Benzo[d]isoxazole-3-carboxylic Acid

Base Information

• Chemical Name: Benzo[d]isoxazole-3-carboxylic Acid
• CAS No.: 28691-47-6
• Molecular Formula: C8H5NO3
• Molecular Weight: 163.133
• Hs Code.: 2934999090
• European Community (EC) Number: 820-845-6
• DSSTox Substance ID: DTXSID70370727
• Nikkaji Number: J598.432G
• Wikidata: Q72445568
• Mol file: 28691-47-6.mol

Synonyms:Benzo[d]isoxazole-3-carboxylic Acid;28691-47-6;1,2-benzoxazole-3-carboxylic acid;1,2-benzisoxazole-3-carboxylic acid;MFCD06659786;benzo(d)isoxazole-3-carboxylic acid;benzisoxazole-3-carboxylic;3-carboxy-l,2-benzisoxazole;3-benzisoxazolecarboxylic acid;3-carboxy-1,2-benzisoxazole;SCHEMBL496601;DTXSID70370727;VPYXATIIMHQAPR-UHFFFAOYSA-N;Benzo[d]isoxazole-3-carboxylicAcid;AMY12173;BBL102791;STL556598;AKOS006228690;AB26306;CS-W005473;GS-4147;FT-0701778;EN300-147407;1,2-benzisoxazole-3-carboxylic acid, AldrichCPR;A847375;J-519727

Chemical Property of Benzo[d]isoxazole-3-carboxylic Acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 145-146 °C
• Refractive Index: 1.661
• Boiling Point: 379.772 °C at 760 mmHg
• PKA: 2.32±0.10(Predicted)
• Flash Point: 183.48 °C
• PSA: 63.33000
• Density: 1.455 g/cm³
• LogP: 1.52600
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 163.026943022
• Heavy Atom Count: 12
• Complexity: 195

Purity/Quality:

98%min ^*data from raw suppliers

Benzo[d]isoxazole-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=NO2)C(=O)O
• Uses: Benzo[d]isoxazole-3-carboxylic acid is a metabolite of zonisamide; an anticonvulsant medication.

Technology Process of Benzo[d]isoxazole-3-carboxylic Acid

There total 6 articles about Benzo[d]isoxazole-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: 57.0%

ethyl 1,2-benzisoxazole-3-carboxylate (57764-49-5) → benzisoxazole-3-carboxylic acid (28691-47-6)

Guidance literature:

With sulfuric acid;

Reference yield:

hydroxyimino-(2-nitro-phenyl)-acetic acid ethyl ester (57764-48-4) → benzisoxazole-3-carboxylic acid (28691-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / bis-(2-methoxy-ethyl) ether

2: 70percent H₂SO₄

With sulfuric acid; sodium hydride; In diethylene glycol dimethyl ether;

DOI:10.1021/jm00041a009

Reference yield:

2-(2-nitrophenyl)acetic acid (3740-52-1) → benzisoxazole-3-carboxylic acid (28691-47-6)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂SO₄ / toluene / Heating

2: isoamyl nitrite, NaOEt / ethanol

3: NaH / bis-(2-methoxy-ethyl) ether

4: 70percent H₂SO₄

With sulfuric acid; sodium ethanolate; sodium hydride; isopentyl nitrite; In ethanol; diethylene glycol dimethyl ether; toluene;

DOI:10.1021/jm00041a009

upstream raw materials:

methyl benzo[d]isoxazole-3-carboxylate

ethyl 1,2-benzisoxazole-3-carboxylate

2-(2-nitrophenyl)acetic acid

ethyl 2-nitrophenylacetate

Downstream raw materials:

salicylonitrile

carbon dioxide

2-[(benzo[d]isoxazole-3-carbonyl)-amino]-5-bromo-benzoic acid methyl ester

2-[3-(2-benzo[d] isoxazol-3-ylimidazo[1,2-a]pyridin-6-yl)phenyl]propan-2-ol

Refernces

• 1、 Qiao, Lixin,Choi, Sungwoon,Case, April,Gainer, Thomas G.,Seyb, Kathleen,Glicksman, Marcie A.,Lo, Donald C.,Stein, Ross L.,Cuny, Gregory D.. "Structure-activity relationship study of EphB3 receptor tyrosine kinase inhibitors". supporting information; experimental part. p. 6122 - 6126. Retrieved 2010/06/16.
• 2、 -. "INDOLES, 1H-INDAZOLES, 1,2-BENZISOXAZOLES, AND 1,2-BENZISOTHIAZOLES, AND PREPARATION AND USES THEREOF". Page/Page column 44-45. . Retrieved 2008/06/13.