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Cas Database

1428264-96-3

1428264-96-3

Identification

  • Product Name:C14H13NO

  • CAS Number: 1428264-96-3

  • EINECS:

  • Molecular Weight:211.263

  • Molecular Formula: C14H13NO

  • HS Code:

  • Mol File:1428264-96-3.mol

Synonyms:C14H13NO

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Relevant articles and documentsAll total 1 Articles be found

Modular synthesis of phenanthridine derivatives by oxidative cyclization of 2-isocyanobiphenyls with organoboron reagents

Tobisu, Mamoru,Koh, Keika,Furukawa, Takayuki,Chatani, Naoto

, p. 11363 - 11366 (2013/01/15)

Where HAS you been? A manganese-mediated annulation of 2-isocyanobiaryls with organoboronic acids is developed for the synthesis of a broad range of phenanthridine derivatives (see scheme). Mechanistic studies indicate that the reaction proceeds by the intramolecular homolytic aromatic substitution (HAS) of an imidoyl radical intermediate. Copyright

Process route upstream and downstream products

Process route

3-oxobutyraldehyde
625-34-3

3-oxobutyraldehyde

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

2-amino-5-methylbiphenyl

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

C14H13NO

Conditions
Conditions Yield
In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;
C<sub>14</sub>H<sub>13</sub>NO
1428264-96-3

C14H13NO

2‐methyl‐6‐phenylphenanthridine

2‐methyl‐6‐phenylphenanthridine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
2: manganese(III) acetylacetonate / toluene / 1 h / 80 °C / Inert atmosphere
With manganese(III) acetylacetonate; triethylamine; trichlorophosphate; In tetrahydrofuran; toluene;
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: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 °C
2: iron(II) chloride tetrahydrate; 1,10-Phenanthroline; tert.-butylhydroperoxide / water; ethyl acetate / 4 h / 80 °C
With tert.-butylhydroperoxide; 1,10-Phenanthroline; iron(II) chloride tetrahydrate; triethylamine; trichlorophosphate; In tetrahydrofuran; water; ethyl acetate;
Multi-step reaction with 2 steps
1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
2: potassium carbonate / dimethylsulfoxide-d6 / 24 h / 20 °C / Schlenk technique; Irradiation; Green chemistry
With potassium carbonate; triethylamine; trichlorophosphate; In tetrahydrofuran; dimethylsulfoxide-d6;
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;
C<sub>14</sub>H<sub>13</sub>NO
1428264-96-3

C14H13NO

(2‐methylphenanthridin‐6‐yl)diphenylphosphine oxide
1507941-20-9

(2‐methylphenanthridin‐6‐yl)diphenylphosphine oxide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: trichlorophosphate; triethylamine / tetrahydrofuran / 2 h / 0 °C / Schlenk technique; Inert atmosphere
2: triethylamine; Diphenyliodonium triflate / dichloromethane / 5 h / 40 °C / Schlenk technique; Inert atmosphere
With Diphenyliodonium triflate; triethylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane;
Multi-step reaction with 2 steps
1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
2: dipotassium peroxodisulfate; cesium fluoride / ethyl acetate / 12 h / 20 °C / Inert atmosphere; Irradiation; Schlenk technique; Green chemistry
With dipotassium peroxodisulfate; triethylamine; cesium fluoride; trichlorophosphate; In tetrahydrofuran; ethyl acetate;
Multi-step reaction with 2 steps
1: trichlorophosphate; triethylamine / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere
2: sodium hydrogencarbonate; tert.-butylhydroperoxide; (2r,4s,5r)-2,4,5,6-tetrakis(3,6-di-tert-butyl-9H-carbazol-9-yl)isophthalonitrile / acetonitrile / 12 h / 20 °C / Inert atmosphere; Irradiation
With tert.-butylhydroperoxide; (2r,4s,5r)-2,4,5,6-tetrakis(3,6-di-tert-butyl-9H-carbazol-9-yl)isophthalonitrile; sodium hydrogencarbonate; triethylamine; trichlorophosphate; In tetrahydrofuran; acetonitrile;
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;
C<sub>14</sub>H<sub>13</sub>NO
1428264-96-3

C14H13NO

6-(4-methoxyphenyl)-2-methylphenanthridine
1428265-01-3

6-(4-methoxyphenyl)-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;
C<sub>14</sub>H<sub>13</sub>NO
1428264-96-3

C14H13NO

6-(4-bromophenyl)-2-methylphenanthridine

6-(4-bromophenyl)-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;
C<sub>14</sub>H<sub>13</sub>NO
1428264-96-3

C14H13NO

(2-methylphenanthridin-6-yl)(phenyl)methanone
107209-64-3

(2-methylphenanthridin-6-yl)(phenyl)methanone

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine; trichlorophosphate / tetrahydrofuran / 2 h / 0 °C
2: iron(III) chloride; tert.-butylhydroperoxide / acetonitrile; decane / 24 h / 90 °C / Inert atmosphere
With tert.-butylhydroperoxide; iron(III) chloride; triethylamine; trichlorophosphate; In tetrahydrofuran; decane; acetonitrile;
C<sub>14</sub>H<sub>13</sub>NO
1428264-96-3

C14H13NO

2-methyl-6-(4-nitrophenyl)phenanthridine

2-methyl-6-(4-nitrophenyl)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;
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;
C<sub>14</sub>H<sub>13</sub>NO
1428264-96-3

C14H13NO

2-methyl-6-(m-tolyl)phenanthridine
1603837-64-4

2-methyl-6-(m-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;

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