Structure of 15546-43-7
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CAS No. : | 15546-43-7 |
Formula : | C36H28N2 |
M.W : | 488.62 |
SMILES Code : | C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 |
MDL No. : | MFCD00228123 |
InChI Key : | DCZNSJVFOQPSRV-UHFFFAOYSA-N |
Pubchem ID : | 84981 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; copper; In Soltrol/70; at 165℃; for 7h;Product distribution / selectivity; | A 5 L tri-neck round bottom flask (equipped with a mechanical stirrer, a thermal controller, and a condensing tube) was communicated with a nitrogen source and contained 500 g of dibromobiphenyl (1.6 moles), 620 g of 3-methyldiphenylamine (3.4 moles), 50 g of diphenylamine (0.3 mole), 168 g of potassium hydroxide (3 moles), 122 g of copper powder (1.76 moles) and 224 ml of Soltrol/70.(R). (fatty mixture of C13-C15 purchased from Phillips Chemical Company). The mixture solution was heated to 165° C. for 7 hours and then 2.5 L Soltrol/70.(R). was added. The temperature of the mixture solution was lowered to 154° C. to filter inorganic solids and to obtain a filtering liquid. 2 L of methanol was added to the filtering liquid to accelerate crystallization of the benzidine compounds. Then, the filtering liquid was filtered again to obtain a yellow solid, which is a crude mixture of three types of benzidine compounds. Moreover, 2 L of methanol dissolved the crude mixture of benzidine compounds and filtered by 1.2 Kg of Woelm neutral alumina to obtain a light-yellow solid. Lastly, n-octane was used to dissolve the light-yellow solid and to re-crystallize the benzidine compounds in the form of white crystal. The white crystal weighed 500 g, has a melting point range of 168-170° C., and is a final mixture of the benzidine compounds having high purity. | |
tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; at 139℃; for 6.5h;Product distribution / selectivity; | A 5 L tri-neck round bottom flask (equipped with a mechanical stirrer, a thermal controller, a condensing tube, and a Dean-Stark device) was communicated with a nitrogen source and accommodated 500 g of dibromobiphenyl (1.6 moles), 620 g of 3-methyldiphenylamine (3.4 moles), 50 g of diphenylamine (0.3 mole), 2.4 L of 10-crown-6-ether, 7.36 g of Pd2(dba)3 (0.008 mole) and 5.0 g 2,2'-bis(diphenylphosphino-1,1'-(binaphthyl) (0.008 mole). The mixture solution was stirred for 30 minutes and heated to a reflux temperature of 139° C. The mixture solution was further stirred to react for 6 hours and had further added thereto 1 L of m-xylene and 1 L of deionized water. The mixture solution was held at 65° C. and poured into an extracting bottle to place for 10 minutes until layers of the mixture solution separated. An organic layer, i.e. an m-xylene solution, was removed from the mixture solution, washed with 2 L of deionized water twice and kept at 55° C. The m-xylene solution was filtered by 600 g of Woelm neutral alumina to obtain a filtering liquid. Then, the filtering liquid was dried to obtain 630 g of a crude mixture of benzidine compounds in the form of a yellow solid. Lastly, n-octane was used to dissolve the crude mixture and to re-crystallize the benzidine compounds in the form of pure white crystal. The pure white crystal weighed 595 g, has a melting point range of 169-170° C., and is a final mixture of the benzidine compounds having high purity. | |
With calcium carbonate; zinc;1,10-Phenanthroline; copper diacetate; In xylene; at 120℃; for 10.5h;Product distribution / selectivity; | A 5 L tri-neck round bottom flask (equipped with a mechanical stirrer, a thermal controller, and a condensing tube) was communicated with a nitrogen source and contained 500 g of dibromobiphenyl (1.6 moles), 620 g of 3-methyldiphenylamine (3.4 moles), 50 g of diphenylamine (0.3 mole), 2.4 L of xylene, 27 g of 1,10-phenanthroline (0.14 mole), 420 g of cuprous acetate-monohydrate (2.1 moles), 140 g of zinc (2.1 moles) and 552 g of calcium carbonate (4 moles). The mixture solution was stirred for 30 minutes and heated to 120° C. The mixture solution was further stirred to react for 10 hours and had further added thereto 500 ml of xylene, 500 ml of deionized water and 350 g of acetic acid to neutralize calcium carbonate. The mixture solution was held at 65° C. and poured into an extracting bottle to place for 10 minutes until layers of the mixture solution separated. An organic layer, i.e. a xylene solution, was removed from the mixture solution, washed with 1.5 L of deionized water twice and kept at 55° C. The xylene solution was filtered by 500 g of Woelm neutral alumina to obtain a filtering liquid. Then, 1 L of methanol was added to the filtering liquid to accelerate crystallization of benzidine compounds to obtain 595 g crude mixture of benzidine compounds in the form of a white solid. Lastly, n-octane was used to dissolve the crude mixture and to re-crystallize the benzidine compounds in the form of pure white crystal. The pure white crystal weighed 545 g, has a melting point range of 169-170° C., and is a final mixture of the benzidine compounds having high purity |
With potassium hydroxide;1,10-Phenanthroline; copper dichloride; In toluene; at 125℃; for 6.5h;Product distribution / selectivity; | A 5 L tri-neck round bottom flask (equipped with a mechanical stirrer, a thermal controller, and a condensing tube) was communicated with a nitrogen source and contained 500 g of dibromobiphenyl (1.6 moles), 620 g of 3-methyldiphenylamine (3.4 moles), 50 g of diphenylamine (0.3 mole), 24 L of toluene, 27 g of 1,10-phenanthroline (0.14 mole), 16 g of cuprous chloride (0.14 mole) and 168 g potassium hydroxide (3 moles). The mixture solution was stirred for 30 minutes and heated to 125° C. The mixture solution was further stirred to react for 6 hours and had added thereto 500 ml of toluene, 500 ml of deionized water and 400 g of acetic acid to neutralize the potassium hydroxide. The mixture solution was held at 70° C. and then poured into an extracting bottle to place for 10 minutes until layers of the mixture solution separated. An organic layer, i.e. a toluene solution, was removed from the mixture solution, washed with 1 L of deionized water twice and kept at 60° C. The toluene solution was filtered by 500 g of Woelm neutral alumina to obtain a filtering liquid. Then, the filtering liquid was dried to obtain 605 g of a crude mixture of benzidine compounds in the form of a white solid. Lastly, n-octane was used to dissolve the crude mixture and to re-crystallize the benzidine compounds in the form of pure white crystal. The pure white crystal weighed 500 g, has a melting point range of 169-170° C., and is a final mixture of the benzidine compounds having high purity. | |
With potassium hydroxide;1,10-Phenanthroline; copper dichloride; In m-xylene; at 139℃; for 7.5h;Heating / reflux;Product distribution / selectivity; | A 5 L tri-neck round bottom flask (equipped with a mechanical stirrer, a thermal controller, a condensing tube, and a Dean-Stark device) was communicated with a nitrogen source and accommodated 500 g of dibromobiphenyl (1.6 moles), 620 g of 3-methyldiphenylamine (3.4 moles), 50 g of diphenylamine (0.3 mole), 2.4 L of m-xylene, 27 g of 1,10-phenanthroline (0.14 mole), 16 g of cuprous chloride (0.14 mole) and 168 g potassium hydroxide (3 moles). The mixture solution was stirred for 30 minutes and heated to a reflux temperature of 139° C. The mixture solution was further stirred to react for 7 hours and had further added thereto 1 L of m-xylene, 1 L of deionized water and 400 g of acetic acid to neutralize the potassium hydroxide. The mixture solution was held at 65° C. and poured into an extracting bottle to place for 10 minutes until layers of the mixture solution separated. An organic layer, i.e. an m-xylene solution, was removed from the mixture solution, washed with 2 L of deionized water twice and kept at 55° C. The m-xylene solution was filtered by 600 g of Woelm neutral alumina to obtain a filtering liquid. Then, the filtering liquid was dried to obtain 610 g of a crude mixture of benzidine compounds in the form of a Elite solid. Lastly, n-octane was used to dissolve the crude mixture and to re-crystallize the benzidine compounds in the form of pure white crystal. The pure white crystal weighed 585 g, has a melting point range of 169-170° C., and is a final mixture of the benzidine compounds having high purity. | |
With potassium hydroxide;1,10-Phenanthroline; copper dichloride; In xylene; at 145℃; for 7.5h;Heating / reflux;Product distribution / selectivity; | A 5 L tri-neck round bottom flask (equipped with a mechanical stirrer, a thermal controller, a condensing tube, and a Dean-Stark device) was communicated with a nitrogen source and accommodated 500 g of dibromobiphenyl (1.6 moles), 620 g of 3-methyldiphenylamine (3.4 moles), 50 g of diphenylamine (0.3 mole), 2.4 L of xylene, 27 g of 1,10-phenanthroline (0.14 mole), 16 g of cuprous chloride (0.14 mole) and 168 g of potassium hydroxide (3 moles). The mixture solution was stirred for 30 minutes and heated to a reflux temperature of 145° C. The mixture solution was further stirred to react for 7 hours and had further added thereto 1 L of o-xylene, 1 L of deionized water and 400 g of acetic acid to neutralize the potassium so hydroxide. The mixture solution was held at 100° C. and poured into an extracting bottle to place for 10 minutes until layers of the mixture solution separated. An organic layer, i.e. an o-xylene solution, was removed from the mixture solution, washed with 1.5 L of deionized water twice and kept at 70° C. The o-xylene solution was filtered by 20 g of Alcoa-C neutral alumina to obtain a filtering liquid. Then, the filtering liquid was dried to obtain 615 g of a crude mixture of benzidine compounds in the form of a white solid. Lastly, n-octane was used to dissolve the crude mixture and to re-crystallize the benzidine compounds in the form of pure white crystal. The pure white crystal weighed 600 g, has a melting point range of 168-170° C., and is a final mixture of the benzidine compounds having high purity. | |
With potassium hydroxide; 18-crown-6 ether; copper; In m-xylene; at 139℃; for 10.5h;Product distribution / selectivity; | A 5 L tri-neck round bottom flask (equipped with a mechanical stirrer, a thermal controller, and a condensing tube) was communicated with a nitrogen source and contained 500 g of dibromobiphenyl (1.6 moles), 620 g of 3-methyldiphenylamine (3.4 moles), 50 g of diphenylamine (0.3 mole), 2.4 L of m-xylene (0.14 mole), 150 g of copper powder (2.4 moles), 168 g potassium hydroxide (3 moles) and 35 g of 18-crown-6-ether. The mixture solution was stirred for 30 minutes and heated to a reflux temperature of 139° C. The mixture solution was further stirred to react for 10 hours and had further added thereto 1 L of m-xylene, 1 L of deionized water and 400 g of acetic acid to neutralize the potassium hydroxide. The mixture solution was held at 65° C. and poured into an extracting bottle to place for 10 minutes until layers of the mixture solution separated. An organic layer, i.e. an m-xylene solution, was removed from the mixture solution, washed with 2 L of deionized water twice and kept at 55° C. The m-xylene solution was filtered by 600 g of Woelm neutral alumina to obtain a filtering liquid. Then, the filtering liquid was dried to obtain 620 g of a crude mixture of benzidine compounds in the form of a white solid. Lastly, n-octane was used to dissolve the crude mixture and to re-crystallize the benzidine compounds in the form of pure white crystal. The pure white crystal weighed 600 g, has a melting point range of 169-170° C., and is a final mixture of the benzidine compounds having high purity. | |
With potassium hydroxide; copper; In Soltrol/170; at 190℃; for 10.5h;Product distribution / selectivity; | A 5 L tri-neck round bottom flask (equipped with a mechanical stirrer, a thermal controller, and a condensing tube) was communicated with a nitrogen source and accommodated 500 g of dibromobiphenyl (1.6 moles), 620 g of 3-methyldiphenylamine (3.4 moles), 50 g of diphenylamine (0.3 mole), 2 L of Soltrol.(R)./170, 150 g of copper powder (2.4 moles) and 168 g potassium hydroxide (3 moles). The mixture solution was stirred for 30 minutes and heated to 190° C. The mixture solution was further stirred to react for 10 hours and had further added thereto 1 L of toluene, 1.5 L of deionized water and 400 g of acetic acid to neutralize the potassium hydroxide. The mixture solution was held at 65° C. and poured into an extracting bottle to place for 10 minutes until layers of the mixture solution separated. An organic layer, i.e. a toluene solution, was removed from the mixture solution, washed with 2 L of deionized water twice and kept at 55° C. The toluene solution was filtered by 500 g of Woelm neutral alumina to obtain a filtering liquid. Then, the filtering liquid was dried to obtain 630 g of a crude mixture of benzidine compounds in the form of a white solid. Lastly, n-octane was used to dissolve the crude mixture and to re-crystallize the benzidine compounds in the form of pure white crystal. The pure white crystal weighed 600 g, has a melting point range of 167-170° C., and is a final mixture of the benzidine compounds having high purity. | |
With sodium t-butanolate;palladium diacetate; tri-tert-butyl phosphine; In xylene; at 125℃; for 5.5h;Product distribution / selectivity; | A 5 L tri-neck round bottom flask (equipped with a mechanical stirrer, a thermal controller, a condensing tube, and a Dean-Stark device) was communicated with a nitrogen source and accommodated 500 g of dibromobiphenyl (1.6 moles), 620 g of 3-methyldiphenylamine (3.4 moles), 50 g of diphenylamine (0.3 mole), 2.5 L of xylene, 0.183 g of Pd(OAc)2 (0.051 mole), 0.14 g of P(t-Bu)3 (0.043 mole) and 350 g NaO-(t-Bu) (3.64 mole). The mixture solution was stirred for 30 minutes and heated to a reflux temperature of 125° C. The mixture solution was further stirred to react for 5 hours and had further added thereto 500 ml of o-xylene and 500 ml of deionized water. The mixture solution was held at 65° C. and poured into an extracting bottle to place for 10 minutes until layers of the mixture solution separated. An organic layer, i.e. an o-xylene solution, was removed from the mixture solution, washed with 1 L of deionized water twice and kept at 55° C. The o-xylene solution was filtered by 500 g of Woelm neutral alumina to obtain a filtering liquid. Then, the filtering liquid was dried to obtain 660 g of a crude mixture of benzidine compounds in the form of a white solid. Lastly, n-octane was used to dissolve the crude mixture and to re-crystallize the benzidine compounds in the form of pure white crystal. The pure white crystal weighed 580 g, has a melting point range of 168-170° C., and is a final mixture of the benzidine compounds having high purity. | |
With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 110℃; for 5.5h;Product distribution / selectivity; | A 5 L tri-neck round bottom flask (equipped with a mechanical stirrer, a thermal controller, a condensing tube, and a Dean-Stark device) was communicated with a nitrogen source and accommodated 500 g of dibromobiphenyl (1.6 moles), 620 g of 3-methyldiphenylamine (3.4 moles), 50 g of diphenylamine (0.3 mole), 2.4 L of toluene, 7.36 g of Pd2(dba)3 (0.008 mole) (prepared according to J. Org. Chem. 2000,65,p.5330) and 350 g NaO-(t-Bu) (3.64 mole). The mixture solution was stirred for 30 minutes and heated to a reflux temperature of 110° C. The mixture solution was further stirred to react for 5 hours and had further added thereto 500 ml of toluene and 500 ml of deionized water. The mixture solution was held at 55° C. and poured into an extracting bottle to place for 10 minutes until layers of the mixture solution separated. An organic layer, i.e. a toluene solution, was removed from the mixture solution, washed with 2 L of deionized water twice and kept at 55° C. The toluene solution was filtered by using 500 g of Woelm neutral alumina to obtain a filtering liquid. Then, the filtering liquid was dried to obtain 650 g of a crude mixture of benzidine compounds in the form of a yellow solid. Lastly, n-octane was used to dissolve the crude mixture and to re-crystallize the benzidine compounds in the form of pure white crystal. The pure white crystal weighed 550 g, has a melting point range of 169-170° C., and is a final mixture of the benzidine compounds having high purity. |
Tags: 15546-43-7 synthesis path| 15546-43-7 SDS| 15546-43-7 COA| 15546-43-7 purity| 15546-43-7 application| 15546-43-7 NMR| 15546-43-7 COA| 15546-43-7 structure
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H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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