730;FT-0732158;E83594;A873255;Dimethyl[3-(3-chlorophenoxy)-2-oxoprop-1-yl]phosphonate;Dimethyl [3-(3-chlorophenoxy)-2-oxoprop-1 -yl]phosphonate;3-(m-Chlorophenoxy)-2-oxopropylphosphonic acid dimethyl ester;Phosphonic acid, P-[3-(3-chlorophenoxy) -2-oxopropyl]-,dimethyl ester

Chemical Property of Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate

Chemical Property:

• Vapor Pressure: 1.31E-06mmHg at 25°C
• Refractive Index: 1.504
• Boiling Point: 400.1 °C at 760 mmHg
• Flash Point: 303.5 °C
• PSA: 71.64000
• Density: 1.298 g/cm³
• LogP: 2.77380
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 292.0267382
• Heavy Atom Count: 18
• Complexity: 315

Purity/Quality:

98%, ^*data from raw suppliers

Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COP(=O)(CC(=O)COC1=CC(=CC=C1)Cl)OC
• Uses: Dimethyl 3-(3-Chlorophenoxy)-2-oxopropylphosphonate is an intermediate used in the synthesis of (+)-cloprostenol and α-pentanorbenzo analogs of prostaglandins.

Technology Process of Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate

There total 6 articles about Dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

methyl 2-(3-chlorophenoxy)acetate (74411-14-6) + dimethyl methane phosphonate (756-79-6) → dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate (40665-94-9)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

methyl 2-(3-chlorophenoxy)acetate; In tetrahydrofuran; at -78 - 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.2174/157017811795371485

Reference yield:

ethyl (3-chlorophenoxy)acetate (52094-98-1) + dimethyl methane phosphonate (756-79-6) → dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate (40665-94-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; ethyl acetate;

Reference yield:

dimethyl 3-(3-chlorophenoxy)-2-semicarbazonopropylphosphonate (63501-50-8) → dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate (40665-94-9)

Guidance literature:

With sodium hydrogencarbonate; In water; acetic acid; 2-oxo-propionic acid;

upstream raw materials:

methyl 2-(3-chlorophenoxy)acetate

dimethyl methane phosphonate

3-monochlorophenol

ethyl (3-chlorophenoxy)acetate

Downstream raw materials:

(3aR,4R,5R,6aS)-4-((E)-4-(3-chlorophenoxy)-3-oxobut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1′-biphenyl]-4-carboxylate

Isopropyl [2R(1E),3R(4Z),4R]-7-[Tetrahydro-2-[4-(3-chlorophenoxy)-3-oxo-1-butenyl]-4-(tetrahydropyran-2-yl)oxy-3-furanyl]-4-heptenoate

(+)-cloprostenol

Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-[(E)-(S)-4-(3-chloro-phenoxy)-3-hydroxy-but-1-enyl]-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Refernces

• 1、 Mudduluru, Harikrishna,Hindupur, Rama M.,Dubey, Pramod K.,Madhavaram, Shankar,Tatini, Lakshmikumar,Subbaraju, Gottumukkala V.. "Synthesis of (±) travoprost and its analogs". experimental part. p. 234 - 241. Retrieved 2012/04/18.
• 2、 -. "Use of 9-deoxy prostaglandin derivatives to treat glaucoma". . . Retrieved 2008/06/13.