Home Cart 0 Sign in  

[ CAS No. 123847-85-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 123847-85-8
Chemical Structure| 123847-85-8
Structure of 123847-85-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 123847-85-8 ]

Related Doc. of [ 123847-85-8 ]

Alternatived Products of [ 123847-85-8 ]

Product Details of [ 123847-85-8 ]

CAS No. :123847-85-8 MDL No. :MFCD03093246
Formula : C44H32N2 Boiling Point : -
Linear Structure Formula :- InChI Key :IBHBKWKFFTZAHE-UHFFFAOYSA-N
M.W : 588.74 Pubchem ID :5069127
Synonyms :
UV :339 nm (in THF)
FL :450 nm (in THF) Materials Type :HTM

Calculated chemistry of [ 123847-85-8 ]

Physicochemical Properties

Num. heavy atoms : 46
Num. arom. heavy atoms : 44
Fraction Csp3 : 0.0
Num. rotatable bonds : 7
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 196.26
TPSA : 6.48 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -1.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 6.1
Log Po/w (XLOGP3) : 12.52
Log Po/w (WLOGP) : 12.6
Log Po/w (MLOGP) : 8.83
Log Po/w (SILICOS-IT) : 8.98
Consensus Log Po/w : 9.81

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -11.62
Solubility : 0.0000000014 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (Ali) : -12.68
Solubility : 0.0000000001 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -16.72
Solubility : 0.0 mg/ml ; 1.91e-17 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.61

Safety of [ 123847-85-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 123847-85-8 ]

* 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.

  • Downstream synthetic route of [ 123847-85-8 ]

[ 123847-85-8 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 92-86-4 ]
  • [ 90-30-2 ]
  • [ 123847-85-8 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: N-phenyl-1-naphthylamine With n-butyllithium Stage #2: 4-(4-bromophenyl)bromobenzene With bis[tris(2-methylphenyl)phosphine]palladium In toluene at 100℃;
92% With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In o-xylene at 120℃; for 3h;
  • 2
  • [ 90-11-9 ]
  • [ 531-91-9 ]
  • 4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With sodium t-butanolate;palladium diacetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; In toluene; at 20 - 130℃;Inert atmosphere; 1.5 g (15 mmol) of sodium tert-butoxide, 110 mg (0.25 mmol) of IPr-HCl (compound No. 1), 26 mg (0.1 mmol) of palladium(II) acetate, 1.68 g (5 mmol) of N,N'-diphenylbenzidine, 2.56 g (12 mmol) of 1-bromonaphthalene and 30 ml of toluene were put into a 100-ml three-neck flask equipped with a stirrer, a condenser tube, a thermometer and a gas-introducing duct, in an argon current at room temperature, and reacted under reflux in an oil bath controlled at a temperature of 130C for 14 hours. The reaction liquid was cooled to room temperature, then left overnight at room temperature, and 150 ml of methylene chloride was added thereto. The insoluble matter was removed by filtration, and the filtrate was washed twice with 50 ml of water. This was dewatered and dried with 30 g of anhydrous sodium sulfate, and the solvent was evaporated away to give a residue. The residue was purified through column chromatography (carrier, Fuji Silicia's NH silica gel 150 g; eluent, cyclohexane) to give 2.8 g of N,N'-diphenyl-N,N'-dinaphthylbenzidine (NPD) (yield 95%).
70% With tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 12h;Inert atmosphere; Reflux; Compound Ref-2-1 (16.8 g, 50 mmol) and Compound Ref-2-2 (20.7 g, 100 mmol), (2.3 g, 2.5 mmol), tri-tert-butylphosphine (1 g, 5 mmol) and sodium tert-butoxide (9.6 g, 100 mmol) and toluene (150 mL) were added into a 250 mL two-necked flask under nitrogen atmosphere, and the mixture was refluxed with heating and reacted under stirring for 12 hours, and then the reaction was ended. The reaction solution was distilled under reduced pressure to remove most of the solvent, and then dissolved with dichloromethane and washed with water for 3 times. The organic solution was collected, mixed with silica gel, and purified by column chromatography, with a yield of 70%.
  • 3
  • [ 73039-27-7 ]
  • [ 92-86-4 ]
  • [ 123847-85-8 ]
YieldReaction ConditionsOperation in experiment
35% With tri-tert-butyl phosphine; caesium carbonate; cesium fluoride In hexane at 100℃; for 48h;
  • 4
  • [ 90-30-2 ]
  • [ 123847-85-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 1.2: 53 percent / tetrahydrofuran; hexane / 18 h / 20 °C 2.1: 35 percent / P(t-Bu)3; Cs2CO3; CsF / Pd2dba3; scCO2 / hexane / 48 h / 100 °C / 93086.6 Torr
Multi-step reaction with 2 steps 1: sodium sulfate; potassium carbonate; copper / nitrobenzene 2: tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate / toluene / 24 h / 100 °C
  • 5
  • [ 3001-15-8 ]
  • [ 90-30-2 ]
  • 4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
55.9% With copper; potassium carbonate;PEG-6000; at 200 - 250℃; for 12h;Heating / reflux; Neat (no solvent); (Synthetic Example 4) N,N'-diphenyl-bis(1-naphthyl)-4,4'-diaminobiphenyl (alpha-NPD) was synthesized as follows. 25.1g (61.5mmol) of 4,4'-diiodobiphenyl, 2.14g of poly(ethylene glycol) PEG-6000 that was available from Wako Pure Chemical Industries, Ltd., 17.1g (0.124mol) of potassium carbonate and 15.7g (247mmol) of powdered copper were added to 32.4g (148mmol) of <strong>[90-30-2]N-phenyl-1-naphthylamine</strong>. It was heated at 200 degrees Centigrade. It was determined for tracing by the high-speed liquid chromatography. And it was stirred and refluxed for 12 hours until no peaks of starting materials and intermediates were determined. DMF and water were added thereto to disperse. It was filtrated and washed with water. Precipitated crystals were purified by silica gel column chromatography to obtain 20.2g of alpha-NPD that is represented by Compound Example 4 at 55.9% yield. Incidentally, when the similar procedures of Synthetic Example 4 were executed except for using 1.57g of powdered copper and heating at 250 degrees Centigrade, the same alpha-NPD was obtained.
45.0% With copper; potassium carbonate; In nitrobenzene; at 195 - 210℃; for 20h; N,N'-di(1-naphtyl)-N,N'-diphenylbenzidine 4.6 g (0.021 moles) of (1-naphtyl)phenylamine, 4.06 g (0.01 mole) of 4,4'-diiodobiphenyl, 2.90 g (0.021 moles) of anhydrous potassium carbonate, 0.32 g (0.005 moles) of copper powders and 10 ml of nitrobenzene were mixed, and the mixture was reacted at 195 to 210 C. for 20 hours. The reaction product was extracted with 140 ml of toluene, the insoluble was filtered off, and the filtrate was concentrated. 120 ml of n-hexane was added to the concentrated product to obtain a raw product. The raw product was purified on a column chromatography using silica gel as a carrier and toluene/n-hexane (1/2) as an eluding solution to obtain 2.6 g (yield: 45.0%) of N,N'-di(1-naphtyl)-N,N'-diphenylbenzidine.
  • 6
  • [ 3001-15-8 ]
  • [ 90-30-2 ]
  • [ 107-21-1 ]
  • [ 123847-85-8 ]
YieldReaction ConditionsOperation in experiment
55.9% With copper; potassium carbonate In water; N,N-dimethyl-formamide 5 Synthesis of N,N'-di(1-naphthyl)-N,N'-diphenyl-4,4'-diaminobiphenyl (α-NPD) EXAMPLE 5 Synthesis of N,N'-di(1-naphthyl)-N,N'-diphenyl-4,4'-diaminobiphenyl (α-NPD) To 32.4 g (148 mmol) of N-phenyl-1-naphthylamine were added 25.1 g (61.5 mmol) of 4,4'-diiodobiphenyl, 2.14 g of polyethylene glycol (PEG-6000 (a trade name) manufactured by Wako Junyaku K.K.), 17.1 g (0.124 mol) of potassium carbonate and 15.7 g (247 mmol) of copper (powder) were added, and heated to 200° C. The reaction was traced by high-performance liquid chromatography. Heating was continued under stirring until the peaks of raw materials and intermediates were disappeared (for 12 hours). After the completion of the reaction, water and DMF are added, and the resulting mixture is dispersed, filtrated, and washed with water. The resulting crystal is purified by silica gel chromatography to afford 20.2 g (yield: 55.9%) of N,N'-di(l-naphthyl)-N,N'-diphenyl-4,4'-diaminobiphenyl represented by the formula: The IR analysis is shown in FIG. 5. The 1H-NMR spectrum, 13C-NMR spectrum and FD-MS spectrum are shown in FIGS. 6, 7and 8, respectively.
  • 7
  • [ 2077-19-2 ]
  • 4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl [ No CAS ]
  • N4,N4'-bis(4-(2-(4-bromophenyl)propan-2-yl)phenyl)-N4,N4'-di(naphthalen-1-yl)biphenyl-4,4'-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
8.1 g With diethyl ether; boron trifluoride; In dichloromethane; at 20℃;Inert atmosphere; In a 250ml 2 necked round-bottom flask equipped with a condenser and under argon were dissolved 5.3g of N4,N4'-di(naphthalen-1 -yl)-N4,N4'- diphenylbiphenyl-4,4'-diamine (NPD) and 4.2g of 2(4-bromophenyl-2- propanol) in 65ml of dichloromethane. Then 3.15ml of BF3, Et.20 were added dropwise under stirring at room temperature. The reaction was monitored by thin layer chromatography (TLC). After completion, the reaction medium was filtered through a silica gel plug. The plug was rinsed by 25ml of dichloromethane. After removal of the solvent under reduced pressure crude product was recovered and purified by flash chromatography over silica gel using a mixture of 50/50 v/v hexane/dichloro methane as the eluent. 8.1 g of pure N4,N4'-bis(4-(2-(4- bromophenyl)propan-2-yl)phenyl)-N4,N4'-di(naphthalen-1 -yl)biphenyl-4,4'- diamine was obtained. Structure was confirmed by NMR.
  • 8
  • [ 68-12-2 ]
  • [ 123847-85-8 ]
  • [ 847690-55-5 ]
YieldReaction ConditionsOperation in experiment
45% With trichlorophosphate In 1,2-dichloro-ethane at 0 - 50℃; for 7h; Inert atmosphere; 1.1 1) Synthesis of NPD-CHO (NPD comprising an aldehyde group) Example 1 1) Synthesis of NPD-CHO (NPD comprising an aldehyde group) At 0°C, under nitrogen protection, POCl3 (6.0g) is added to DMF (2.5g), followed by the addition of NPD (11.0g) in 120 ml 1,2-dichloroethane, and the mixture heated to 50°C for 7 hours. After cooling, the reaction mixture is added into 500 ml water, and extracted with ethyl acetate. The organic layer is neutralized with aqueous NaCO3 solution. Finally isolation is conducted by silica gel chromatography using a petroleum ether/ethyl acetate (with a volume ratio of 10:1) mixed solvent as the developing solvent, to give NPD-CHO, and the yield is 45%.
  • 9
  • [ 352359-42-3 ]
  • [ 90-30-2 ]
  • 4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 100℃; for 24h; N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine (10.8g, 24mmol) was dissolved in toluene, N-phenylnaphthalen-1-amine (4.4 g, 20mmol), Pd2(dba)3 (0.05 equiv), PPh3 (0.1 equiv.), were added to each of NaOt-Bu (3 eq.), stirred and refluxed for 24 hours at 100 C. After the reaction was terminated and the resulting organic material was extracted and the organic layer was dried over MgSO4 and concentrated in ether and water silicagel column and the final compound was recrystallized 11.4g (yield: 81%) was obtained.
81% With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 100℃; for 24h; N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine (10.8g, 24mmol) was dissolved in toluene, N-phenylnaphthalen-1-amine (4.4g,20mmol), Pd2 (dba) 3 (0.05 eq.), PPh3 (0.1 eq.) and NaOt-Bu (3 eq.) were added, stirred at 100 degree C and refluxed for 24 hours. After completion of the reaction, the organic layer was extracted with water and ether, and the resulting compound was purified by silica gel column, then concentrated, dried over MgSO4 and recrystallized to give the final compound 11.4g (yield: 81%).
81% With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 100℃; for 24h; N-(4?-bromo-[1,1?-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine (10.8 g, 24 mmol) was dissolved in toluene and, N-phenylnaphthalen-1-amine (4.4 g, 20 mmol), Pd2(dba)3 (0.05 eq.), PPh3 (0.1 eq.), NaOt-Bu (3 eq.) were added and refluxed with stirring at 100 C. for 24 hours. When the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 11.4 g (yield: 81%) of the product.
  • 10
  • [ 717888-41-0 ]
  • [ 138310-84-6 ]
  • 4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In water; toluene; at 85℃; for 24h;Inert atmosphere; After nitrogen replacement in a 200 ml eggplant flask equipped with a thermometer and a condenser,3.74 g (0.010 mol) of N-phenyl-N- (4-bromophenyl) -1-naphthylamine,3.73 g (0.011 mol) of N-phenyl-N- (4-boronic acid phenyl) -1-naphthylamine,10.6 g (0.050 mol) of tripotassium phosphate,20.0 g (1.11 mol) of pure water, 50.0 g (0.543 mol) of toluene,0.046 g (0.05 μmol) of tris dibenzylidene acetone dipalladium,0.061 g (0.30 μmol) of tri-tert-butylphosphine was charged.The reaction vessel was heated to 85 C. and then stirred for 24 hours. After adding 50.0 g of water, the mixture was cooled to a temperature of 25 C. and filtered to obtain 5.83 g (isolation yield: 99%) of crude NPD as a product.HPLC analysis of NPD and remaining halogenated compounds as raw materials showed purity of 97.7% and 1.6%, respectively.After heating the reaction vessel to a temperature of 140 C., 5.0 g of a N, N-dimethylacetamide solution containing 168 mg (0.75 mmol) of palladium acetate and 28.4 mg (0.75 mmol) of sodium borohydride was added , And stirred for 1 hour.The reaction solution was collected and analyzed by HPLC. As a result, the remaining raw material halogen compound was not detected.The reaction solution was cooled to a temperature of 25 C. and filtered to obtain 5.59 g of NPD (isolation yield: 95%). HPLC analysis of NPD and the halogen compound of the remaining raw material showed purity of 97.8%, undetected, respectively.Then, recrystallization of the obtained NPD was performed twice using N, N-dimethylacetamide (15 wt.r) and o-xylene (15 wt. R), and 5.05 g of NPD was isolated in isolated yield 85 %. HPLC analysis of NPD and remaining raw material halogen compounds revealed purity of 99.9%, undetected respectively. These results are shown in Table 1.
Same Skeleton Products
Historical Records