Dimethyl citraconate

Base Information

• Chemical Name: Dimethyl citraconate
• CAS No.: 617-53-8
• Molecular Formula: C7H10O4
• Molecular Weight: 158.154
• DSSTox Substance ID: DTXSID201031523
• Metabolomics Workbench ID: 70109
• Nikkaji Number: J1.287.214C,J45.118E
• NSC Number: 226153
• Wikidata: Q27106419
• Mol file: 617-53-8.mol

Synonyms:dimethylcitraconate

Chemical Property of Dimethyl citraconate

Chemical Property:

• Refractive Index: 1.4512 (estimate)
• Boiling Point: 210.5°Cat760mmHg
• Flash Point: 91.5°C
• PSA: 52.60000
• Density: 1.094g/cm³
• LogP: 0.27870
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 193

Purity/Quality:

98%min ^*data from raw suppliers

DimethylMesaconate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)OC)C(=O)OC
• Isomeric SMILES: C/C(=C\C(=O)OC)/C(=O)OC
• Uses: Dimethyl Mesaconate is a substrate of old yellow enzyme.

Technology Process of Dimethyl citraconate

There total 3 articles about Dimethyl citraconate 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: 76.0%

methylmagnesium bromide (75-16-1) + dimethyl acetylenedicarboxylate (762-42-5) → citraconic acid dimethyl ester (617-54-9) + mesaconic acid dimethyl ester (617-53-8)

Guidance literature:

methylmagnesium bromide; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -40 ℃; for 2h;

dimethyl acetylenedicarboxylate; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1002/anie.201402034

Reference yield:

Dimethyl itakonate (617-52-7) → mesaconic acid dimethyl ester (617-53-8) + methyl 2-methylsuccinate (21307-96-0,22644-27-5,63163-08-6,1604-11-1) + C7H11(2)HO4 + dimethyl 2H1-methylfumarate (942305-19-3)

Guidance literature:

With trisodium tris(3-sulfophenyl)phosphine; water; sodium formate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In cyclohexane; at 30 - 60 ℃; Title compound not separated from byproducts;

DOI:10.1002/1099-0682(200007)2000:7<1495::AID-EJIC1495>3.0.CO;2-J

Reference yield:

Dimethyl itakonate (617-52-7) → mesaconic acid dimethyl ester (617-53-8) + methyl 2-methylsuccinate (21307-96-0,22644-27-5,63163-08-6,1604-11-1)

Guidance literature:

With trisodium tris(3-sulfophenyl)phosphine; water; sodium formate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In cyclohexane; at 39.85 ℃; Further Variations:; catalyst, initial substrate, reagent concentration; Kinetics;

DOI:10.1002/1099-0682(200007)2000:7<1495::AID-EJIC1495>3.0.CO;2-J

upstream raw materials:

Dimethyl itakonate

methylmagnesium bromide

dimethyl acetylenedicarboxylate

Downstream raw materials:

3-methyl-1H-pyrazole-4-carboxylic acid

(+/-)-4-methoxy-1-methyl-cyclohex-4-ene-1r,2t-dicarboxylic acid dimethyl ester

2-methyl-fumaramide

(+/-)-1-methyl-cyclohex-4-ene-1r,2t-dicarboxylic acid dimethyl ester

Refernces

• 1、 Tanchoux, Nathalie,De Bellefon, Claude. "Kinetic and mechanistic study of the H-transfer reduction of dimethyl itaconate by a Rh/TPPTS catalyst under biphasic conditions: Evidence for a rhodametallacycle intermediate". . p. 1495 - 1502. Retrieved 2007/10/03.