Methylsuccinic anhydride

Base Information

• Chemical Name: Methylsuccinic anhydride
• CAS No.: 4100-80-5
• Deprecated CAS: 90866-24-3
• Molecular Formula: C5H6O3
• Molecular Weight: 114.101
• Hs Code.: 2917190090
• European Community (EC) Number: 223-870-5
• NSC Number: 65437,43978
• DSSTox Substance ID: DTXSID10871900
• Nikkaji Number: J80.746J
• Wikidata: Q27159753
• Mol file: 4100-80-5.mol

Synonyms:Methylsuccinic anhydride;4100-80-5;3-methyldihydrofuran-2,5-dione;Pyrotartaric anhydride;3-Methylsuccinic anhydride;3-methyloxolane-2,5-dione;2,5-Furandione, dihydro-3-methyl-;2-Methylsuccinic anhydride;Methylsuccinicanhydride;Succinic anhydride, methyl-;EINECS 223-870-5;MFCD00005527;NSC 65437;AI3-11208;3-Methyldihydrofuran-2,5-dione;1-Pyrotartaric anhydride;methyl succinic anhydride;methyl-succinic anhydride;2, dihydro-3-methyl-;methylsuccinic acid anhydride;NCIOpen2_000303;SCHEMBL135300;Methylsuccinic anhydride, 98%;CHEBI:87587;3-methyl-dihydrofuran-2,5-dione;DTXSID10871900;3-Methyldihydro-2,5-furandione #;CS-Z0015;NSC43978;NSC65437;NSC-43978;NSC-65437;AKOS009157111;3,4-Dihydro-3-methyl-2,5-furandione;SY113513;A6823;FT-0635128;FT-0772919;EN300-51761;Q27159753

Chemical Property of Methylsuccinic anhydride

Chemical Property:

• Vapor Pressure: 0.0411mmHg at 25°C
• Melting Point: 33-35 °C(lit.)
• Refractive Index: 1.452
• Boiling Point: 239 °C at 760 mmHg
• Flash Point: 108.2 °C
• PSA: 43.37000
• Density: 1.23 g/cm³
• LogP: 0.09600
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 114.031694049
• Heavy Atom Count: 8
• Complexity: 139

Purity/Quality:

99% ^*data from raw suppliers

Methylsuccinic anhydride 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC(=O)OC1=O
• Uses: 2-Methylsuccinic Anhydride is reported to be a pollutant which occurs as partially oxidized organic component in urban aerosol.

Technology Process of Methylsuccinic anhydride

There total 33 articles about Methylsuccinic anhydride 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: 96.0%

2-methylbutanedioic acid (498-21-5,636-60-2) → 2-methylsuccinic anhydride (4100-80-5)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In toluene; for 3h; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2017.06.089

Reference yield: 96.0%

((C6H5)2PCH2CH2P(C6H5)2)NiCH2CH(CH3)COO → Ni(CO)2{1,2-bis(diphenylphosphino)ethane} (15793-01-8) + 2-methylsuccinic anhydride (4100-80-5)

Guidance literature:

With carbon monoxide; In dichloromethane; Schlenk tube contg. CH2Cl2 soln. of nickel complex evacuated and 1 atm of CO introduced; analyzed by GLC, GC-mass, and IR;

DOI:10.1246/bcsj.57.2741

Reference yield: 95.0%

4-methyloxetan-2-one (3068-88-0,32082-74-9,36536-46-6,65058-82-4) + carbon monoxide (201230-82-2) → 2-methylsuccinic anhydride (4100-80-5)

Guidance literature:

With ({1,2-di[(2-OH-3,5-di-tBu)PhCH=N]Ph}Al[THF]2)⁺[Co(CO)4]^-; In toluene; at 55 ℃; for 24h; under 10343 Torr;

DOI:10.1021/ja048946m

upstream raw materials:

2-methylbutanedioic acid

citraconic acid anhydride

(2R,5S)-menthone

itaconic acid anhydride

Downstream raw materials:

methyl 2-methylsuccinate

3-(Acetyl-methyl-amino)-5-(3-carboxy-2-methyl-propionylamino)-2,4,6-triiodo-benzoic acid

2-Acetyl-4-methyl-cyclopentan-1.3-dion

metbufene

Refernces

• 1、 Li, Wen-Bing,Liu, Ye,Lu, Xiao-Bing,Yang, Jin-Chuang,Yang, Jun. "Carbonylative Polymerization of Epoxides Mediated by Tri-metallic Complexes: A Dual Catalysis Strategy for Synthesis of Biodegradable Polyhydroxyalkanoates". supporting information. . Retrieved 2022/01/20.
• 2、 Podgórski, Maciej,Mavila, Sudheendran,Huang, Sijia,Spurgin, Nathan,Sinha, Jasmine,Bowman, Christopher N.. "Thiol–Anhydride Dynamic Reversible Networks". supporting information. p. 9345 - 9349. Retrieved 2020/04/07.