1,3,5-trichloro-2,4,6-triazine
phenylboronic acid
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With bis(tricyclohexylphosphine)nickel(II) dichloride; potassium carbonate In tetrahydrofuran at 70℃; for 12h; Reagent/catalyst; Solvent; Temperature; Friedel-Crafts Alkylation; Green chemistry; | 94.1% |
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 8h; Inert atmosphere; Reflux; | 71% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene for 8h; Inert atmosphere; Reflux; | 71% |
1,3,5-trichloro-2,4,6-triazine
benzene
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With aluminum (III) chloride In 5,5-dimethyl-1,3-cyclohexadiene at 70℃; for 4h; Time; Temperature; | 92% |
With hydrogenchloride; aluminum (III) chloride In water; chlorobenzene at 20℃; for 25h; Temperature; Reagent/catalyst; Cooling with ice; | 84% |
With aluminum (III) chloride In ethyl acetate; chlorobenzene at 18 - 22℃; for 4h; |
1,3,5-trichloro-2,4,6-triazine
phenylmagnesium bromide
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere; | 89% |
In tetrahydrofuran at 0 - 20℃; for 12h; | 80% |
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 13h; | 80.5% |
1,3,5-trichloro-2,4,6-triazine
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate In water; N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere; | 85.2% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; | 64% |
2,4-dichloro-6-phenyl-1,3,5-triazine
phenylboronic acid
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 10h; Inert atmosphere; | 75.4% |
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; toluene for 10h; Inert atmosphere; Reflux; | 75% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 10h; Inert atmosphere; | 67.3% |
Conditions | Yield |
---|---|
With N,N-diethylaniline; trichlorophosphate at 140℃; for 6h; Sealed tube; | 74% |
With thionyl chloride; phosphorus pentachloride; 1,2-dichloro-benzene at 140℃; |
bromobenzene
1,3,5-trichloro-2,4,6-triazine
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran for 4h; Inert atmosphere; Reflux; Stage #2: 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran for 5h; Inert atmosphere; | 73.5% |
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Stage #2: 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran for 7h; Reflux; Inert atmosphere; | 73.5% |
Stage #1: bromobenzene With magnesium In tetrahydrofuran at 40 - 50℃; Stage #2: 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran at -5 - 5℃; | 72.8% |
2,4-dichloro-6-phenyl-1,3,5-triazine
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water Reflux; | 66% |
2,4,6-trichloropyrimidine
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 90℃; | 65% |
2,4,6-trichloropyrimidine
phenylmagnesium bromide
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 50℃; for 10h; | 61% |
N-phenyl benzoyl amide
N′-cyanobenzamidine
A
2-chloro-4,6-diphenyl-1,3,5-triazine
B
(4,6-Diphenyl-1,3,5-triazin-2-yl)phenylamine
Conditions | Yield |
---|---|
With phosphorus pentachloride CH3CN, 1h, reflux; Yield given. Multistep reaction; | A 48% B n/a |
With phosphorus pentachloride CH3CN, 1h, reflux; Yield given. Multistep reaction; | A n/a B 25% |
1,3,5-trichloro-2,4,6-triazine
A
2,4-dichloro-6-phenyl-1,3,5-triazine
B
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With diethyl ether |
5-nitroso-2,4-diphenyl-imidazole
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With chloroform; phosphorus pentachloride |
N′-cyanobenzamidine
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
In toluene for 1h; Heating; Yield given; |
N′-cyanobenzamidine
N,N-dimethylbenzamide
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With trichlorophosphate 1.) 5 min, 100 deg C, 2.) CH3CN, 30 min, reflux; Yield given. Multistep reaction; |
chloroform
5-nitroso-2,4-diphenyl-imidazole
phosphorus pentachloride
2-chloro-4,6-diphenyl-1,3,5-triazine
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With trichlorophosphate |
bromobenzene
1,3,5-trichloro-2,4,6-triazine
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; water; toluene | |
With hydrogenchloride In tetrahydrofuran; water; chlorobenzene; toluene |
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / Reflux 2: tetrakis(triphenylphosphine) palladium(0); sodium hydroxide / tetrahydrofuran; water / Reflux View Scheme |
1,3,5-trichloro-2,4,6-triazine
phenylmagnesium chloride
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 15h; | 42.8 g |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 10 h / 80 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 10 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 10 h / 80 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 10 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / toluene / 10 h / Inert atmosphere; Reflux 2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / toluene; water / 10 h / Inert atmosphere; Reflux View Scheme |
Conditions | Yield |
---|---|
Stage #1: isocyanuric acid; benzene With 1-butyl-3-methylimidazolium Tetrafluoroborate In 1,2-dichloro-benzene at 5℃; for 2h; Stage #2: With hydrogenchloride In 1,2-dichloro-benzene at 5 - 15℃; for 12h; Reagent/catalyst; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pd catalyst / tetrahydrofuran / 5 h / 80 °C / Inert atmosphere 2: potassium phosphate; palladium diacetate / water; N,N-dimethyl-formamide / 10 h / 130 °C / Inert atmosphere View Scheme |
4-amino-3-nitrophenylboronic acid pinacol ester
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux; | 100% |
Conditions | Yield |
---|---|
Stage #1: 5,8-dihydro-indolo[2,3-C]carbazole With sodium hydride In N,N-dimethyl-formamide for 1h; Inert atmosphere; Stage #2: 2-chloro-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl acetamide Inert atmosphere; | 100% |
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In water Reflux; Inert atmosphere; |
3-bromo-9H-carbazole
2-chloro-4,6-diphenyl-1,3,5-triazine
3-bromo-9-(4,6-diphenyl-[1,3,5]triazin-2-yl)-9H-carbazole
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; | 98% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; Inert atmosphere; | 93.2% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; Inert atmosphere; | 90% |
2-chloro-4,6-diphenyl-1,3,5-triazine
4-Bromophenylboronic acid
2-(4-bromobenzenyl)-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; | 96% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene for 12h; Reflux; | 96.5% |
With tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride; potassium carbonate In ethanol; water; toluene at 78℃; for 10h; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 20h; Inert atmosphere; | 96% |
2-chloro-4,6-diphenyl-1,3,5-triazine
2,6-dichlorophenylboronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 12h; Reflux; Inert atmosphere; | 96% |
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With platinum(IV) oxide; water-d2 at 250℃; for 14h; | 96% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at -20℃; Suzuki Coupling; Reflux; | 95.3% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 10h; Inert atmosphere; Reflux; | 93% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 10h; Inert atmosphere; Reflux; | 93% |
2-chloro-4,6-diphenyl-1,3,5-triazine
anthracene-9-boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 12h; | 95% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 110℃; for 12h; Inert atmosphere; | 95.17% |
Stage #1: 2-chloro-4,6-diphenyl-1,3,5-triazine; anthracene-9-boronic acid With tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 0.5h; Inert atmosphere; Stage #2: With sodium carbonate In ethanol; toluene at 80℃; for 12h; Inert atmosphere; | 70% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 8h; Inert atmosphere; | 95% |
2-chloro-4,6-diphenyl-1,3,5-triazine
(3-bromophenyl)boronic acid
2-(3-bromo-phenyl)-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; | 95% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; | 95% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere; | 95% |
2-chloro-4,6-diphenyl-1,3,5-triazine
7-bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene
2-bromo-5- (4,6-diphenyl-1,3,5-triazin-2-yl)-7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole
Conditions | Yield |
---|---|
Stage #1: 7-bromo-12,12-dimethyl-10,12-dihydro-10-azaindeno[2,1-b]fluorene With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: 2-chloro-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide; mineral oil at 20℃; for 12h; | 95% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 15h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 3h; Reflux; | 95% |
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 100℃; for 16h; Suzuki Coupling; Inert atmosphere; | 95% |
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 100℃; for 16h; Inert atmosphere; |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 3h; | 95% |
2-chloro-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 120℃; for 3h; | 95% |
2-chloro-4,6-diphenyl-1,3,5-triazine
3,4,5-trifluorophenylboronic acid
Conditions | Yield |
---|---|
Stage #1: 2-chloro-4,6-diphenyl-1,3,5-triazine; 3,4,5-trifluorophenylboronic acid With potassium carbonate In tetrahydrofuran; water at 20℃; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 12h; Reflux; | 94% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 106℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; | 77% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; trifluoroacetic acid | |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 4.5h; Inert atmosphere; Heating; | 94% |
2-chloro-4,6-diphenyl-1,3,5-triazine
3-chloro-4-fluorophenylboronic acid
Conditions | Yield |
---|---|
With palladium diacetate; sodium carbonate; tris-(o-tolyl)phosphine In tetrahydrofuran; water for 2h; Inert atmosphere; Reflux; | 94% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene Reflux; | 82% |
2-chloro-4,6-diphenyl-1,3,5-triazine
3-bromo-9-(4,6-diphenyl-[1,3,5]triazin-2-yl)-9H-carbazole
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide | 94% |
2-chloro-4,6-diphenyl-1,3,5-triazine
3-(dibenzo[b,d]furan-4-yl)-9H-carbazole
3-(dibenzo[b,d]furan-4-yl)-9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazole
Conditions | Yield |
---|---|
Stage #1: 3-(dibenzo[b,d]furan-4-yl)-9H-carbazole With sodium hydride In N,N-dimethyl-formamide for 0.25h; Inert atmosphere; Stage #2: 2-chloro-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 93.5% |
Conditions | Yield |
---|---|
Stage #1: C28H17NO With sodium hydride In N,N-dimethyl-formamide for 0.25h; Inert atmosphere; Stage #2: 2-chloro-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide for 2h; | 93.5% |
2-chloro-4,6-diphenyl-1,3,5-triazine
sodium methylate
2-methoxy-4,6-diphenyl-1,3,5-triazine
Conditions | Yield |
---|---|
In methanol for 0.5h; Ambient temperature; | 93% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; | 93% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; | 93% |
1.Introduction of 2-Chloro-4,6-diphenyl-1,3,5-triazine
The 2-Chloro-4,6-diphenyl-1,3,5-triazine, with the CAS registry number 3842-55-5, is also known as 1,3,5-Triazine, 2-chloro-4,6-diphenyl-. This chemical's molecular formula is C15H10ClN3 and formula weight is 267.71. What's more, both its IUPAC name and systematic name are the same which is called 2-Chloro-4,6-diphenyl-1,3,5-triazine.
2.Physical properties about this chemical
(1)ACD/LogP: 4.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.36; (4)ACD/LogD (pH 7.4): 4.36; (5)ACD/BCF (pH 5.5): 1213.32; (6)ACD/BCF (pH 7.4): 1213.32; (7)ACD/KOC (pH 5.5): 5611.87; (8)ACD/KOC (pH 7.4): 5611.88; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 38.67 Å2; (13)Index of Refraction: 1.622; (14)Molar Refractivity: 74.6 cm3; (15)Molar Volume: 211.6 cm3; (16)Surface Tension: 53.4 dyne/cm; (17)Density: 1.265 g/cm3; (18)Flash Point: 279.2 °C; (19)Enthalpy of Vaporization: 72.19 kJ/mol; (20)Boiling Point: 485.1 °C at 760 mmHg; (21)Vapour Pressure: 4.3E-09 mmHg at 25°C.
3.Structure descriptors of 2-Chloro-4,6-diphenyl-1,3,5-triazine
(1)Canonical SMILES: C1=CC=C(C=C1)C2=NC(=NC(=N2)Cl)C3=CC=CC=C3
(2)InChI: InChI=1S/C15H10ClN3/c16-15-18-13(11-7-3-1-4-8-11)17-14(19-15)12-9-5-2-6-10-12/h1-10H
(3)InChIKey: DDGPPAMADXTGTN-UHFFFAOYSA-N
4. Preparation of 2-Chloro-4,6-diphenyl-1,3,5-triazine
2-Chloro-4,6-diphenyl-1,3,5-triazine can be prepared by N-Phenyl-benzamide and N-Cyano-benzamidine. This reaction will need reagent PCl5. The reaction time is 1 hour. The yield is about 48%.
5.Uses of 2-Chloro-4,6-diphenyl-1,3,5-triazine
2-Chloro-4,6-diphenyl-1,3,5-triazine can be used to produce 2-Ethoxy-4,6-diphenyl-[1,3,5]triazine at the ambient temperature. This reaction will need reagent sodium methanolate and solvent ethanol with reaction time of 7 days. The yield is about 36.1%.
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