3-Amino-1,2-benzisoxazole-6-carbonitrile

Base Information

• Chemical Name: 3-Amino-1,2-benzisoxazole-6-carbonitrile
• CAS No.: 229623-53-4
• Molecular Formula: C₈H₅N₃O
• Molecular Weight: 159.147
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60466446
• Nikkaji Number: J1.130.619E
• Wikidata: Q82293011
• Mol file: 229623-53-4.mol

Synonyms:229623-53-4;3-Amino-1,2-benzisoxazole-6-carbonitrile;3-aminobenzo[d]isoxazole-6-carbonitrile;3-amino-1,2-benzoxazole-6-carbonitrile;1,2-Benzisoxazole-6-carbonitrile, 3-amino-;SCHEMBL3507599;DTXSID60466446;OCJIURFDSUKEMM-UHFFFAOYSA-N;3-amino-6-cyano-1,2-benzisoxazole;MFCD09907912;AKOS006313353;FS-2788;3-amino-1, 2-benzoxazole-6-carbonitrile;3-amino-benzo[d]isoxazole-6-carbonitrile;FT-0646042;1,2-Benzisoxazole-6-carbonitrile,3-amino-(9CI);A878369

Chemical Property of 3-Amino-1,2-benzisoxazole-6-carbonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.683
• Boiling Point: 408.53°C at 760 mmHg
• Flash Point: 200.872°C
• PSA: 75.84000
• Density: 1.411g/cm³
• LogP: 1.86288
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 159.043261791
• Heavy Atom Count: 12
• Complexity: 222

Purity/Quality:

98%min ^*data from raw suppliers

3-Amino-1,2-benzisoxazole-6-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1C#N)ON=C2N

Technology Process of 3-Amino-1,2-benzisoxazole-6-carbonitrile

There total 5 articles about 3-Amino-1,2-benzisoxazole-6-carbonitrile 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:

2-fluoroterephthalonitrile (1897-53-6) + acetone oxime (127-06-0) → 6-cyano-3-amino-1,2-benzisoxazole (229623-53-4,201157-76-8)

Guidance literature:

acetone oxime; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.333333h;

2-fluoroterephthalonitrile; In tetrahydrofuran; at 20 - 60 ℃; for 2.5h;

With hydrogenchloride; sodium carbonate; more than 3 stages;

Reference yield:

2-fluoroterephthalonitrile (1897-53-6) → 6-cyano-3-amino-1,2-benzisoxazole (229623-53-4,201157-76-8)

Guidance literature:

With acetylhydroxamic acid; potassium tert-butylate; In N,N-dimethyl-formamide; at 20 - 70 ℃; for 39h;

DOI:10.1016/S0960-894X(02)00585-1

Reference yield:

4-bromo-6-fluorobenzonitrile (105942-08-3) → 6-cyano-3-amino-1,2-benzisoxazole (229623-53-4,201157-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylformamide / Heating

2: CH₃CONHOH; KO-t-Bu / dimethylformamide / 39 h / 20 - 70 °C

With acetylhydroxamic acid; potassium tert-butylate; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(02)00585-1

upstream raw materials:

2-fluoroterephthalonitrile

4-bromo-6-fluorobenzonitrile

acetone oxime

Downstream raw materials:

6-aminomethyl-benzo[d]isoxazol-3-ylamine

Refernces

• 1、 Cui, Jingrong Jean,Araldi, Gian-Luca,Reiner, John E.,Reddy, Komandla Malla,Kemp, Scott J.,Ho, Jonathan Z.,Siev, Daniel V.,Mamedova, Lala,Gibson, Tony S.,Gaudette, John A.,Minami, Nathaniel K.,Anderson, Susanne M.,Bradbury, Annette E.,Nolan, Thomas G.,Semple. "Non-covalent thrombin inhibitors featuring P3-heterocycles with P1-bicyclic arginine surrogates". . p. 2925 - 2930. Retrieved 2007/10/03.
• 2、 Lepore, Salvatore D.,Wiley, Michael R.. "Use of the Kaiser Oxime Resin in the Solid-Phase Synthesis of 3-Aminobenzisoxazoles". . p. 4547 - 4550. Retrieved 2007/10/03.