3-Methylglutaric anhydride

Base Information

• Chemical Name: 3-Methylglutaric anhydride
• CAS No.: 4166-53-4
• Molecular Formula: C6H8O3
• Molecular Weight: 128.128
• Hs Code.: 2917190090
• European Community (EC) Number: 224-020-6
• DSSTox Substance ID: DTXSID90194487
• Nikkaji Number: J224.971E
• Wikidata: Q83067247
• Mol file: 4166-53-4.mol

Synonyms:3-Methylglutaric anhydride;4166-53-4;4-methyloxane-2,6-dione;4-Methyldihydro-2H-pyran-2,6(3H)-dione;MFCD00006683;.beta.-Methylglutaric anhydride;EINECS 224-020-6;2H-Pyran-2,6(3H)-dione, dihydro-4-methyl-;3-methyl glutaric anhydride;SCHEMBL287040;AMY3983;DTXSID90194487;3-Methylglutaric anhydride, 98%;4-methyl-dihydro-pyran-2,6-dione;BBL027601;STL183289;AKOS015955266;AS-63636;SY049353;4-Methyldihydro-2H-pyran-2,6(3H);-dione;CS-0152693;FT-0635169;M1010;4-Methyldihydro-2H-pyran-2,6(3H)-dione #;EN300-66372;D79206;A825625

Chemical Property of 3-Methylglutaric anhydride

Chemical Property:

• Appearance/Colour: WHITE CRYSTALLINE LOW MELTING SOLID
• Vapor Pressure: 0.00119mmHg at 25°C
• Melting Point: 40-45oC
• Refractive Index: 1.4585 (estimate)
• Boiling Point: 180-182 °C25 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 43.37000
• Density: 1.159g/cm³
• LogP: 0.48610
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 128.047344113
• Heavy Atom Count: 9
• Complexity: 134

Purity/Quality:

97% ^*data from raw suppliers

3-Methylglutaric Anhydride ^*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

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC(=O)OC(=O)C1
• Uses: 3-?Methylglutaric Anhydride is a reagent used in the synthesis of oxoeicosanoid receptor antagonists which are involved in mediating stimulatory effects on cell types involved in mediating immunity-based inflammatory reactions.

Technology Process of 3-Methylglutaric anhydride

There total 8 articles about 3-Methylglutaric 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: 90.0%

→ 3-methylglutaric anhydride (4166-53-4)

Guidance literature:

Reference yield: 79.0%

3-methyl glutaric acid (626-51-7) → 3-methylglutaric anhydride (4166-53-4)

Guidance literature:

With acetyl chloride; for 48h; Reflux;

DOI:10.1021/acs.joc.5b02177

Reference yield:

3-Methyl-glutarsaeure-mono--ester (4161-07-3) → 3-methylglutaric anhydride (4166-53-4)

Guidance literature:

With potassium chloride; sodium acetate; In 1,4-dioxane; at 30 ℃; Rate constant;

DOI:10.1021/ja01507a023

upstream raw materials:

methanol

3-methyl glutaric acid

3-methylpentanedial

malonic acid

Downstream raw materials:

3-Methyl-5-oxo-5-[5-(3-phenyl-propyl)-thiophen-2-yl]-pentanoic acid

3-Methyl-5-oxo-5-[5-(3-p-tolyl-propyl)-thiophen-2-yl]-pentanoic acid

3-Methyl-5-oxo-5-[5-(4-p-tolyl-butyl)-thiophen-2-yl]-pentanoic acid

diethyl 3-methylglutarate

Refernces

Studies on catalytic enantioselective total synthesis of caprazamycin B: Construction of the western zone

10.1021/jo301803h

The research focuses on the catalytic enantioselective total synthesis of the western zone of caprazamycin B, a novel lipo-nucleoside antibiotic with potent antimycobacterial activity against drug-susceptible and multidrug-resistant Mycobacterium tuberculosis strains. The purpose of this study is to develop a simple and efficient synthetic method for the western zone of caprazamycin B, utilizing two key catalytic asymmetric reactions: desymmetrization of 3-methylglutaric anhydride and a thioamide-aldol reaction. The synthesis involves the use of various chemicals, including (S)-Ni2-(Schiff base) complex as a catalyst for the desymmetrization step, and a combination of mesitylcopper, (R,R)-Ph-BPE, and 2,2,5,7,8-pentamethylchromanol as a catalyst for the thioamide-aldol reaction. Other chemicals used in the process include 3-methylglutaric anhydride, diallylthioamide, dimethylthioamide, and 2,3,4-tri-O-methyl-L-rhamnose, among others. The conclusions of the research indicate that the team successfully achieved a convergent synthesis of the western zone of caprazamycin B with good yield and enantioselectivity, laying the groundwork for further studies aimed at the catalytic enantioselective total synthesis of the entire caprazamycin B molecule.