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Cas Database

1603837-51-9

1603837-51-9

Identification

  • Product Name:2-methyl-6-(p-tolyl)phenanthridine

  • CAS Number: 1603837-51-9

  • EINECS:

  • Molecular Weight:283.373

  • Molecular Formula: C21H17N

  • HS Code:

  • Mol File:1603837-51-9.mol

Synonyms:2-methyl-6-(p-tolyl)phenanthridine

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Relevant articles and documentsAll total 2 Articles be found

Synthesis of phenanthridines by I2-mediated sp3C-H amination

Chang, Junbiao,Fang, Benyao,Hou, Jiao,Tian, Jinyue,Yu, Wenquan

, p. 3312 - 3323 (2020/05/14)

An I2-mediated synthesis of phenanthridinesviaintramolecular sp3C-H amination of readily accessible aniline precursors is reported. The present synthetic process is straightforward and applicable to a broad variety of unprotected ani

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

2-methyl-6-(p-tolyl)phenanthridine
1603837-51-9

2-methyl-6-(p-tolyl)phenanthridine

Conditions
Conditions Yield
With tert.-butylnitrite; sodium acetate; N,N`-dimethylethylenediamine; dibenzoyl peroxide; at 20 - 70 ℃; for 3.08333h; Reagent/catalyst; Temperature; Solvent; Schlenk technique; Inert atmosphere;
89%
5-methyl-2'-(4-methylbenzyl)[1,1'-biphenyl]-2-amine

5-methyl-2'-(4-methylbenzyl)[1,1'-biphenyl]-2-amine

2-methyl-6-(p-tolyl)phenanthridine
1603837-51-9

2-methyl-6-(p-tolyl)phenanthridine

Conditions
Conditions Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; iodine; caesium carbonate; at 80 ℃; for 2h;
85%
phenylboronic acid
98-80-6

phenylboronic acid

2-methyl-6-(p-tolyl)phenanthridine
1603837-51-9

2-methyl-6-(p-tolyl)phenanthridine

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;
C<sub>14</sub>H<sub>13</sub>NO
1428264-96-3

C14H13NO

2-methyl-6-(p-tolyl)phenanthridine
1603837-51-9

2-methyl-6-(p-tolyl)phenanthridine

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;
2-amino-5-methylbiphenyl
42308-28-1

2-amino-5-methylbiphenyl

2-methyl-6-(p-tolyl)phenanthridine
1603837-51-9

2-methyl-6-(p-tolyl)phenanthridine

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;
2-bromo-p-toluidine
583-68-6

2-bromo-p-toluidine

2-methyl-6-(p-tolyl)phenanthridine
1603837-51-9

2-methyl-6-(p-tolyl)phenanthridine

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-(4-methylbenzyl)phenyl)boronic acid

(2-(4-methylbenzyl)phenyl)boronic acid

2-methyl-6-(p-tolyl)phenanthridine
1603837-51-9

2-methyl-6-(p-tolyl)phenanthridine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 12 h / Inert atmosphere; Reflux
2: iodine; caesium carbonate; N,N,N,N,N,N-hexamethylphosphoric triamide / 2 h / 80 °C
With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrakis(triphenylphosphine) palladium(0); iodine; potassium carbonate; caesium carbonate; In ethanol; water; toluene;
2-isocyano-5-methyl-1,1'-biphenyl
1428264-89-4

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

2-methyl-6-(p-tolyl)phenanthridine
1603837-51-9

2-methyl-6-(p-tolyl)phenanthridine

Conditions
Conditions Yield
With tert.-butylnitrite; sodium acetate; N,N`-dimethylethylenediamine; dibenzoyl peroxide; at 20 - 70 ℃; for 3.08333h; Reagent/catalyst; Temperature; Solvent; Schlenk technique; Inert atmosphere;
89%
5-methyl-2'-(4-methylbenzyl)[1,1'-biphenyl]-2-amine

5-methyl-2'-(4-methylbenzyl)[1,1'-biphenyl]-2-amine

2-methyl-6-(p-tolyl)phenanthridine
1603837-51-9

2-methyl-6-(p-tolyl)phenanthridine

Conditions
Conditions Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; iodine; caesium carbonate; at 80 ℃; for 2h;
85%
phenylboronic acid
98-80-6

phenylboronic acid

2-methyl-6-(p-tolyl)phenanthridine
1603837-51-9

2-methyl-6-(p-tolyl)phenanthridine

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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