Ethyl 5-amino-3-methyl-1,2-oxazole-4-carboxylate

Base Information

• Chemical Name: Ethyl 5-amino-3-methyl-1,2-oxazole-4-carboxylate
• CAS No.: 25786-72-5
• Molecular Formula: C7H10N2O3
• Molecular Weight: 170.17
• Hs Code.: 29349990
• DSSTox Substance ID: DTXSID40351922
• Wikidata: Q72472460
• Mol file: 25786-72-5.mol

Synonyms:25786-72-5;ethyl 5-amino-3-methyl-1,2-oxazole-4-carboxylate;ethyl 5-amino-3-methylisoxazole-4-carboxylate;5-Amino-3-methyl-isoxazole-4-carboxylic acid ethyl ester;Ethyl 5-amino-3-methyl-4-isoxazolecarboxylate;4-Isoxazolecarboxylic acid, 5-amino-3-methyl-, ethyl ester;SCHEMBL15525136;DTXSID40351922;ULIKRPZEQZFBPS-UHFFFAOYSA-N;HMS1620B10;BBL030106;MFCD03820571;STK772678;AKOS001121155;AS-66846;FT-0687884;EN300-13563;ethyl 5-amino-3-methyl-4-isoxazole carboxylate;W-202088;Z90667557;F2124-0455;Isoxazole-4-carboxylic acid, 5-amino-3-methyl-, ethyl ester

Chemical Property of Ethyl 5-amino-3-methyl-1,2-oxazole-4-carboxylate

Chemical Property:

• Vapor Pressure: 0.00256mmHg at 25°C
• Melting Point: 133-135 °C
• Refractive Index: 1.52
• Boiling Point: 287 °C at 760 mmHg
• PKA: -2.37±0.10(Predicted)
• Flash Point: 127.3 °C
• PSA: 78.35000
• Density: 1.229 g/cm³
• LogP: 1.32310
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 170.06914219
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

NLT 98% ^*data from raw suppliers

Ethyl5-Amino-3-methylisoxazole-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(ON=C1C)N
• Uses: Ethyl 5-Amino-3-methylisoxazole-4-carboxylate is an intermediate used to preapre isoxazolopyrimidone or isoxazolotriazinone compounds as herbicides and hepatic antitumor agents.

Technology Process of Ethyl 5-amino-3-methyl-1,2-oxazole-4-carboxylate

There total 6 articles about Ethyl 5-amino-3-methyl-1,2-oxazole-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: 20.0%

Sodium; (E)-1-cyano-1-ethoxycarbonyl-propen-2-olate → 5-amino-3-methyl-4-isoxazolecarboxylic acid ethyl ester (25786-72-5)

Guidance literature:

With hydroxylamine hydrochloride; In water; for 3h; Heating;

DOI:10.1002/jhet.5570230414

Reference yield:

ethyl 2-cyano-3-ethoxybut-2-enoate (35260-93-6,932750-29-3) → 5-amino-3-methyl-4-isoxazolecarboxylic acid ethyl ester (25786-72-5)

Guidance literature:

With hydroxylamine hydrochloride; sodium methylate; In ethanol;

DOI:10.1007/BF00909279

Reference yield:

5-methylisoxazole-4-carboxylic acid ethyl ester (51135-73-0) → 5-amino-3-methyl-4-isoxazolecarboxylic acid ethyl ester (25786-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH

2: 20 percent / hydroxylamine hydrochloride / H₂O / 3 h / Heating

With sodium hydroxide; hydroxylamine hydrochloride; In water;

DOI:10.1002/jhet.5570230414

upstream raw materials:

ethyl 2-cyanoacetoacetate

ethyl 2-cyano-3-ethoxybut-2-enoate

acetimidoyl chloride

ethyl 2-cyanoacetate

Downstream raw materials:

3-methyl-5-phenoxymethylthiophosphorylamino-4-ethoxycarbonylisoxazole

3-methyl-5-di(phenoxymethylthiophosphoryl)amino-4-ethoxycarbonylisoxazole

3-methylisoxazole-4-carboxylic acid ethyl ester

C₁₂H₈ClN₃O₃

Refernces

• 1、 Alberola,Antolin,Gonzalez,et al.. "Base-induced ring cleavage of 4-functionalized-3-unsubstituted isoxazoles. Synthesis of 5-aminoazoles and 4-cyanoazoles [1]". . p. 1035 - 1038. Retrieved 2007/10/02.