Diethyl 2-(iodomethyl)cyclopropane-1,1-dicarboxylate

Base Information

• Chemical Name: Diethyl 2-(iodomethyl)cyclopropane-1,1-dicarboxylate
• CAS No.: 144296-42-4
• Molecular Formula: C10H15 I O4
• Molecular Weight: 326.131
• DSSTox Substance ID: DTXSID90451062
• Nikkaji Number: J2.129.093I
• Mol file: 144296-42-4.mol

Synonyms:144296-42-4;Diethyl 2-(iodomethyl)cyclopropane-1,1-dicarboxylate;2-IODOMETHYL-CYCLOPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER;DTXSID90451062;WBUCLLNNEFPGAF-UHFFFAOYSA-N;AKOS015962665;2-(Iodomethyl)cyclopropane-1,1-dicarboxylic acid diethyl ester

Chemical Property of Diethyl 2-(iodomethyl)cyclopropane-1,1-dicarboxylate

Chemical Property:

• Boiling Point: 300.9±12.0 °C(Predicted)
• PSA: 52.60000
• Density: 1.632±0.06 g/cm3(Predicted)
• LogP: 1.55390
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 326.00151
• Heavy Atom Count: 15
• Complexity: 246

Purity/Quality:

99%min ^*data from raw suppliers

2-IODOMETHYL-CYCLOPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1(CC1CI)C(=O)OCC

Technology Process of Diethyl 2-(iodomethyl)cyclopropane-1,1-dicarboxylate

There total 2 articles about Diethyl 2-(iodomethyl)cyclopropane-1,1-dicarboxylate 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: 72.0%

(2-propenyl)propanedioic acid diethyl ester (2049-80-1) → 2-iodomethyl-cyclopropane-1,1-dicarboxylic acid diethyl ester (144296-42-4)

Guidance literature:

(2-propenyl)propanedioic acid diethyl ester; With pyridine; titanium(IV) isopropylate; iodine; In dichloromethane; at 20 ℃; for 45h;

With potassium permanganate; at 0 ℃; for 0.833333h;

DOI:10.1021/jm040149b

Reference yield:

diethyl 2-allyl-2-iodomalonate (144296-43-5) → 2-iodomethyl-cyclopropane-1,1-dicarboxylic acid diethyl ester (144296-42-4)

Guidance literature:

With sodium iodide; In tetrahydrofuran; Heating;

DOI:10.1016/S0040-4039(00)61249-2

Reference yield: 46.0%

2-iodomethyl-cyclopropane-1,1-dicarboxylic acid diethyl ester (144296-42-4) → 2-thiiranylmethyl-malonic acid diethyl ester + (2-propenyl)propanedioic acid diethyl ester (2049-80-1)

Guidance literature:

With sodium hydrogensulfide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2004.11.087

upstream raw materials:

(2-propenyl)propanedioic acid diethyl ester

diethyl 2-allyl-2-iodomalonate

Downstream raw materials:

diethyl 1-(phenylselenyl)methylcyclopropane-2,2-dicarboxylate

(2-propenyl)propanedioic acid diethyl ester

diethyl methylenecyclopropane-1,1-dicarboxylate ester

diethyl 1-(phenylselenyl)methylcyclopropane-2,2-dicarboxylate selenium oxide

Refernces

• 1、 Beckwith, Athelstan L. J.,Tozer, Matthew J.. "The iodination and iodocyclisation of some alkenylmalonates". . p. 4975 - 4978. Retrieved 2007/10/02.