2-(Benzo[d]isoxazol-3-yl)-2-bromoacetic acid

Base Information

• Chemical Name: 2-(Benzo[d]isoxazol-3-yl)-2-bromoacetic acid
• CAS No.: 37924-67-7
• Molecular Formula: C9H6 Br N O3
• Molecular Weight: 256.056
• Hs Code.: 29349990
• European Community (EC) Number: 609-488-5
• DSSTox Substance ID: DTXSID301280371
• Mol file: 37924-67-7.mol

Synonyms:37924-67-7;2-(benzo[d]isoxazol-3-yl)-2-bromoacetic acid;Alpha-bromo-1,2-benzisoxazole-3-acetic acid;2-(1,2-benzoxazol-3-yl)-2-bromoacetic acid;SCHEMBL692254;SCHEMBL14185644;GOEZDVVTYIWCAJ-UHFFFAOYSA-N;DTXSID301280371;MFCD18909732;AKOS015950786;AS-44191;2-(benzo[d]isoxazol-3-yl)-2-bromoaceticacid;J-506216;F1967-2584

Chemical Property of 2-(Benzo[d]isoxazol-3-yl)-2-bromoacetic acid

Chemical Property:

• Melting Point: 123-126°C
• Boiling Point: 394.9±27.0 °C(Predicted)
• PKA: 2.03±0.30(Predicted)
• PSA: 63.33000
• Density: 1.816±0.06 g/cm3(Predicted)
• LogP: 1.45490
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 254.95311
• Heavy Atom Count: 14
• Complexity: 236

Purity/Quality:

98% ^*data from raw suppliers

2-(Benzo[d]isoxazol-3-yl)-2-bromoaceticacid 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=NO2)C(C(=O)O)Br
• Uses: α-Bromo-1,2-benzisoxazole-3-acetic Acid is an intermediate in the synthesis of Zonisamide (Z700000); Sulfonamide antiseizure agent; blocks repetitive firing of voltagesensitive sodium channels and reduces voltage-sensitive T-type calcium currents. Heterocyclic methanesulfonide with anticonvulsant properties. The compound is under investigation for potential therapeutic use as an antiepileptic drug. Anticonvulsant. Neuroprotective & Neuroresearch Product.

Technology Process of 2-(Benzo[d]isoxazol-3-yl)-2-bromoacetic acid

There total 3 articles about 2-(Benzo[d]isoxazol-3-yl)-2-bromoacetic 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: 85.0%

2-(benzo[d]isoxazol-3-yl)acetic acid (4865-84-3) → α-bromo-1,2-benzisoxazole-3-acetic acid (37924-67-7)

Guidance literature:

With bromine; acetic acid; at 20 ℃; for 6.5h;

Reference yield:

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) → α-bromo-1,2-benzisoxazole-3-acetic acid (37924-67-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hydroxyamino hydrochloride; sodium hydroxide / ethanol / 16 h / 81 °C

2: bromine; acetic acid / 6.5 h / 20 °C

With hydroxyamino hydrochloride; bromine; acetic acid; sodium hydroxide; In ethanol;

DOI:10.1021/acschemneuro.1c00846

Reference yield:

4‐hydroxycoumarin (22105-09-5) → α-bromo-1,2-benzisoxazole-3-acetic acid (37924-67-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; hydroxylamine hydrochloride / ethanol / 16 h / 80 °C

2: acetic acid; bromine / 6.5 h / 20 °C

With hydroxylamine hydrochloride; bromine; acetic acid; sodium hydroxide; In ethanol;

upstream raw materials:

2-(benzo[d]isoxazol-3-yl)acetic acid

4‐hydroxycoumarin

4-hydroxy[1]benzopyran-2-one

Downstream raw materials:

(1,2-benzisoxazol-3-yl)phenoxyacetic acid

1,2-benzisoxazole-3-carboxaldehyde

3-bromomethyl-1,2-benzisoxazole

methyl 3-(2-acetoxyphenyl)-2-phenoxy-2H-azirine-2-carboxylate

Refernces

• 1、 Dong, Shiyang,Huang, Xiang,Liu, Hua,Quan, Hexiu,Wan, Pingnan,Wang, Tiantian,Wang, Zengcai,Wang, Zengtao. "Design, Synthesis, and Evaluation of Novel Benzo[ d]isoxazole Derivatives as Anticonvulsants by Selectively Blocking the Voltage-Gated Sodium Channel NaV1.1". . . Retrieved 2022/03/15.