Methylsuccinic acid

Base Information

• Chemical Name: Methylsuccinic acid
• CAS No.: 498-21-5
• Deprecated CAS: 636-60-2
• Molecular Formula: C₅H₈O₄
• Molecular Weight: 132.116
• Hs Code.: 29171900
• European Community (EC) Number: 207-857-1
• NSC Number: 5276
• UNII: H1547KG7UZ
• DSSTox Substance ID: DTXSID9025663
• Nikkaji Number: J6.105K
• Wikipedia: 2-Methylsuccinic_acid
• Wikidata: Q27163205
• Metabolomics Workbench ID: 2031
• Mol file: 498-21-5.mol

Synonyms:2-methylbutanedioic acid;methylsuccinic acid;methylsuccinic acid, (+-)-isomer

Chemical Property of Methylsuccinic acid

Chemical Property:

• Appearance/Colour: white to beige crystalline powder
• Vapor Pressure: 0.0162mmHg at 25°C
• Melting Point: 110-115 °C
• Refractive Index: 1.474
• Boiling Point: 236.5 °C at 760 mmHg
• PKA: 4.13(at 25℃)
• Flash Point: 111.1 °C
• PSA: 74.60000
• Density: 1.311 g/cm³
• LogP: 0.18180
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)
• Water Solubility.: Soluble in water.
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 132.04225873
• Heavy Atom Count: 9
• Complexity: 129

Purity/Quality:

99% ^*data from raw suppliers

Methylsuccinic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC(CC(=O)O)C(=O)O
• Description: Methylsuccinic acid is a normal metabolite found in human fluids and is an intermediate metabolite in the breakdown of fatty acids. Increased urinary levels of methylsuccinic acid (together with ethylmalonic acid) are the main biochemical measurable features in ethylmalonic encephalopathy.
• Uses: Methylsuccinic acid is used as a flux material and an important dyestuff intermediate. It is also used as an intermediate in medicine and pharmaceuticals.

Technology Process of Methylsuccinic acid

There total 190 articles about Methylsuccinic acid 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%

2-methylenesuccinic acid (97-65-4,25119-64-6) → 2-methylbutanedioic acid (498-21-5,636-60-2)

Guidance literature:

With hydrogen; (-)-(η⁵-2-menthyl-4,7-dimethylindenyl)Rh(dppe); In methanol; at 60 - 70 ℃; for 4h; under 10500.8 Torr; Further Variations:; Catalysts; Product distribution;

DOI:10.1002/1099-0682(20021)2002:1<211::AID-EJIC211>3.0.CO;2-3

Reference yield: 99.0%

citraconic acid (498-23-7,7407-59-2) → 2-methylbutanedioic acid (498-21-5,636-60-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; at 20 ℃; for 24h; atmospheric pressure;

DOI:10.1002/anie.200605168

Reference yield: 99.0%

methylbutenedioic acid (7407-59-2) → 2-methylbutanedioic acid (498-21-5,636-60-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; ethanol; at 20 ℃; for 24h; under 760.051 Torr;

DOI:10.1016/j.tet.2009.11.065

upstream raw materials:

3-methyltetrahydrofuran

2-butenoic acid

3-bromo-4-methyl-2,5-furandione

allyl iodid

Downstream raw materials:

2-carboxyisobutyrophenone

Diethyl 2-methylsuccinate

Mesaconic acid

2-methylsuccinic acid 1-methyl ester

Refernces

• 1、 Holzh?user, F. Joschka,Artz, Jens,Palkovits, Stefan,Kreyenschulte, Dirk,Büchs, Jochen,Palkovits, Regina. "Electrocatalytic upgrading of itaconic acid to methylsuccinic acid using fermentation broth as a substrate solution". . p. 2390 - 2397. Retrieved 2017.
• 2、 Wood, Joseph,Turner, Paul H.. "Monitoring of itaconic acid hydrogenation in a trickle bed reactor using fiber-optic coupled near-infrared spectroscopy". . p. 293 - 298. Retrieved 2003.
• 3、 Hoberg, Heinz,Ballesteros, Alfredo,Sigan, Andrei,Jegat, Corine,Baerhausen, Dieter,Milchereit, Armin. "Ligandgesteuerte Ringkontraktion von Nickela-Fuenf- in Vierringkomplexe-neuartige Startsysteme fuer die praeparative Chemie". . p. C23 - C29. Retrieved 1991.
• 4、 Botteghi et al.. "". . p. 221,223,224,225,227. Retrieved 1977.
• 5、 Lange, Susanne,Leitner, Walter. "Mechanistic aspects of hydrogen addition during enantioselective rhodium-catalysed reduction of C=C double bonds with formic acid/triethylamine or molecular hydrogen". . p. 752 - 758. Retrieved 2002.
• 6、 -. "CATALYST AND METHOD OF HYDROGENATING UNSATURATED COMPOUND WITH MULTI-CARBOXYLIC ACID GROUPS". Paragraph 0024-0040; 0042. . Retrieved 2021/06/26.
• 7、 Reed, John H.,Cramer, Nicolai. "1,3,2-Diazaphospholenes Catalyze the Conjugate Reduction of Substituted Acrylic Acids". . p. 4262 - 4266. Retrieved 2020/07/13.