Methyl 5-methylisoxazole-3-carboxylate

Base Information

• Chemical Name: Methyl 5-methylisoxazole-3-carboxylate
• CAS No.: 19788-35-3
• Molecular Formula: C6H7NO3
• Molecular Weight: 141.126
• Hs Code.: 29349990
• European Community (EC) Number: 243-311-9
• UNII: WKN4V23WWZ
• DSSTox Substance ID: DTXSID90173494
• Nikkaji Number: J110.589B
• Wikidata: Q72492874
• Mol file: 19788-35-3.mol

Synonyms:Methyl 5-methylisoxazole-3-carboxylate;19788-35-3;methyl 5-methyl-1,2-oxazole-3-carboxylate;3-Isoxazolecarboxylic acid, 5-methyl-, methyl ester;Methyl 5-methyl-3-isoxazolecarboxylate;WKN4V23WWZ;5-methylisoxazole-3-carboxylic acid methyl ester;EINECS 243-311-9;Methyl5-methylisoxazole-3-carboxylate;5-methyl-3-isoxazolecarboxylic acid methyl ester;5-methyl-isoxazole-3-carboxylic acid methyl ester;MFCD00015895;Methyl 5-methyl-3-isoxazole carboxylate;methyl-5-methyl-3-isoxazole carboxylate;UNII-WKN4V23WWZ;SCHEMBL1087642;DTXSID90173494;BCP32346;STR09388;STK426355;AKOS003278392;AM85653;CS-W018305;NG-0403;SDCCGMLS-0065953.P001;Methyl 5-methyl-3-isoxazolecarboxylate #;BB 0218309;FT-0628849;FT-0647821;EN300-15450;A813946;W-206457;Z17141189;F0001-0704

Chemical Property of Methyl 5-methylisoxazole-3-carboxylate

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0.064mmHg at 25°C
• Melting Point: 90-92 °C
• Refractive Index: 1.468
• Boiling Point: 230.875 °C at 760 mmHg
• PKA: -5.08±0.50(Predicted)
• Flash Point: 93.43 °C
• PSA: 52.33000
• Density: 1.179 g/cm³
• LogP: 0.76960
• Storage Temp.: 2-8°C
• XLogP3: 1
• 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% ^*data from raw suppliers

Methyl 5-methyl-3-isoxazolecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=NO1)C(=O)OC
• Uses: Methyl 5-Methyl-3-isoxazolecarboxylate is a related compound of Leflunomide (L322750), an antirheumatic compound used to treat rheumatoid arthritis and psoriatic arthritis. Leflunomide also inhibits dihydroorotate dehydrogenase.

Technology Process of Methyl 5-methylisoxazole-3-carboxylate

There total 4 articles about Methyl 5-methylisoxazole-3-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: 78.0%

methanol (67-56-1) + C28H39N5O7 → methyl 5-methylisoxazole-3-carboxylate (19788-35-3) + (2S,3R)-tert-butyl 4-(4-azidophenyl)-3-tert-butoxy-2-(5-methylisoxazole-3-carboxamido)butanoate

Guidance literature:

With potassium carbonate; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03118

Reference yield:

methyl 4-bromo-5-methyl-isoxazole-3-carboxylate (850832-54-1) + 1-methyl-2-(tri-n-butylstannyl)-1H-indole (157427-46-8) → methyl 5-methylisoxazole-3-carboxylate (19788-35-3) + methyl 5-methyl-4-(1-methylindol-2-yl)isoxazole-3-carboxylate

Guidance literature:

With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; cesium fluoride; In toluene; at 100 ℃; for 16h; Overall yield = 63 %; Overall yield = 210 mg; Sealed tube; Inert atmosphere;

DOI:10.1021/ol503479g

Reference yield:

methyl 2,4-dioxopentanoate (20577-61-1) → methyl 5-methylisoxazole-3-carboxylate (19788-35-3)

Guidance literature:

With sulfuric acid; hydroxylamine hydrochloride; sodium acetate; Yield given. Multistep reaction; 1.) water, reflux, 2 h, 2.) water, reflux, 3 h;

DOI:10.1016/0223-5234(96)88303-6

upstream raw materials:

methyl 2,4-dioxopentanoate

methyl 4-bromo-5-methyl-isoxazole-3-carboxylate

1-methyl-2-(tri-n-butylstannyl)-1H-indole

methanol

Downstream raw materials:

isocarboxazid

5-methylisoxazole-3-carboxylic acid hydrazide

5-methyl-isoxazole-3-carboxylic acid N'-(4-dimethylamino-benzyl)-hydrazide

5-methyl-isoxazole-3-carboxylic acid dimethylamide

Refernces

• 1、 Vickers, Clare F.,Silva, Ana P. G.,Chakraborty, Ajanta,Fernandez, Paulina,Kurepina, Natalia,Saville, Charis,Naranjo, Yandi,Pons, Miquel,Schnettger, Laura S.,Gutierrez, Maximiliano G.,Park, Steven,Kreiswith, Barry N.,Perlin, David S.,Thomas, Eric J.,Cavet, Jennifer S.,Tabernero, Lydia. "Structure-Based Design of MptpB Inhibitors That Reduce Multidrug-Resistant Mycobacterium tuberculosis Survival and Infection Burden in Vivo". . p. 8337 - 8352. Retrieved 2018/09/18.
• 2、 Dannhardt,Kiefer,Lambrecht,Laufer,Mutschler,Schweiger,Striegel. "Regioisomeric 3-, 4- and 5-aminomethyl isoxazoles: Synthesis and muscarinic activity". . p. 839 - 850. Retrieved 2007/10/03.