Dimethyl (2-oxoheptyl)phosphonate

Base Information

• Chemical Name: Dimethyl (2-oxoheptyl)phosphonate
• CAS No.: 36969-89-8
• Molecular Formula: C9H19O4P
• Molecular Weight: 222.221
• Hs Code.: 2931900090
• European Community (EC) Number: 253-293-4
• DSSTox Substance ID: DTXSID30190463
• Nikkaji Number: J21.055B
• Wikidata: Q72471120
• Mol file: 36969-89-8.mol

Synonyms:Dimethyl (2-oxoheptyl)phosphonate;36969-89-8;1-dimethoxyphosphorylheptan-2-one;dimethyl(2-oxoheptyl)phosphonate;Dimethyl 2-oxoheptylphosphonate;Phosphonic acid, (2-oxoheptyl)-, dimethyl ester;EINECS 253-293-4;Dimethyl (2-oxoheptyl)-phosphonate;C9H19O4P;SCHEMBL2304429;dimethyl 2-oxoheptyl phosphonate;LQZCYXCHWNQBKX-UHFFFAOYSA-;DTXSID30190463;2-Oxoheptylphosphonic acid dimethyl;dimethyl-(2-oxo-heptyl)phosphonate;AMY30099;BCP16204;MFCD00009514;AKOS015899104;2-oxoheptylphosphonic acid dimethyl ester;AC-30869;AS-61398;(2-Oxoheptyl)phosphonic Acid Dimethyl Ester;CS-0152335;D4244;FT-0639352;F52652;Phosphonic acid, P-(2-oxoheptyl)-, dimethyl ester;Dimethyl 2-oxoheptylphosphonate, technical grade, 85%;(R)-methyl 2-(N-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoate

Chemical Property of Dimethyl (2-oxoheptyl)phosphonate

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.000423mmHg at 25°C
• Refractive Index: n20/D 1.444(lit.)
• Boiling Point: 316 °C at 760 mmHg
• Flash Point: 147.6 °C
• PSA: 62.41000
• Density: 1.052 g/cm³
• LogP: 2.62170
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 222.10209608
• Heavy Atom Count: 14
• Complexity: 207

Purity/Quality:

99.5% ^*data from raw suppliers

Dimethyl 2-oxoheptylphosphonate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)CP(=O)(OC)OC
• Uses: Dimethyl (2-Oxoheptyl)phosphonate is a useful synthetic intermediate, and is used as a reagent to synthesize Caffeic acid (C080000) derivatives, which function as 5-lipoxygenase, 12-lipoxygenase, and prostaglandin synthase inhibitors.

Technology Process of Dimethyl (2-oxoheptyl)phosphonate

There total 8 articles about Dimethyl (2-oxoheptyl)phosphonate 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: 90.0%

methyl hexanoate (106-70-7) + dimethyl methane phosphonate (756-79-6) → dimethyl 2-oxoheptylphosphonate (36969-89-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -5 - 0 ℃; for 1.5h; Inert atmosphere;

Reference yield:

hexanoic acid (142-62-1) → dimethyl 2-oxoheptylphosphonate (36969-89-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 10 - 20 °C / Inert atmosphere

2.1: dichloromethane / 1 h / 5 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -75 °C / Inert atmosphere

3.2: 1 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; thionyl chloride; N,N-dimethyl-formamide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.14233/ajchem.2013.13139

Reference yield:

Hexanoyl chloride (142-61-0) → dimethyl 2-oxoheptylphosphonate (36969-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / 1 h / 5 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - -75 °C / Inert atmosphere

2.2: 1 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.14233/ajchem.2013.13139

upstream raw materials:

1-bromo-butane

dimethyl (2-oxopropyl)phosphonate

Hexanoyl chloride

dimethyl methane phosphonate

Downstream raw materials:

[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester

3-(3-methoxy-2-nitrophenyl)-1-pentylpropen-1-one

Toluene-4-sulfonic acid 2-methoxy-6-((E)-3-oxo-oct-1-enyl)-phenyl ester

3-(2-benzenesulfonyloxy-3-methoxy-6-nitrophenyl)-1-pentylpropen-1-one

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF TREPROSTINIL". Page/Page column 48; 49. . Retrieved 2016/05/02.
• 2、 Hayashi, Kyohei,Tanimoto, Hiroki,Zhang, Huan,Morimoto, Tsumoru,Nishiyama, Yasuhiro,Kakiuchi, Kiyomi. "Efficient synthesis of α,β-unsaturated alkylimines performed with allyl cations and azides: Application to the synthesis of an ant venom alkaloid". supporting information. p. 5728 - 5731. Retrieved 2013/01/15.