Tert-butyl 5-cyanoisoindoline-2-carboxylate

Base Information

• Chemical Name: Tert-butyl 5-cyanoisoindoline-2-carboxylate
• CAS No.: 263888-56-8
• Molecular Formula: C14H16 N2 O2
• Molecular Weight: 244.29
• DSSTox Substance ID: DTXSID80595323
• Wikidata: Q82490318
• Mol file: 263888-56-8.mol

Synonyms:TERT-BUTYL 5-CYANOISOINDOLINE-2-CARBOXYLATE;263888-56-8;tert-butyl 5-cyano-1,3-dihydroisoindole-2-carboxylate;2H-Isoindole-2-carboxylic acid, 5-cyano-1,3-dihydro-, 1,1-dimethylethyl ester;TERT-BUTYL5-CYANOISOINDOLINE-2-CARBOXYLATE;SCHEMBL566550;DTXSID80595323;IXXSRJYZPJRWPB-UHFFFAOYSA-N;AB6612;MFCD08234856;N-t-Butoxycarbonyl-5-cyanoisoindoline;AKOS022681478;MB05806;AS-44787;DA-42988;CS-0208583;EN300-306410;2-(tert-butyloxycarbonyl)-5-cyano-2,3-dihydro-1H-isoindol;tert-Butyl 5-cyano-1,3-dihydro-2H-isoindole-2-carboxylate;2-(tert-butyloxycarbonyl)-5-cyano-2,3-dihydro-1H-isoindole;5-Cyano-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester;TERT-BUTYL 5-CYANO-2,3-DIHYDRO-1H-ISOINDOLE-2-CARBOXYLATE

Chemical Property of Tert-butyl 5-cyanoisoindoline-2-carboxylate

Chemical Property:

• Boiling Point: 367.9±42.0 °C(Predicted)
• PKA: -1.75±0.20(Predicted)
• PSA: 53.33000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 2.74688
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 244.121177757
• Heavy Atom Count: 18
• Complexity: 377

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl5-cyanoisoindoline-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC2=C(C1)C=C(C=C2)C#N

Technology Process of Tert-butyl 5-cyanoisoindoline-2-carboxylate

There total 15 articles about Tert-butyl 5-cyanoisoindoline-2-carboxylate 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: 97.6%

5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (201940-08-1) + zinc(II) cyanide (557-21-1) → tert-butyl 5-cyanoisoindoline-2-carboxylate (263888-56-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 80 ℃; for 3h;

Reference yield: 90.0%

dicyanozinc (557-21-1) + 5-trifluoromethanesulfonyloxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (263888-57-9) → tert-butyl 5-cyanoisoindoline-2-carboxylate (263888-56-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 100 ℃; for 4h;

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

Reference yield: 85.0%

→ tert-butyl 5-cyanoisoindoline-2-carboxylate (263888-56-8)

Guidance literature:

upstream raw materials:

dicyanozinc

5-trifluoromethanesulfonyloxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

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

Downstream raw materials:

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

5-formyl-1,2-dihydro-isoindole-2-carboxylic acid tertiary butyl ester

{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