Citraconic acid, dimethyl ester

Base Information

• Chemical Name: Citraconic acid, dimethyl ester
• CAS No.: 617-54-9
• Molecular Formula: C7H10 O4
• Molecular Weight: 158.154
• Hs Code.: 2917190090
• NSC Number: 43975
• DSSTox Substance ID: DTXSID00883471
• Nikkaji Number: J16.836J
• Mol file: 617-54-9.mol

Synonyms:dimethylcitraconate

Chemical Property of Citraconic acid, dimethyl ester

Chemical Property:

• Refractive Index: 1.4460-1.4490
• Boiling Point: 211 °C
• Flash Point: 91.5oC
• PSA: 52.60000
• Density: 1,11 g/cm3
• LogP: 0.27870
• Storage Temp.: Sealed in dry,Room Temperature
• 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%,99%, ^*data from raw suppliers

Dimethyl Citraconate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

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 Citraconate is a useful synthetic intermediate. It has been used in the synthesis of natural products chaetomellic acid A anhydride and 1,7(Z)- nonadecadiene-2,3-dicarboxylic acid. It is also used to prepare acyclic alkanes by reduction using homogeneous catalysts or biocatalysts.

Technology Process of Citraconic acid, dimethyl ester

There total 13 articles about Citraconic acid, dimethyl 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: 100.0%

methanol (67-56-1) + citraconic acid (498-23-7,7407-59-2) → citraconic acid dimethyl ester (617-54-9)

Guidance literature:

With boron trifluoride; at 65 ℃; for 0.333333h;

DOI:10.1021/ac049919h

Reference yield: 100.0%

methanol (67-56-1) + citraconic acid anhydride (616-02-4) → citraconic acid dimethyl ester (617-54-9)

Guidance literature:

With sulfuric acid; for 12h; Heating;

DOI:10.1016/j.tet.2004.07.081

Reference yield: 93.0%

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

Guidance literature:

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

dimethyl acetylenedicarboxylate; In tetrahydrofuran; at -78 ℃; for 0.666667h;

DOI:10.1055/s-2002-25344

upstream raw materials:

methanol

citraconic acid

citraconic acid anhydride

methyllithium

Downstream raw materials:

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

dimethyl 2-(methoxymethyl)succinate

tricarallylic acid

Citraconsaeurediamid

Refernces

• 1、 Nonaka,Abe,Fuchigami. "ELECTRO-ORGANIC REACTIONS ON ORGANIC ELECTRODES. PART 2. ELECTROCHEMICAL ASYMMETRIC REDUCTION OF CITRACONIC AND MESACONIC ACIDS ON OPTICALLY-ACTIVE POLY(AMINO ACID)-COATED ELECTRODES.". . p. 2778 - 2783. Retrieved 1983.
• 2、 Letcher, R. M.,Acheson, R. M.. "Vicinal C,H Spin Coupling Constants in Determining Alkene Stereochemistry". . p. 316 - 318. Retrieved 1981.
• 3、 álvarez, José María,Jorge, Zacarías D.,Massanet, Guillermo M.. "Study of the Oxidative Cleavage Proposed in the Biogenesis of Transtaganolides/Basiliolides: Pyran-2-one Aromaticity-Mediated Regioselective Control and Biogenetic Implications". . . Retrieved 2020/03/05.
• 4、 Hintermair, Ulrich,Francio, Giancarlo,Leitner, Walter. "A fully integrated continuous-flow system for asymmetric catalysis: Enantioselective hydrogenation with supported ionic liquid phase catalysts using supercritical CO2 as the mobile phase". . p. 4538 - 4547. Retrieved 2013/05/08.