4-Amino-2-fluoro-5-iodobenzonitrile

Base Information

• Chemical Name: 4-Amino-2-fluoro-5-iodobenzonitrile
• CAS No.: 380241-60-1
• Molecular Formula: C₇H₄FIN₂
• Molecular Weight: 262.025
• Hs Code.: 2922390090
• DSSTox Substance ID: DTXSID40451395
• Wikidata: Q82271399
• Mol file: 380241-60-1.mol

Synonyms:4-AMINO-2-FLUORO-5-IODOBENZONITRILE;380241-60-1;MFCD09909321;AB3025;SCHEMBL20595008;DTXSID40451395;AS-44675;SY236670;CS-0068963;A918813

Chemical Property of 4-Amino-2-fluoro-5-iodobenzonitrile

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 261.94032
• Heavy Atom Count: 11
• Complexity: 188

Purity/Quality:

99% ^*data from raw suppliers

4-Amino-2-fluoro-5-iodobenzonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1I)N)F)C#N

Technology Process of 4-Amino-2-fluoro-5-iodobenzonitrile

There total 6 articles about 4-Amino-2-fluoro-5-iodobenzonitrile 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: 33.0%

4-amino-2-fluorobenzonitrile (53312-80-4) → 4-amino-2-fluoro-5-iodobenzonitrile (380241-60-1)

Guidance literature:

With N-iodo-succinimide; acetic acid; at 20 ℃; for 2h;

DOI:10.1021/jm010244+

Reference yield:

2-fluoro-4-nitrobenzonitrile (34667-88-4) → 4-amino-2-fluoro-5-iodobenzonitrile (380241-60-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / 10percent Pd/C / methanol / 8 h / 760.05 Torr

2: 33 percent / NIS; AcOH / 2 h / 20 °C

With N-iodo-succinimide; hydrogen; acetic acid; 10percent Pd/C; In methanol;

DOI:10.1021/jm010244+

Reference yield:

2-fluoro-4-nitrotoluene (1427-07-2) → 4-amino-2-fluoro-5-iodobenzonitrile (380241-60-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 52 percent / aq. CrO₃; H₂SO₄; AcOH / 20 - 100 °C

2: (COCl)2; DMF / tetrahydrofuran / 3 h / 0 - 20 °C

3: 15.5 g / NH₃ gas / tetrahydrofuran / 2.5 h / 0 °C

4: 14.7 g / Et₃N; (CF₃CO)2O / tetrahydrofuran / 16 h / 20 °C

5: 100 percent / H₂ / 10percent Pd/C / methanol / 8 h / 760.05 Torr

6: 33 percent / NIS; AcOH / 2 h / 20 °C

With chromium(VI) oxide; N-iodo-succinimide; oxalyl dichloride; sulfuric acid; ammonia; hydrogen; acetic acid; triethylamine; N,N-dimethyl-formamide; trifluoroacetic anhydride; 10percent Pd/C; In tetrahydrofuran; methanol;

DOI:10.1021/jm010244+

upstream raw materials:

4-amino-2-fluorobenzonitrile

2-fluoro-4-nitrobenzonitrile

2-fluoro-4-nitrotoluene

2-fluoro-4-nitrobenzoic acid

Downstream raw materials:

(4-cyano-2-iodo-5-fluorophenyl)carbamic acid tert-butyl ester

6-fluoro-1H-indole-5-carbonitrile

Refernces

• 1、 -. "SUBSTITUTED 5-CYANOINDOLE COMPOUNDS AND USES THEREOF". Paragraph 00217. . Retrieved 2019/01/10.
• 2、 Mackman,Katz,Breitenbucher,Hui,Verner,Luong,Liu,Sprengeler. "Exploiting subsite S1 of trypsin-like serine proteases for selectivity: Potent and selective inhibitors of urokinase-type plasminogen activator". . p. 3856 - 3871. Retrieved 2007/10/03.