Dimethyl methoxymethylenemalonate

Base Information

• Chemical Name: Dimethyl methoxymethylenemalonate
• CAS No.: 22398-14-7
• Molecular Formula: C7H10O5
• Molecular Weight: 174.153
• Hs Code.: 29171990
• European Community (EC) Number: 244-957-4
• NSC Number: 131266
• DSSTox Substance ID: DTXSID90176925
• Nikkaji Number: J41.171J
• Mol file: 22398-14-7.mol

Synonyms:22398-14-7;Dimethyl methoxymethylenemalonate;Dimethyl 2-(methoxymethylene)malonate;1,3-dimethyl 2-(methoxymethylidene)propanedioate;dimethyl 2-(methoxymethylidene)propanedioate;EINECS 244-957-4;MFCD00038225;Propanedioic acid, (methoxymethylene)-, dimethyl ester;dimethylmethoxymethylenemalonate;Methoxymethylenemalonic Acid Dimethyl Ester;SCHEMBL166090;dimethyl methoxymethylidenemalonate;DTXSID90176925;dimethyl (methoxymethylene)malonate;AMY14316;XAA39814;dimethyl methoxymethylenepropanedioate;AC9790;NSC131266;dimethyl methoxymethylene-propanedioate;AKOS016010185;FS-4252;NSC 131266;NSC-131266;dimethyl(methoxymethylidene)propanedioate;dimethyl (methoxymethylidene)propanedioate;methoxymethylenmalonic acid dimethyl ester;SY039657;CS-0119967;FT-0625087;M1207;EN300-67321;2-(Methoxymethylene)malonic acid dimethyl ester;W-107475

Chemical Property of Dimethyl methoxymethylenemalonate

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 0.292mmHg at 25°C
• Melting Point: 40-44 °C
• Refractive Index: 1.439
• Boiling Point: 202.5 °C at 760 mmHg
• Flash Point: 78.1 °C
• PSA: 61.83000
• Density: 1.154 g/cm³
• LogP: -0.13730
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 174.05282342
• Heavy Atom Count: 12
• Complexity: 188

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl2-(Methoxymethylene)malonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 43-36/38-22
• Safety Statements: 37/39-26-24

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC=C(C(=O)OC)C(=O)OC
• Uses: Dimethyl 2-(Methoxymethylene)malonate is a useful synthetic intermediate. It is used in preparation of (phenoxyethoxy)quinolones with antimalarial activities. It is also a reagent used in the synthesis of bicyclic pyridones prepn. as oral selective CB2 agonists with anti-pruritic activity.

Technology Process of Dimethyl methoxymethylenemalonate

There total 5 articles about Dimethyl methoxymethylenemalonate 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: 80.0%

(4R,5S)-5-Dimethoxymethyl-4-methoxy-4,5-dihydro-pyrazole-3,3-dicarboxylic acid dimethyl ester (99366-49-1) → dimethyl (methoxymethylene)malonate (22398-14-7) + 2-(2,3,3-Trimethoxy-propylidene)-malonic acid dimethyl ester (99366-53-7) + (2S,3R)-2-Dimethoxymethyl-3-methoxy-cyclopropane-1,1-dicarboxylic acid dimethyl ester (104286-66-0)

Guidance literature:

In toluene; at 20 - 25 ℃; for 10h; Yields of byproduct given; Irradiation;

DOI:10.1016/S0040-4020(01)97205-9

Reference yield: 80.0%

→ dimethyl (methoxymethylene)malonate (22398-14-7)

Guidance literature:

Reference yield:

hydroxymethylenemalonic acid dimethyl ester (27931-91-5) → dimethyl (methoxymethylene)malonate (22398-14-7)

Guidance literature:

With hydrogenchloride; In methanol; dichloromethane; acetonitrile;

upstream raw materials:

malonic acid dimethyl ester

trimethyl orthoformate

(R)-4-Methoxy-4,5-dihydro-pyrazole-3,3-dicarboxylic acid dimethyl ester

(4R,5S)-5-Dimethoxymethyl-4-methoxy-4,5-dihydro-pyrazole-3,3-dicarboxylic acid dimethyl ester

Downstream raw materials:

2-benzyl-1,1,3-trioxo-1,2,3,6-tetrahydro-1λ⁶-[1,2,6]thiadiazine-4-carboxylic acid methyl ester

Methyl 1-(t-Butyl)-1,2-dihydro-5-methyl-2-oxo-3-pyridinecarboxylate

Methyl 1,2-Dihydro-6-(p-methoxyphenyl)-2-oxo-3-pyridinecarboxylate

6-(4-Methoxy-benzoyl)-2-oxo-5,6,7,8-tetrahydro-2H-pyrano[3,2-c]pyridine-3-carboxylic acid methyl ester

Refernces

• 1、 -. "Process for the preparation of alkoxyalkylidenemalonic acid esters". . . Retrieved 2008/06/13.
• 2、 Katagiri, Nobuya,Haneda, Toru,Kaneko, Chikara. "FACILE SYNTHESIS OF THE CARBOCYCLIC ANALOGUE OF β-RIBOFURANOSYLMALONATE, NEW SYNTHON FOR CARBOCYCLIC C-NUCLEOSIDE FORMATION BY RETROGRADE ALDOL C-C BOND FISSION". . p. 4875 - 4878. Retrieved 2007/10/02.