3,4-Dihydroisoquinoline

Base Information

• Chemical Name: 3,4-Dihydroisoquinoline
• CAS No.: 3230-65-7
• Molecular Formula: C9H9N
• Molecular Weight: 131.177
• European Community (EC) Number: 221-769-0
• NSC Number: 3007
• UNII: 2K2ZCG3PSZ
• DSSTox Substance ID: DTXSID20186037
• Nikkaji Number: J262.336F
• Wikidata: Q72465363
• Mol file: 3230-65-7.mol

Synonyms:3,4-dihydroisoquinoline;G 1616

Chemical Property of 3,4-Dihydroisoquinoline

Chemical Property:

• Vapor Pressure: 0.0548mmHg at 25°C
• Melting Point: 251-254℃
• Refractive Index: 1.6041 (589.3 nm 30℃)
• Boiling Point: 241.8 °C at 760 mmHg
• PKA: 5.80±0.20(Predicted)
• Flash Point: 91.6 °C
• PSA: 12.36000
• Density: 1.05 g/cm³
• LogP: 1.09720
• Storage Temp.: 2-8°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 131.073499291
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

99% ^*data from raw suppliers

3,4-Dihydroisoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 22-24-36/38
• Safety Statements: 26-36/37-45

MSDS Files:

Useful:

• Canonical SMILES: C1CN=CC2=CC=CC=C21
• Uses: 3,4-Dihydroisoquinoline is derived from 1,2,3,4-Tetrahydroisoquinoline (T293820), which is used as a reagent in the preparation of 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides as antiproliferative tubulin inhibitors. 3,4-Dihydroisoquinoline can be used as a reactant to synthesize: 5,6-Dihydro-8H-isoquino[1,2-b]quinazolin-8-one by decarboxylative cyclization reaction with isatoic anhydride using tetrabutylammonium iodide (TBAI). 1-naphtholyl tetrahydroisoquinoline by aza-Friedel-Crafts reaction with various naphthols. 3,4-dihydroisoquinoline pseudo bases, which are employed as starting materials for the preperation of 3-benzazepine derivatives.

Technology Process of 3,4-Dihydroisoquinoline

There total 86 articles about 3,4-Dihydroisoquinoline 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: 99.0%

N-(2-phenylethyl)formamide (23069-99-0) → 3,4-dihydroisoquinoline (3230-65-7)

Guidance literature:

With PPA; at 200 - 220 ℃; for 1h;

DOI:10.1002/jhet.5570420426

Reference yield: 91.0%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + 3-Trifluoromethylbenzaldehyde (454-89-7) → 3,4-dihydroisoquinoline (3230-65-7) + (3,4-dihydroisoquinolin-2(1H)-yl)(3-(trifluoromethyl)phenyl)methanone

Guidance literature:

With safranin O; In tetrahydrofuran; at 20 ℃; for 20h; Sealed tube; Irradiation; Green chemistry;

DOI:10.1021/ol5029354

Reference yield: 91.0%

decahydroisoquinoline (2744-08-3,2744-09-4,6329-61-9) → 3,4-dihydroisoquinoline (3230-65-7)

Guidance literature:

decahydroisoquinoline; With N-Bromosuccinimide; In dichloromethane; at 20 ℃; for 1h;

With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 3h;

DOI:10.1021/jo502842s

upstream raw materials:

1,2,3,4-tetrahydroisoquinoline

N-(2-phenylethyl)formamide

2'-(2-chloroethyl)benzaldehyde

2-(2-bromoethyl)benzaldehyde

Downstream raw materials:

1-(3,4-dimethoxyphenyl)-2-ethoxycarbonyltetrahydroisoquinoline

1-(α-hydroxy-2-naphthyl)-1,2,3,4-tetrahydroisoqinoline

1-(β-hydroxy-1-naphthyl)-1,2,3,4-tetrahydroisoqinoline

7-amino-3,4-dihydroisoquinoline

Refernces

• 1、 Shimizu, Masao,Orita, Hideo,Hayakawa, Takashi,Suzuki, Kunio,Takehira, Katsuomi. "OXIDATION OF 1,2,3,4-TETRAHYDROISOQUINOLINES TO 3,4-DIHYDROISOQUINOLINES WITH MOLECULAR OXYGEN CATALYZED BY COPPER(II) CHLORIDE". . p. 773 - 780. Retrieved 1995.
• 2、 Tiwari, Dharmendra Kumar,Maurya, Ram Awatar,Nanubolu, Jagadeesh Babu. "Visible-Light/Photoredox-Mediated sp3 C-H Functionalization and Coupling of Secondary Amines with Vinyl Azides in Flow Microreactors". . p. 526 - 530. Retrieved 2016.
• 3、 Xiang, Ming,Xu, Zhihua,Wang, Jinghao,Yang, Xiaoqiu,Yan, Zhaoxiong. "Accelerating H2 Evolution by Anodic Semi-dehydrogenation of Tetrahydroisoquinolines in Water over Co3O4 Nanoribbon Arrays Decorated Nickel Foam". . p. 7502 - 7506. Retrieved 2021.
• 4、 Cui, Fu-Jun,Guo, Fu-Hu,Liu, Jing-Jiang,Liu, Xiao-Yu,Quan, Zheng-Jun,Ullah, Arif,Wang, Xi-Cun,Zhu, Ji-Hua. "A biomass-derived N-doped porous carbon catalyst for the aerobic dehydrogenation of nitrogen heterocycles". supporting information. p. 1791 - 1799. Retrieved 2022/01/31.
• 5、 Liu, Shuyang,Tian, Miao,Bu, Xiubin,Tian, Hua,Yang, Xiaobo. "Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations". . p. 7738 - 7744. Retrieved 2021/05/07.