2-Chloromethylene-malonic acid diethyl ester

Base Information

• Chemical Name: 2-Chloromethylene-malonic acid diethyl ester
• CAS No.: 28783-51-9
• Molecular Formula: C8H11ClO4
• Molecular Weight: 206.626
• Hs Code.: 2917190090
• DSSTox Substance ID: DTXSID60447674
• Nikkaji Number: J2.989.575I
• Mol file: 28783-51-9.mol

Synonyms:28783-51-9;2-Chloromethylene-malonic acid diethyl ester;diethyl 2-(chloromethylene)malonate;Diethyl 2-(chloromethylidene)propanedioate;Diethyl2-(chloromethylene)malonate;2-(Chloromethylene)malonic acid diethyl ester;SCHEMBL5785348;DTXSID60447674;PRHVDTPQGCSBCY-UHFFFAOYSA-N;MFCD03839834;AKOS025402232;AC-6746;DS-11859;A5429;CS-0172264;FT-0687227;1,3-DIETHYL 2-(CHLOROMETHYLIDENE)PROPANEDIOATE;2-CHLOROMETHYLENE-MALONIC ACID DIETHYL ESTER;5-(2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate, hydrochloride

Chemical Property of 2-Chloromethylene-malonic acid diethyl ester

Chemical Property:

• Vapor Pressure: 0.192mmHg at 25°C
• Refractive Index: 1.462
• Boiling Point: 210.5 °C at 760 mmHg
• Flash Point: 74 °C
• PSA: 52.60000
• Density: 1.198 g/cm³
• LogP: 1.23530
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 206.0345865
• Heavy Atom Count: 13
• Complexity: 202

Purity/Quality:

99%, ^*data from raw suppliers

2-Chloromethylene-malonicAcidDiethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=CCl)C(=O)OCC

Technology Process of 2-Chloromethylene-malonic acid diethyl ester

There total 4 articles about 2-Chloromethylene-malonic acid diethyl ester 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: 77.0%

diethyl 2-(hydroxymethylene)malonate (20734-18-3) → diethyl 2-(chloromethylene)malonate (28783-51-9)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In toluene; Heating;

DOI:10.1016/S0957-4166(97)00018-9

Reference yield:

diethyl 2-ethoxymethylenemalonate (87-13-8) → diethyl 2-(chloromethylene)malonate (28783-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium hydroxide / tetrahydrofuran; water / 0 °C / Inert atmosphere

2: N,N-dimethyl-formamide; thionyl chloride / toluene / 100 °C / Inert atmosphere

With thionyl chloride; N,N-dimethyl-formamide; lithium hydroxide; In tetrahydrofuran; water; toluene;

DOI:10.1002/chem.201405094

Reference yield:

chloro-maleic acid diethyl ester (626-10-8) → diethyl 2-(chloromethylene)malonate (28783-51-9)

Guidance literature:

With toluene-4-sulfonic acid;

upstream raw materials:

chloro-maleic acid diethyl ester

diethyl α-formylmalonate

diethyl 2-(hydroxymethylene)malonate

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

diethyl-2-(4-methoxybenzylidene)malonate

diethyl 2-(4-methylbenzylidene)malonate

diethyl methoxymethylenemalonate

diethyl 2-ethoxymethylenemalonate

Refernces

• 1、 Le Goff, Ronan,Martel, Arnaud,Sanselme, Morgane,Lawson, Ata Martin,Dach, Adam,Comesse, Sbastien. "Simple access to highly functional bicyclic γ- and δ-lactams: Origins of chirality transfer to contiguous tertiary/quaternary stereocenters assessed by DFT". supporting information. p. 2966 - 2979. Retrieved 2015/02/19.