5-Cyclopropylisoxazole-3-carboxylic acid

Base Information

• Chemical Name: 5-Cyclopropylisoxazole-3-carboxylic acid
• CAS No.: 110256-15-0
• Molecular Formula: C7H7 N O3
• Molecular Weight: 153.137
• Hs Code.: 2934999090
• European Community (EC) Number: 625-717-1
• DSSTox Substance ID: DTXSID40360231
• Wikidata: Q72460934
• ChEMBL ID: CHEMBL4128366
• Mol file: 110256-15-0.mol

Synonyms:5-Cyclopropylisoxazole-3-carboxylic acid;110256-15-0;5-cyclopropyl-1,2-oxazole-3-carboxylic acid;5-Cyclopropyl-isoxazole-3-carboxylic acid;5-cyclopropyl-3-isoxazolecarboxylic acid;3-Isoxazolecarboxylic acid, 5-cyclopropyl-;MFCD05668325;3-Isoxazolecarboxylicacid, 5-cyclopropyl-;SCHEMBL841342;CHEMBL4128366;DTXSID40360231;OWMVXHFZCCPOTD-UHFFFAOYSA-N;HMS1695C07;BBL022976;STK352048;AKOS000263472;CS-W008513;AS-39493;SY014190;BB 0260193;FT-0731267;EN300-24688;5-Cyclopropyl-1,2-isoxazole-3-carboxylic acid;5-Cyclopropylisoxazole-3-carboxylic acid, 95%;A898908;J-002410;F2135-0510

Chemical Property of 5-Cyclopropylisoxazole-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 9.48E-06mmHg at 25°C
• Melting Point: 96-100 °C(lit.)
• Refractive Index: 1.586
• Boiling Point: 358.1°C at 760 mmHg
• PKA: 3.46±0.10(Predicted)
• Flash Point: 170.4°C
• PSA: 63.33000
• Density: 1.445
• LogP: 1.25020
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 153.042593085
• Heavy Atom Count: 11
• Complexity: 179

Purity/Quality:

97% ^*data from raw suppliers

5-Cyclopropylisoxazole-3-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C2=CC(=NO2)C(=O)O
• Uses: 5-Cyclopropylisoxazole-3-carboxylic Acid is a compound that has been used in the discovery, design and synthesis of a selective S1P3 receptor allosteric agonist (N,N-Dicyclohexyl-5-propylisoxazole-3-carboxamide).

Technology Process of 5-Cyclopropylisoxazole-3-carboxylic acid

There total 6 articles about 5-Cyclopropylisoxazole-3-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: 100.0%

ethyl 5-cyclopropylisoxazole-3-carboxylate (21080-81-9) → 5-cyclopropylisoxazole-3-carboxylic acid (110256-15-0)

Guidance literature:

With sodium hydroxide; In ethanol; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b01522

Reference yield:

Cyclopropyl methyl ketone (765-43-5) → 5-cyclopropylisoxazole-3-carboxylic acid (110256-15-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 12 h / Inert atmosphere

2.1: hydroxylamine hydrochloride / methanol / 2 h / Reflux; Inert atmosphere

3.1: sodium hydroxide / ethanol / 2 h / 0 °C / Inert atmosphere

With hydroxylamine hydrochloride; sodium hydride; sodium hydroxide; In tetrahydrofuran; methanol; ethanol;

DOI:10.1021/acs.jmedchem.5b01522

Reference yield:

ethyl 4-cyclopropyl-2,4-dioxobutanoate (21080-80-8) → 5-cyclopropylisoxazole-3-carboxylic acid (110256-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydroxylamine hydrochloride / ethanol; water / 2 h / 20 - 80 °C

2: sodium hydroxide / water / 1 h / 20 °C

With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; water;

upstream raw materials:

ethyl 5-cyclopropylisoxazole-3-carboxylate

ethyl (3Z)-4-cyclopropyl-4-hydroxy-2-oxo-3-butenoate

Cyclopropyl methyl ketone

ethyl 4-cyclopropyl-2,4-dioxobutanoate

Downstream raw materials:

C₁₃H₁₁ClN₂O₂

5-cyclopropyl-isoxazole-3-carboxylic acid (1-{4-[3-chloro-2-(2-methyl-2H-tetrazol-5-yl)-indol-1-yl]-benzylcarbamoyl}-cyclopropyl)-amide

N,N-Dicyclohexyl-5-cyclopropyl-3-isoxazolecarboxamide