Isoindoline-5-carbonitrile

Base Information

• Chemical Name: Isoindoline-5-carbonitrile
• CAS No.: 263888-58-0
• Molecular Formula: C9H8 N2
• Molecular Weight: 144.176
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80591961
• Nikkaji Number: J1.526.246J
• Wikidata: Q82485834
• Mol file: 263888-58-0.mol

Synonyms:ISOINDOLINE-5-CARBONITRILE;263888-58-0;2,3-DIHYDRO-1H-ISOINDOLE-5-CARBONITRILE;MFCD08234858;5-Cyanoisoindoline;1H-ISOINDOLE-5-CARBONITRILE, 2,3-DIHYDRO-;SCHEMBL330686;DTXSID80591961;NHIKDNWKXUBYHV-UHFFFAOYSA-N;5-Cyano-2,3-dihydro-1H-isoindole;2,3-dihydroIsoindole-5-carbonitrile;AKOS006286952;MB05811;AS-30290;DA-07547;SY240668;CS-0208603;EN300-269334;6-HYDROXY-2,4,5-TRIAMINOPYRIMIDINESULFATE;J-521547

Chemical Property of Isoindoline-5-carbonitrile

Chemical Property:

• Boiling Point: 273.2±40.0 °C(Predicted)
• PKA: 7.69±0.20(Predicted)
• PSA: 35.82000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 1.49028
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 144.068748264
• Heavy Atom Count: 11
• Complexity: 191

Purity/Quality:

99.0% ^*data from raw suppliers

Isoindoline-5-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(CN1)C=C(C=C2)C#N

Technology Process of Isoindoline-5-carbonitrile

There total 8 articles about Isoindoline-5-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: 99.9%

tert-butyl 5-cyanoisoindoline-2-carboxylate (263888-56-8) → 5-cyano-2,3-dihydro-1H-isoindole (263888-58-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 15 ℃; for 2h;

Reference yield:

5-methoxy-2,3-dihydro-1H-isoindole (127168-88-1) → 5-cyano-2,3-dihydro-1H-isoindole (263888-58-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / aq. HBr / 2 h / 100 °C

2: 40 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

3: 70 percent / Et₃N / CH₂Cl₂ / 6 h / -20 - 20 °C

4: 90 percent / Pd(PPh₃)4 / dimethylformamide / 4 h / 100 °C

5: 90 percent / TFA / CH₂Cl₂ / 0.5 h / 40 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen bromide; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00037-3

Reference yield:

5-hydroxyisoindoline (54544-67-1) → 5-cyano-2,3-dihydro-1H-isoindole (263888-58-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 40 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

2: 70 percent / Et₃N / CH₂Cl₂ / 6 h / -20 - 20 °C

3: 90 percent / Pd(PPh₃)4 / dimethylformamide / 4 h / 100 °C

4: 90 percent / TFA / CH₂Cl₂ / 0.5 h / 40 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00037-3

upstream raw materials:

tert-butyl 5-cyanoisoindoline-2-carboxylate

5-methoxy-2,3-dihydro-1H-isoindole

5-hydroxyisoindoline

tert-butyl 5-hydroxyisoindoline-2-carboxylate

Downstream raw materials:

{4-[2-(5-cyano-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester

2-[2-(4-amino-cyclohexyl)-ethyl]-2,3-dihydro-1H-isoindole-5-carbonitrile