Methyl 5-methyloxazole-4-carboxylate

Base Information

• Chemical Name: Methyl 5-methyloxazole-4-carboxylate
• CAS No.: 41172-57-0
• Molecular Formula: C6H7NO3
• Molecular Weight: 141.126
• Hs Code.: 2934999090
• European Community (EC) Number: 689-072-8
• DSSTox Substance ID: DTXSID50504861
• Nikkaji Number: J2.036.203K
• Wikidata: Q82359627
• Mol file: 41172-57-0.mol

Synonyms:Methyl 5-methyloxazole-4-carboxylate;41172-57-0;Methyl 5-methyl-1,3-oxazole-4-carboxylate;Methyl 5-methyl-4-oxazolecarboxylate;5-methyl-4-oxazolecarboxylic acid methyl ester;MFCD08689502;SCHEMBL2143331;DTXSID50504861;UMYOVEXLUCPUAU-UHFFFAOYSA-N;AMY18950;Methyl 5-methyoxazole-4-carboxylate;AKOS006346201;PS-4901;CS-0153622;FT-0646205;A825456;J-522497

Chemical Property of Methyl 5-methyloxazole-4-carboxylate

Chemical Property:

• Vapor Pressure: 0.583mmHg at 25°C
• Melting Point: 45-48°C
• Refractive Index: 1.468
• Boiling Point: 188.981 °C at 760 mmHg
• PKA: -1.08±0.10(Predicted)
• Flash Point: 68.094 °C
• PSA: 52.33000
• Density: 1.18 g/cm³
• LogP: 0.76960
• Storage Temp.: Keep Cold
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 141.042593085
• Heavy Atom Count: 10
• Complexity: 137

Purity/Quality:

98%min ^*data from raw suppliers

5-Methyl-4-oxazolecarboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N=CO1)C(=O)OC
• Uses: 5-Methyl-4-oxazolecarboxylic Acid Methyl Ester is used as a reagent in the syntheses of substituted oxazolyl-1,3,4-thiadiazoles, -1,3,4-oxadiazoles, and -1,2,4-triazoles. Also used as a reagent in the synthesis of Muscoride A.

Technology Process of Methyl 5-methyloxazole-4-carboxylate

There total 4 articles about Methyl 5-methyloxazole-4-carboxylate 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: 93.0%

isocyanoacetic acid methyl ester (39687-95-1) + acetic anhydride (108-24-7) → 5-Methyloxazol-4-carbonsaeure-methylester (41172-57-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ja306062c

Reference yield: 45.0%

N-(1-methoxycarbonyl-2-oxopropyl)formamide (706822-01-7) → 5-Methyloxazol-4-carbonsaeure-methylester (41172-57-0)

Guidance literature:

With iodine; triethylamine; triphenylphosphine; In dichloromethane; for 16h;

DOI:10.1016/j.tet.2004.03.037

Reference yield:

2-Diazo-3-oxo-butyric acid methyl ester (24762-04-7) → 5-Methyloxazol-4-carbonsaeure-methylester (41172-57-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / Rh₂(OAc)4 / 1,2-dichloro-ethane / Heating

2: 45 percent / triphenylphosphine; iodine; triethylamine / CH₂Cl₂ / 16 h

With iodine; triethylamine; triphenylphosphine; dirhodium tetraacetate; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/j.tet.2004.03.037

upstream raw materials:

isocyanoacetic acid methyl ester

acetic anhydride

acetyl chloride

N-(1-methoxycarbonyl-2-oxopropyl)formamide

Downstream raw materials:

5-methyloxazole-4-carboxylic acid

C₁₃H₁₁NO₄

(E)-methyl 2-(3,4-dimethoxystyryl)-5-methyloxazole-4-carboxylate

4-hydroxymethyl-5-methyloxazole

Refernces

• 1、 Yang, Ke,Zhang, Cheng,Wang, Peng,Zhang, Yan,Ge, Haibo. "Nickel-catalyzed decarboxylative acylation of heteroarenes by sp 2 C-H functionalization". supporting information. p. 7241 - 7244. Retrieved 2014/06/23.
• 2、 Meng, Lingkui,Kamada, Yuko,Muto, Kei,Yamaguchi, Junichiro,Itami, Kenichiro. "C-H alkenylation of azoles with enols and esters by nickel catalysis". supporting information. p. 10048 - 10051. Retrieved 2013/10/01.