1,2,3,4-Tetrahydroisoquinoline-6-carbonitrile

Base Information

• Chemical Name: 1,2,3,4-Tetrahydroisoquinoline-6-carbonitrile
• CAS No.: 166398-34-1
• Molecular Formula: C10H10N2
• Molecular Weight: 158.203
• Hs Code.: 2933499090
• European Community (EC) Number: 830-837-4
• DSSTox Substance ID: DTXSID10437121
• Nikkaji Number: J678.941B
• Wikidata: Q72505868
• ChEMBL ID: CHEMBL4076796
• Mol file: 166398-34-1.mol

Synonyms:1,2,3,4-tetrahydroisoquinoline-6-carbonitrile;166398-34-1;6-ISOQUINOLINECARBONITRILE, 1,2,3,4-TETRAHYDRO-;CHEMBL4076796;SCHEMBL1638541;DTXSID10437121;RKWNQODBLXZUES-UHFFFAOYSA-N;BDBM50267215;AKOS006276440;AB16298;AM803297;6-cyano-1,2,3,4-tetrahydro-isoquinoline;A3687;CS-0447795;FT-0648423;1,2,3,4-tetrahydro-isoquinolin-6-carbonitrile;EN300-268714;J-503766;1,2,3,4-TETRAHYDRO-6-ISOQUINOLINECARBONITRILE;Z1198163344

Chemical Property of 1,2,3,4-Tetrahydroisoquinoline-6-carbonitrile

Chemical Property:

• Vapor Pressure: 0.000103mmHg at 25°C
• Boiling Point: 301.519 °C at 760 mmHg
• PKA: 8.58±0.20(Predicted)
• Flash Point: 136.154 °C
• PSA: 35.82000
• Density: 1.148 g/cm³
• LogP: 1.53278
• Storage Temp.: 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 158.084398327
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,2,3,4-Tetrahydroisoquinoline-6-carbonitrile 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CNCC2=C1C=C(C=C2)C#N

Technology Process of 1,2,3,4-Tetrahydroisoquinoline-6-carbonitrile

There total 6 articles about 1,2,3,4-Tetrahydroisoquinoline-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: 100.0%

tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate (166398-33-0) → 1,2,3,4-tetrahydroisoquinoline-6-carbonitrile (166398-34-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/j.ejmech.2021.113841

Reference yield: 77.0%

zinc(II) cyanide (557-21-1) + 6-bromo-1,2,3,4-tetrahydroisoquinoline (226942-29-6) → 1,2,3,4-tetrahydroisoquinoline-6-carbonitrile (166398-34-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 130 ℃; for 1h; Microwave irradiation;

DOI:10.1021/ml2000214

Reference yield:

6-cyano-1,2,3,4-tetrahydroisoquinoline hydrochloride → 1,2,3,4-tetrahydroisoquinoline-6-carbonitrile (166398-34-1)

Guidance literature:

With sodium hydroxide; In water;

upstream raw materials:

zinc(II) cyanide

6-bromo-1,2,3,4-tetrahydroisoquinoline

6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline

tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate

Downstream raw materials:

trans-2-(2-(1-4-(N-tert-butyloxycarbonyl)amino)cyclohexyl)ethyl-6-cyano-1,2,3,4-tetrahydroisoquinoline

tert-butyl 6-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate

tert-butyl 6-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

2-isopropoxy-5-(3-(1,2,3,4-tetrahydroisoquinolin-6-yl)-1,2,4-oxadiazol-5-yl)benzonitrile trifluoroacetate

Refernces

• 1、 Demont, Emmanuel H.,Andrews, Benjamin I.,Bit, Rino A.,Campbell, Colin A.,Cooke, Jason W. B.,Deeks, Nigel,Desai, Sapna,Dowell, Simon J.,Gaskin, Pam,Gray, James R. J.,Haynes, Andrea,Holmes, Duncan S.,Kumar, Umesh,Morse, Mary A.,Osborne, Greg J.,Panchal, Terry,Patel, Bela,Perboni, Alcide,Taylor, Simon,Watson, Robert,Witherington, Jason,Willis, Robert. "Discovery of a selective S1P1 receptor agonist efficacious at low oral dose and devoid of effects on heart rate". supporting information; experimental part. p. 444 - 449. Retrieved 2011/08/08.
• 2、 -. "S1P1 AGONISTS COMPRISING A BICYCLIC N-CONTAINING RING". Page/Page column 170. . Retrieved 2010/12/31.