Home Cart 0 Sign in  

[ CAS No. 1229012-68-3 ]

{[proInfo.proName]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 1229012-68-3
Chemical Structure| 1229012-68-3
Structure of 1229012-68-3 *Storage: {[proInfo.prStorage]}

Quality Control of [ 1229012-68-3 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 1229012-68-3 ]

SDS

Product Details of [ 1229012-68-3 ]

CAS No. :1229012-68-3MDL No. :MFCD26398601
Formula :C24H14Cl2N2Boiling Point :-
Linear Structure Formula :-InChI Key :N/A
M.W :401.29Pubchem ID :46240522
Synonyms :

Computed Properties of [ 1229012-68-3 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 1229012-68-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305 P351 P338UN#:N/A
Hazard Statements:H302Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1229012-68-3 ]

  • Downstream synthetic route of [ 1229012-68-3 ]

[ 1229012-68-3 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 1229012-68-3 ]
  • [ 197958-29-5 ]
  • C34H22N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12.0h;Inert atmosphere; Reflux; Under the protection of nitrogen, the intermediates S25 (1mmol) and S3 (2.2mmol) were dissolved in 30mL toluene, tetrakistriphenylphosphine palladium Pd (PPh3) 4 (0.1mmol) was added as a catalyst, and 4mL aqueous potassium carbonate solution (2mol / L), reflux for 12h; after the reaction is completed, extract three times with saturated brine and ethyl acetate, and combine the organic phases. All solvents were distilled off under reduced pressure, and the crude product was collected. The crude product was purified through a silica gel chromatography column, using a mixed solvent with a volume ratio of n-hexane to chloroform of 5: 1 as an eluent, and finally purified to obtain a solid comparative compound 3 (0.83 mmol, yield 83%).
  • 2
  • [ 1229012-68-3 ]
  • [ 1143576-84-4 ]
  • 2-chloro-4,7-diphenyl-9-(4-(10-phenylanthracen 9-yl)phenyl)-1,10-phenanthroline [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.8% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 100℃; for 12.0h;Inert atmosphere; Synthesis of 2-chloro-4,7-diphenyl-9-(4-(10-phenylanthracen 9-yl)phenyl)-1,10-phenanthroline A mixture of 6.8 g (16.9 mmol) of [1229012-68-3]2,9-dichloro-4,7-diphenyl-1,10-phenanthroline, 7.7 g (16.9 mmol) of 4,4,5,5-tetramethyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1,3,2-dioxaborolane, 196 mg (0.17 mmol) of Pd(PPh3)4, 17 ml of 2M Na2CO3, 50 ml of EtOH and 150 ml toluene was degassed and placed under nitrogen, and then heated at 100 C. for 12 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica to give product (6 g, 8.6 mmol, 50.8%) as a yellow solid.
  • 3
  • [ 1229012-66-1 ]
  • [ 1229012-68-3 ]
YieldReaction ConditionsOperation in experiment
With phosphorus pentachloride; trichlorophosphate; for 8.0h;Inert atmosphere; Reflux; c) Combined portions of diketone from step (b) above totaling 5.5 g (13.6 mM) were suspended in 39 mL POCl3 and 5.4 g PCl5 was added. This was degassed and refluxed under nitrogen for 8 hrs. The excess POCl3 was removed by evaporation. Ice was added to decompose the remaining chlorides and the mixture was neutralized with ammonia solution. The brown precipitate was collected and dried under vacuum while the mother liquor was extracted with methylene chloride. All brown material was combined, evaporated to a brown gum and methanol added. After shaking and stirring a pale yellow solid was isolated which recrystallized as off-white needles from CHCl3 and methanol (1:10). Analysis by NMR indicated the dichlorobathophenanthroline structure below.
  • 4
  • 2Br(1-)*C27H22N2(2+) [ No CAS ]
  • [ 1229012-68-3 ]
  • 5
  • [ 1229012-68-3 ]
  • [ 928050-08-2 ]
  • [ 1233221-52-7 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; at 80 - 100℃;Inert atmosphere; Example 7; This example illustrates the preparation of phenanthroline derivative Compound 12, using Suzuki coupling of [1229012-68-3]2,9-dichloro-4,7-diphenyl-1,10-phenanthroline from Example 1 with the boronic ester shown below. Take 1.0 g of dichloro-phen (2.5 mM) in glove box and add 3.12 g (6 mM) boronic ester. Add 0.15 g Pd2 DBA3 (0.15 mM), 0.1 g tricyclohexylphosphine (0.35 mM) and 2.0 g potassium phosphate (9 mM) and dissolve all into 30 mL dioxane and 15 mL water. Mix and heat in glove box in mantle at 100 C for 1 hr then warm gently (minimum rheostat setting) under nitrogen overnight. Solution immediately is dark purple but on reaching 80 C it is a tan brown slurry which slowly becomes clear brown with a dense ppt. As the solution refluxes (air condensor) a brown gummy material forms. Cool and work up by removing from glove box and add water. Extract into DCM and dry over magnesium sulfate. Chromatograph on a plug of silica/florisil eluting with DCM then DCM/methanol 2:1. Collect a pale yellow solution which was evaporated and upon addition of methanol ppts a white/pale yellow solid. The structure was confirmed by NMR analysis to be Compound 12:
  • 6
  • [ 1229012-68-3 ]
  • [ 1016653-37-4 ]
  • [ 1233221-51-6 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; at 80 - 100℃;Inert atmosphere; Example 6; This example illustrates the preparation of phenanthroline derivative Compound 11, using Suzuki coupling of [1229012-68-3]2,9-dichloro-4,7-diphenyl-1,10-phenanthroline from Example 1 with the boronic ester shown below. Take 1.0 g of dichloro-phen (2.5 mM) in glove box and add 2.6 g (5.5 mM) boronic ester. Add 0.15 g Pd2 DBA3 (0.15 mM), 0.1 g tricyclohexylphosphine (0.35 mM) and 3.75 g potassium phosphate (17 mM) and dissolve all into 30 mL dioxane and 15 mL water. Mix and heat in glove box in mantle at 100 C for 1 hr then warm gently (minimum rheostat setting) under nitrogen overnight. Solution immediately is dark purple but on reaching 80 C it is a tan brown slurry which slowly becomes clear brown. As the solution cools a flocculent ppt forms. Cool and work up by removing from glove box and adding more water. Separate the aqueous and organic layers and wash aq layer with DCM. Combine all organic layers, dry on magnesium sulfate and filter through a silica plug. Collect the orange solution which was evaporated to low volume and methanol added to ppt a pale orange solid. Dissolve in hot toluene/DCM and run through a silica/florisil/B-alumina stacked column eluting with DCM/Toluene as a pale yellow solution. Material is strongly colored on the chromatographic medium. -especially florisil. Evaporate to low volume and add methanol to ppt a yellow solid. isolate 2.55 g material. The structure was confirmed by NMR analysis to be Compound 11:
  • 7
  • [ 1092390-02-7 ]
  • [ 1229012-68-3 ]
  • [ 1233221-53-8 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; at 80 - 110℃;Inert atmosphere; Example 8; This example illustrates the preparation of phenanthroline derivative Compound 13, using Suzuki coupling of [1229012-68-3]2,9-dichloro-4,7-diphenyl-1,10-phenanthroline from Example 1 with the boronic ester shown below. Take 2.0 g of dichloro-phen (5 mM) in glove box and add 3.4 g (11 mM) boronic acid. Add 0.15 g Pd2 DBA3 (0.15 mM), 0.1 g tricyclohexylphosphine (0.35 mM) and 3.75 g potassium phosphate (17 mM) and dissolve all into 30 mL dioxane and 15 mL water. Mix and heat in glove box in mantle at 110 C for 1 hr then warm gently (minimum rheostat setting) under nitrogen overnight. Solution immediately is dark purple but on reaching 80 C it is a tan brown slurry which slowly becomes clear brown with a dense ppt. As the solution refluxes (air condensor) a white fibrous ppt forms. Cool and work up by removing from glove box and filter off white fibers from the dioxane after adding more water. Dissolve into chloroform and then evaporate and ppt in toluene by adding methanol as off white fine needles. Collect by filtration and wash well with methanol to isolate 2.25 g material. The structure was confirmed by NMR analysis as Compound 13:
  • 8
  • [ 1229012-68-3 ]
  • [ 201802-67-7 ]
  • [ 1123553-91-2 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; at 80 - 100℃;Inert atmosphere; Example 3; This example illustrates the preparation of phenanthroline derivative Compound 4, using Suzuki coupling of [1229012-68-3]2,9-dichloro-4,7-diphenyl-1,10-phenanthroline from Example 1 with 4-triphenylaminoboronic acid.; To 2.0 g of dichlorobathophenanthroline (5 mM) from Example 1 was added 3.0 g (11 mM) boronic acid. To this was added 0.15 g Pd2 DBA3 (0.15 mM), 0.1 g tricyclohexylphosphine (0.35 mM) and 3.75 g potassium phosphate (17 mM), and all were dissolved into 30 mL dioxane and 15 mL water. This was mixed and heated in a glove box at 100 C. for 1 hr, then warmed gently (minimum rheostat setting) under nitrogen overnight. On reaching about 80 C. the mixture was a tan brown slurry which slowly became clear brown with a dense precipitate. As the solution refluxed (air condensor) a white powdery precipitate formed. The mixture was cooled and removed from the glove box. The dioxane was removed by evaporation and additional water added. A light brown gummy solid was isolated by filtration and washed with water. The solid dissolved well in toluene and dichloromethane. The product was Compound 4.
  • 9
  • [ 1662-01-7 ]
  • [ 1229012-68-3 ]
  • 10
  • [ 1229012-68-3 ]
  • [ 4688-76-0 ]
  • [ 625121-77-9 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; at 80 - 100℃;Inert atmosphere; Example 4; This example illustrates the preparation of phenanthroline derivative Compound 9, using Suzuki coupling of [1229012-68-3]2,9-dichloro-4,7-diphenyl-1,10-phenanthroline from Example 1 with the boronic ester shown below. Take 2.0 g of dichloro-phen (5 mM) in glove box and add 2.0 g (11 mM) boronic ester (Aldrich). Add 0.15 g Pd2 DBA3 (0.15 mM), 0.1 g tricylohexylphosphine (0.35 mM) and 3.75 g potassium phosphate (17 mM) and dissolve all into 30 mL dioxane and 15 mL water. Mix and heat in glove box in mantle at 100 C for 1 hr then warm gently (minimum rheostat setting) under nitrogen overnight. Solution immediately is dark purple but on reaching 80 C it is a tan brown slurry which slowly becomes clear brown. As the solution cools a flocculent ppt forms. Cool and work up by removing from glove box and adding more water. Separate the aqueous and organic layers and wash aq layer with DCM. Combine all organic layers, dry on anhydrous magnesium sulfate and filter through a silica plug. Collect the orange solution which was evaporated to low volume and methanol was added to ppt a pale orange solid. Dissolve in hot toluene and run through a florisil column eluting a pale yellow band with toluene and then DCM. Evaporate to low volume and add methanol to ppt a crystalline white solid. Isolate 2.55 g material. The structure was confirmed by NMR analysis as Compound 9
Historical Records