2-(3,4-dihydro-2H-quinolin-1-yl)acetonitrile

Base Information

• Chemical Name: 2-(3,4-dihydro-2H-quinolin-1-yl)acetonitrile
• CAS No.: 66487-31-8
• Molecular Formula: C11H12N2
• Molecular Weight: 172.22600
• European Community (EC) Number: 660-042-6
• Nikkaji Number: J3.559.538D
• Mol file: 66487-31-8.mol

Synonyms:66487-31-8;2-(1,2,3,4-tetrahydroquinolin-1-yl)acetonitrile;2-(3,4-dihydro-2H-quinolin-1-yl)acetonitrile;1-CyanoMethyl-1,2,3,4-tetrahydro-quinoline;2-(3,4-dihydroquinolin-1(2H)-yl)acetonitrile;SCHEMBL11521841;TUCDZHYOISPGQH-UHFFFAOYSA-N;AKOS000167186;AS-65667;3,4-dihydro-1(2H)-quinolinylacetonitrile;N-cyanomethyl-1,2,3,4-tetrahydroquinoline;1,2,3,4-Tetrahydroquinoline-1-acetonitrile;CS-0256694;J3.559.538D;D96075;EN300-651101;Z169225618

Chemical Property of 2-(3,4-dihydro-2H-quinolin-1-yl)acetonitrile

Chemical Property:

• Boiling Point: 337.9±25.0 °C(Predicted)
• PKA: 2.65±0.20(Predicted)
• PSA: 27.03000
• Density: 1.088±0.06 g/cm3(Predicted)
• LogP: 2.02778
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 172.100048391
• Heavy Atom Count: 13
• Complexity: 215

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=CC=CC=C2N(C1)CC#N

Technology Process of 2-(3,4-dihydro-2H-quinolin-1-yl)acetonitrile

There total 9 articles about 2-(3,4-dihydro-2H-quinolin-1-yl)acetonitrile 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: 92.0%

1,2,3,4-tetrahydroisoquinoline (635-46-1) + cyanomethyl bromide (590-17-0) → 2-(3,4-dihydroquinolin-1(2H)-yl)acetonitrile (66487-31-8)

Guidance literature:

1,2,3,4-tetrahydroisoquinoline; cyanomethyl bromide; With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 4h;

With sodium hydroxide; In dichloromethane; water;

Reference yield: 84.0%

→ 2-(3,4-dihydroquinolin-1(2H)-yl)acetonitrile (66487-31-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 4h; Reflux;

Reference yield: 74.0%

1,2,3,4-tetrahydroisoquinoline (635-46-1) + trimethylsilyl cyanide (7677-24-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-(3,4-dihydroquinolin-1(2H)-yl)acetonitrile (66487-31-8)

Guidance literature:

With copper diacetate; N-fluorobis(benzenesulfon)imide; 4,4'-di-tert-butyl-2,2'-bipyridine; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c8cc00485d

upstream raw materials:

formaldehyd

decahydroquinoline

1,2,3,4-tetrahydroisoquinoline

cyanomethyl bromide

Downstream raw materials:

N-(β-aminoethyl)tetrahydroquinoline

Refernces

• 1、 Yuan, Zaifeng,Li, Na,Zhu, Chunyu,Xia, Chengfeng. "Copper-catalyzed synthesis of α-amino nitriles through methyl transfer from DMF to aromatic amines". supporting information. p. 2854 - 2857. Retrieved 2018/03/23.
• 2、 -. "CURE ACCELERATORS FOR ANAEROBIC CURABLE COMPOSITIONS". Paragraph 0086; 0087. . Retrieved 2017/07/14.