Isoxazole-5-carboxylic acid

Base Information

• Chemical Name: Isoxazole-5-carboxylic acid
• CAS No.: 21169-71-1
• Molecular Formula: C4H3NO3
• Molecular Weight: 113.073
• Hs Code.: 29349990
• European Community (EC) Number: 673-088-7
• DSSTox Substance ID: DTXSID70366185
• Nikkaji Number: J701.457K
• Wikidata: Q69757012
• Mol file: 21169-71-1.mol

Synonyms:Isoxazole-5-carboxylic acid;21169-71-1;1,2-oxazole-5-carboxylic Acid;5-isoxazolecarboxylic acid;ISOXAZOLE-5-CARBOXYLICACID;MFCD00156151;isoxazole-5-carboxylic;isoxazole 5-carboxylic acid;SCHEMBL112293;DTXSID70366185;MIIQJAUWHSUTIT-UHFFFAOYSA-N;Isoxazole-5-carboxylic acid, 97%;BBL100210;GEO-01628;STL553782;AKOS001042457;CS-W000637;PS-5358;SY018290;AM20090179;FT-0627541;EN300-06774;A815182;W-200213;Z56943419;F2158-0308;isoxazole-5-carbonyl chloride;Isoxazole-5-carboxylic Acid

Chemical Property of Isoxazole-5-carboxylic acid

Chemical Property:

• Appearance/Colour: slightly yellow powder
• Vapor Pressure: 0.000125mmHg at 25°C
• Melting Point: 144-148 °C(lit.)
• Refractive Index: 1.516
• Boiling Point: 321.2 °C at 760 mmHg
• PKA: 2.29±0.10(Predicted)
• Flash Point: 148.1 °C
• PSA: 63.33000
• Density: 1.449 g/cm³
• LogP: 0.37280
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Moisture Sensitive
• Water Solubility.: Slightly soluble in water.
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 113.011292958
• Heavy Atom Count: 8
• Complexity: 104

Purity/Quality:

99% ^*data from raw suppliers

5-IsoxazolecarboxylicAcid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(ON=C1)C(=O)O
• Uses: Reaction conditions were found to allow the exclusive formation of isoxazole-5-carboxylic acid derivatives by conjugate addition, in acidic medium, of hydroxylamine to β-alkoxyvinyl trichloromethyl ketone in synthesis and reactivity of isoxazoles. Isoxazole-5-carboxylic acid participates in the Synthesis and evaluation of acylguanidine FXa inhibitors. 1, 1, 1-trichloro-4-methoxy-3-penten-2-one postulated in the preparation of isoxazole-5-carboxylic acid from trichloroacetyl chloride, ethyl vinyl ether and hydroxylamine is developed in a fully saturated nitrogen atom theerefore there is no possibility of conjugation with 4- substituents.

Technology Process of Isoxazole-5-carboxylic acid

There total 11 articles about Isoxazole-5-carboxylic acid 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: 91.0%

ISOXAZOLE (288-14-2) + carbon dioxide (124-38-9,18923-20-1) → isoxazole-5-carboxylic acid (21169-71-1)

Guidance literature:

carbon dioxide; With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.25h; under 1125.11 Torr;

ISOXAZOLE; In tetrahydrofuran; at 20 ℃; for 12h; under 1125.11 Torr;

With hydrogenchloride; In tetrahydrofuran; water; regioselective reaction;

DOI:10.1021/ja103429q

Reference yield: 91.0%

→ isoxazole-5-carboxylic acid (21169-71-1)

Guidance literature:

With [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(OH)]; potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;

With hydrogenchloride; In tetrahydrofuran; water;

Reference yield: 85.0%

(3E)-1,1,1-trichloro-4-ethoxybut-3-en-2-one (59938-07-7) → isoxazole-5-carboxylic acid (21169-71-1)

Guidance literature:

With sulfuric acid; hydroxylamine hydrochloride; at 40 - 100 ℃; for 12h;

DOI:10.1016/S0040-4039(99)02047-X

upstream raw materials:

5-(hydroxymethyl)isoxazole

1-(isoxazole-5-yl)ethanone

isoxazole-5-carbaldehyde oxime

5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazole

Downstream raw materials:

N-Methoxy-N-methyl-5-isoxazolecarboxamide

C₂₄H₃₀N₆O₄

C₂₄H₃₀N₆O₅

C₂₂H₂₆N₆O₄

Refernces

• 1、 -. "CARBOXYLATION CATALYSTS". Paragraph 0093. . Retrieved 2013/04/13.
• 2、 Martins, Marcos A. P.,Flores, Alex F. C.,Bastos, Giovani P.,Sinhorin, Adilson,Bonacorso, Helio G.,Zanatta, Nilo. "A convenient one-pot synthesis of 5-carboxyisoxazoles: Trichloromethyl group as a carboxyl group precursor". . p. 293 - 297. Retrieved 2007/10/03.