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Cas Database

1603837-65-5

1603837-65-5

Identification

  • Product Name:6-(3-chlorophenyl)-2-methylphenanthridine

  • CAS Number: 1603837-65-5

  • EINECS:

  • Molecular Weight:303.791

  • Molecular Formula: C20H14ClN

  • HS Code:

  • Mol File:1603837-65-5.mol

Synonyms:6-(3-chlorophenyl)-2-methylphenanthridine

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Relevant articles and documentsAll total 2 Articles be found

Catalyst-free synthesis of phenanthridinesviaelectrochemical coupling of 2-isocyanobiphenyls and amines

Malviya, Bhanwar Kumar,Singh, Karandeep,Jaiswal, Pradeep K.,Karnatak, Manvika,Verma, Ved Prakash,Badsara, Satpal Singh,Sharma, Siddharth

, p. 6367 - 6378 (2021/04/16)

Catalyst free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction is reported in this study. The coupling reaction proceeds by the cathodic reduction ofin situformed diazonium ions, which are formed from anilines and an alkyl nitrite. The generated aryl radical diazonium ions coupled from isocyanides furnished the desired products in good yields. This cascade reaction was conducted in an undivided cell equipped with an RVC as the anode and Pt as the cathode usingnBu4NBF4as the electrolyte at room temperature. A series of detailed mechanistic studies have also been performed, including a radical clock experiment and cyclic voltammetry analysis.

Arylative cyclization of 2-isocyanobiphenyls with anilines: One-pot synthesis of 6-arylphenanthridines via competitive reaction pathways

Xia, Zhonghua,Huang, Jinbo,He, Yimiao,Zhao, Jiaji,Lei, Jian,Zhu, Qiang

, p. 2546 - 2549 (2014/05/20)

A transition-metal-free method for the synthesis of C6 phenanthridine derivatives by arylative cyclization of 2-isocyanobiphenyls with arylamines in one pot was developed. Mechanistic studies suggest that electrophilic aromatic substitution (SEAr) of a nitrilium intermediate and homolytic aromatic substitution (HAS) of an imidoyl radical intermediate are two competitive reaction pathways involved in the annulation step.

Process route upstream and downstream products

Process route

2-isocyano-5-methyl-1,1'-biphenyl
1428264-89-4

2-isocyano-5-methyl-1,1'-biphenyl

3-chloro-aniline
108-42-9

3-chloro-aniline

6-(3-chlorophenyl)-2-methylphenanthridine
1603837-65-5

6-(3-chlorophenyl)-2-methylphenanthridine

Conditions
Conditions Yield
With tert.-butylnitrite; sodium acetate; N,N`-dimethylethylenediamine; dibenzoyl peroxide; at 20 - 70 ℃; for 3.08333h; Schlenk technique; Inert atmosphere;
68%
2-isocyano-5-methyl-1,1'-biphenyl; 3-chloro-aniline; With tetrabutylammonium tetrafluoroborate; isopentyl nitrite; In acetonitrile; at 25 ℃; for 0.166667h;
In acetonitrile; at 25 ℃; for 16h; Inert atmosphere; Electrolysis;
66%
C<sub>14</sub>H<sub>13</sub>NO
1428264-96-3

C14H13NO

6-(3-chlorophenyl)-2-methylphenanthridine
1603837-65-5

6-(3-chlorophenyl)-2-methylphenanthridine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine; trichlorophosphate / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
2: dibenzoyl peroxide; sodium acetate; N,N`-dimethylethylenediamine; tert.-butylnitrite / 3.08 h / 20 - 70 °C / Schlenk technique; Inert atmosphere
With tert.-butylnitrite; sodium acetate; triethylamine; N,N`-dimethylethylenediamine; trichlorophosphate; dibenzoyl peroxide; In tetrahydrofuran;
Multi-step reaction with 2 steps
1.1: trichlorophosphate; triethylamine / tetrahydrofuran / 3 h / 0 °C
2.1: isopentyl nitrite; tetrabutylammonium tetrafluoroborate / acetonitrile / 0.17 h / 25 °C
2.2: 16 h / 25 °C / Inert atmosphere; Electrolysis
With tetrabutylammonium tetrafluoroborate; triethylamine; trichlorophosphate; isopentyl nitrite; In tetrahydrofuran; acetonitrile;
2-amino-5-methylbiphenyl
42308-28-1

2-amino-5-methylbiphenyl

6-(3-chlorophenyl)-2-methylphenanthridine
1603837-65-5

6-(3-chlorophenyl)-2-methylphenanthridine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 2 h / 0 - 20 °C
2: triethylamine; trichlorophosphate / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
3: dibenzoyl peroxide; sodium acetate; N,N`-dimethylethylenediamine; tert.-butylnitrite / 3.08 h / 20 - 70 °C / Schlenk technique; Inert atmosphere
With tert.-butylnitrite; sodium acetate; triethylamine; N,N`-dimethylethylenediamine; trichlorophosphate; dibenzoyl peroxide; In tetrahydrofuran;
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 2 h / 0 - 20 °C
2.1: trichlorophosphate; triethylamine / tetrahydrofuran / 3 h / 0 °C
3.1: isopentyl nitrite; tetrabutylammonium tetrafluoroborate / acetonitrile / 0.17 h / 25 °C
3.2: 16 h / 25 °C / Inert atmosphere; Electrolysis
With tetrabutylammonium tetrafluoroborate; triethylamine; trichlorophosphate; isopentyl nitrite; In tetrahydrofuran; acetonitrile;
phenylboronic acid
98-80-6

phenylboronic acid

6-(3-chlorophenyl)-2-methylphenanthridine
1603837-65-5

6-(3-chlorophenyl)-2-methylphenanthridine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: potassium carbonate / water; 1,2-dimethoxyethane / 0.5 h / 20 °C / Inert atmosphere
1.2: 20 - 80 °C / Inert atmosphere
2.1: tetrahydrofuran / 2 h / 0 - 20 °C
3.1: triethylamine; trichlorophosphate / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
4.1: dibenzoyl peroxide; sodium acetate; N,N`-dimethylethylenediamine; tert.-butylnitrite / 3.08 h / 20 - 70 °C / Schlenk technique; Inert atmosphere
With tert.-butylnitrite; sodium acetate; potassium carbonate; triethylamine; N,N`-dimethylethylenediamine; trichlorophosphate; dibenzoyl peroxide; In tetrahydrofuran; 1,2-dimethoxyethane; water;
2-bromo-p-toluidine
583-68-6

2-bromo-p-toluidine

6-(3-chlorophenyl)-2-methylphenanthridine
1603837-65-5

6-(3-chlorophenyl)-2-methylphenanthridine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: potassium carbonate / water; 1,2-dimethoxyethane / 0.5 h / 20 °C / Inert atmosphere
1.2: 20 - 80 °C / Inert atmosphere
2.1: tetrahydrofuran / 2 h / 0 - 20 °C
3.1: triethylamine; trichlorophosphate / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
4.1: dibenzoyl peroxide; sodium acetate; N,N`-dimethylethylenediamine; tert.-butylnitrite / 3.08 h / 20 - 70 °C / Schlenk technique; Inert atmosphere
With tert.-butylnitrite; sodium acetate; potassium carbonate; triethylamine; N,N`-dimethylethylenediamine; trichlorophosphate; dibenzoyl peroxide; In tetrahydrofuran; 1,2-dimethoxyethane; water;
2-isocyano-5-methyl-1,1'-biphenyl
1428264-89-4

2-isocyano-5-methyl-1,1'-biphenyl

3-chloro-aniline
108-42-9

3-chloro-aniline

6-(3-chlorophenyl)-2-methylphenanthridine
1603837-65-5

6-(3-chlorophenyl)-2-methylphenanthridine

Conditions
Conditions Yield
With tert.-butylnitrite; sodium acetate; N,N`-dimethylethylenediamine; dibenzoyl peroxide; at 20 - 70 ℃; for 3.08333h; Schlenk technique; Inert atmosphere;
68%
2-isocyano-5-methyl-1,1'-biphenyl; 3-chloro-aniline; With tetrabutylammonium tetrafluoroborate; isopentyl nitrite; In acetonitrile; at 25 ℃; for 0.166667h;
In acetonitrile; at 25 ℃; for 16h; Inert atmosphere; Electrolysis;
66%
C<sub>14</sub>H<sub>13</sub>NO
1428264-96-3

C14H13NO

6-(3-chlorophenyl)-2-methylphenanthridine
1603837-65-5

6-(3-chlorophenyl)-2-methylphenanthridine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine; trichlorophosphate / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
2: dibenzoyl peroxide; sodium acetate; N,N`-dimethylethylenediamine; tert.-butylnitrite / 3.08 h / 20 - 70 °C / Schlenk technique; Inert atmosphere
With tert.-butylnitrite; sodium acetate; triethylamine; N,N`-dimethylethylenediamine; trichlorophosphate; dibenzoyl peroxide; In tetrahydrofuran;
Multi-step reaction with 2 steps
1.1: trichlorophosphate; triethylamine / tetrahydrofuran / 3 h / 0 °C
2.1: isopentyl nitrite; tetrabutylammonium tetrafluoroborate / acetonitrile / 0.17 h / 25 °C
2.2: 16 h / 25 °C / Inert atmosphere; Electrolysis
With tetrabutylammonium tetrafluoroborate; triethylamine; trichlorophosphate; isopentyl nitrite; In tetrahydrofuran; acetonitrile;
2-amino-5-methylbiphenyl
42308-28-1

2-amino-5-methylbiphenyl

6-(3-chlorophenyl)-2-methylphenanthridine
1603837-65-5

6-(3-chlorophenyl)-2-methylphenanthridine

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: tetrahydrofuran / 2 h / 0 - 20 °C
2: triethylamine; trichlorophosphate / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
3: dibenzoyl peroxide; sodium acetate; N,N`-dimethylethylenediamine; tert.-butylnitrite / 3.08 h / 20 - 70 °C / Schlenk technique; Inert atmosphere
With tert.-butylnitrite; sodium acetate; triethylamine; N,N`-dimethylethylenediamine; trichlorophosphate; dibenzoyl peroxide; In tetrahydrofuran;
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 2 h / 0 - 20 °C
2.1: trichlorophosphate; triethylamine / tetrahydrofuran / 3 h / 0 °C
3.1: isopentyl nitrite; tetrabutylammonium tetrafluoroborate / acetonitrile / 0.17 h / 25 °C
3.2: 16 h / 25 °C / Inert atmosphere; Electrolysis
With tetrabutylammonium tetrafluoroborate; triethylamine; trichlorophosphate; isopentyl nitrite; In tetrahydrofuran; acetonitrile;
phenylboronic acid
98-80-6

phenylboronic acid

6-(3-chlorophenyl)-2-methylphenanthridine
1603837-65-5

6-(3-chlorophenyl)-2-methylphenanthridine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: potassium carbonate / water; 1,2-dimethoxyethane / 0.5 h / 20 °C / Inert atmosphere
1.2: 20 - 80 °C / Inert atmosphere
2.1: tetrahydrofuran / 2 h / 0 - 20 °C
3.1: triethylamine; trichlorophosphate / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
4.1: dibenzoyl peroxide; sodium acetate; N,N`-dimethylethylenediamine; tert.-butylnitrite / 3.08 h / 20 - 70 °C / Schlenk technique; Inert atmosphere
With tert.-butylnitrite; sodium acetate; potassium carbonate; triethylamine; N,N`-dimethylethylenediamine; trichlorophosphate; dibenzoyl peroxide; In tetrahydrofuran; 1,2-dimethoxyethane; water;
2-bromo-p-toluidine
583-68-6

2-bromo-p-toluidine

6-(3-chlorophenyl)-2-methylphenanthridine
1603837-65-5

6-(3-chlorophenyl)-2-methylphenanthridine

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1.1: potassium carbonate / water; 1,2-dimethoxyethane / 0.5 h / 20 °C / Inert atmosphere
1.2: 20 - 80 °C / Inert atmosphere
2.1: tetrahydrofuran / 2 h / 0 - 20 °C
3.1: triethylamine; trichlorophosphate / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
4.1: dibenzoyl peroxide; sodium acetate; N,N`-dimethylethylenediamine; tert.-butylnitrite / 3.08 h / 20 - 70 °C / Schlenk technique; Inert atmosphere
With tert.-butylnitrite; sodium acetate; potassium carbonate; triethylamine; N,N`-dimethylethylenediamine; trichlorophosphate; dibenzoyl peroxide; In tetrahydrofuran; 1,2-dimethoxyethane; water;

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