Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrazine In ethanol for 6h; Inert atmosphere; Reflux; | 100% |
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 18h; | 99% |
With 3% Pd/C; hydrazine In ethanol Heating; | 77% |
1.4-dibromobenzene
4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline
4,4''-diamino-p-terphenyl
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Schlenk technique; Inert atmosphere; Heating; | 52% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Schlenk technique; Inert atmosphere; Heating; | 52% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 110℃; for 48h; Inert atmosphere; | 48% |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 76 percent / K2CO3 / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 18 h / Heating 2: 99 percent / H2 / Pd/C / tetrahydrofuran / 18 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 76 percent / K2CO3 / tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 18 h / Heating 2: 99 percent / H2 / Pd/C / tetrahydrofuran / 18 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: fuming HNO3 / acetic acid 2: SnCl2, aq. HCl View Scheme | |
Multi-step reaction with 2 steps 1: HNO3 / acetic acid 2: H2, Py / Raney-Ni / 100 °C / 60800 - 65360 Torr View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; sulfuric acid / 60 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 48 h / Reflux; Inert atmosphere 3: palladium 10% on activated carbon; hydrazine / ethanol / 6 h / Inert atmosphere; Reflux View Scheme |
3,5-dinitrobromobenzene
4,4''-diamino-p-terphenyl
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran / 48 h / Reflux; Inert atmosphere 2: palladium 10% on activated carbon; hydrazine / ethanol / 6 h / Inert atmosphere; Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 12 h / 120 °C / Schlenk technique; Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene / 24 h / Schlenk technique; Inert atmosphere; Heating View Scheme | |
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 1,4-dioxane / 12 h / 120 °C / Schlenk technique; Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene / 24 h / Schlenk technique; Inert atmosphere; Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / Heating 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / Heating 3: hydrazine; 3% Pd/C / ethanol / Heating View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium acetate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine / 1,4-dioxane / 4.33 h / 110 °C 2.1: potassium carbonate / tetrahydrofuran; water / 0.33 h / 100 °C 2.2: 5 h / 100 °C 3.1: hydrazine; 3% Pd/C / ethanol / 12 h / 100 °C View Scheme |
benzene-1,4-diboronic acid bispinacol ester
4,4''-diamino-p-terphenyl
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / tetrahydrofuran; water / 0.33 h / 100 °C 1.2: 5 h / 100 °C 2.1: hydrazine; 3% Pd/C / ethanol / 12 h / 100 °C View Scheme |
4,4''-diamino-p-terphenyl
2-hydroxynaphthalene-1-carbaldehyde
1,1'-[(4,4''-p-terphenylene)bis(iminomethyl)]bis(2-naphthol)
Conditions | Yield |
---|---|
With formic acid In methanol; dichloromethane Reflux; | 98% |
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; potassium tert-butylate; bis(dibenzylideneacetone)-palladium(0) In toluene at 80℃; for 69.5h; Inert atmosphere; | 97% |
3,5-di-tert-butyl-2-hydroxybenzaldehyde
4,4''-diamino-p-terphenyl
Conditions | Yield |
---|---|
With formic acid In methanol; dichloromethane Reflux; | 93% |
3-tert-butyl-2-hydroxybenzaldehyde
4,4''-diamino-p-terphenyl
Conditions | Yield |
---|---|
With formic acid In methanol; dichloromethane Reflux; | 91% |
4,4''-diamino-p-terphenyl
Ethoxycarbonyl isothiocyanate
4,4''-bis(N'-ethoxycarbonylthiourea)-[1,1';4',1'']terphenyl
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 24h; | 89% |
4,4''-diamino-p-terphenyl
4,4''-bis(N'-ethoxycarbonylthiourea)-[1,1';4',1'']terphenyl
Conditions | Yield |
---|---|
With Ethoxycarbonyl isothiocyanate In dichloromethane at 20℃; for 24h; | 89% |
Conditions | Yield |
---|---|
With formic acid In methanol; dichloromethane Reflux; | 84% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 5h; Inert atmosphere; Reflux; | 83.6% |
4,4''-diamino-p-terphenyl
N,N'-bis-Boc-S-methyl-isothiourea
Conditions | Yield |
---|---|
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃; for 24h; | 79% |
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃; for 24h; | 79% |
4,4''-diamino-p-terphenyl
Conditions | Yield |
---|---|
Stage #1: 4,4''-diamino-p-terphenyl With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Cooling with ice; Stage #2: With sodium azide In water at 0℃; for 2h; Cooling with ice; | 78.1% |
Stage #1: 4,4''-diamino-p-terphenyl With sodium nitrite In water for 2h; Stage #2: With sodium azide In water for 2h; | 45.6% |
4,4''-diamino-p-terphenyl
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; triethylamine In tetrahydrofuran at 20℃; for 6h; | 75% |
4,4''-diamino-p-terphenyl
ethyl iodide
N,N-dimethyl-formamide
p,p"-bis-diethylamino-p-terphenyl
Conditions | Yield |
---|---|
With calcium carbonate In N-methyl-acetamide; water | 70% |
Conditions | Yield |
---|---|
With propionic acid at 150℃; for 10h; | 70% |
4,4''-diamino-p-terphenyl
Conditions | Yield |
---|---|
With potassium dichromate; perchloric acid; acetic acid In water | 55.5% |
4,4''-diamino-p-terphenyl
Conditions | Yield |
---|---|
In tetrahydrofuran Schlenk techniques used, 7c (0.32 mmol) added to THF soln. of 5a (0.16 mmol) in THF under Ar, stirred for 2 h at room temp.; solvent removed under vac., chromd. (SiO2, hexane/AcOEt) under Ar pressure; elem. anal.; | 47% |
Conditions | Yield |
---|---|
With sodium t-butanolate; bis-triphenylphosphine-palladium(II) chloride In xylene at 130℃; for 24h; | 41% |
2'-bromo(spiro[cyclohexane-1,9'[9H]fluoren])
4,4''-diamino-p-terphenyl
Conditions | Yield |
---|---|
With sodium t-butanolate; bis-triphenylphosphine-palladium(II) chloride In xylene at 130℃; for 24h; | 36% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide tren (2 mmol) added to soln. of Cu(ClO4)2*6H2O (2 mmol) under stirring, NH2(C6H4)3NH2 (1 mmol) soln. added dropwise; soln. filtered off, Et2O slow diffused into soln., crystd. for one week at room temp., collected, air dried; elem. anal.; | 31% |
Conditions | Yield |
---|---|
In various solvent(s) for 3h; Condensation; Heating; | 20% |
Conditions | Yield |
---|---|
Stage #1: 4,4''-diamino-p-terphenyl; α-chlorobenzaldehyde phenylhydrazone With triethylamine In tetrahydrofuran for 24h; Reflux; Stage #2: With palladium 10% on activated carbon; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 24h; | 14% |
4,4''-diamino-p-terphenyl
Conditions | Yield |
---|---|
With Na In toluene soln. of Mo-complex and ligand in toluene contg. Na was heated under reflux, stirred for 18 h under N2, cooled; filtered, solvent was removed in vacuo, sepd. by column chromy. with CH2Cl2/hexane; elem. anal.; | 2% |
Conditions | Yield |
---|---|
With acetic acid In toluene for 48h; Knorr Pyrazole Synthesis; Inert atmosphere; Reflux; | |
In acetic acid; toluene at 130℃; for 72h; Inert atmosphere; | 0.24% |
Conditions | Yield |
---|---|
With hydrogenchloride Diazotization.Einleiten von Wasserdampf; |
4,4''-diamino-p-terphenyl
phenyl Salicylate
N,N'-p-terphenyl-4,4''-diyl-bis-salicylamide
Conditions | Yield |
---|---|
With 1-Methylnaphthalene |
4,4''-diamino-p-terphenyl
2-Methoxybenzoyl chloride
4,4''-Bis-(2-methoxy-benzoylamino)-p-terphenyl
Conditions | Yield |
---|---|
With pyridine |
The 4,4''-Diamino-p-terphenyl, with the CAS registry number 3365-85-3, has the systematic name of 1,1':4',1''-terphenyl-4,4''-diamine. And the molecular formula of the chemical is C18H16N2.
The characteristics of this chemical are as followings: (1)ACD/LogP: 3.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.17; (4)ACD/LogD (pH 7.4): 3.22; (5)ACD/BCF (pH 5.5): 146.69; (6)ACD/BCF (pH 7.4): 164.73; (7)ACD/KOC (pH 5.5): 1196.24; (8)ACD/KOC (pH 7.4): 1343.32; (9)#H bond acceptors: 2; (10)H bond donors: 4; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 6.48 Å2; (13)Index of Refraction: 1.67; (14)Molar Refractivity: 83.9 cm3; (15)Molar Volume: 224.5 cm3; (16)Polarizability: 33.26×10-24cm3; (17)Surface Tension: 52.9 dyne/cm; (18)Density: 1.159 g/cm3; (19)Flash Point: 296.3 °C; (20)Enthalpy of Vaporization: 74.95 kJ/mol; (21)Boiling Point: 484.2 °C at 760 mmHg; (22)Vapour Pressure: 1.57E-09 mmHg at 25°C.
You should be very cautious while dealing with this chemical. It is harmful by inhalation, in contact with skin and if swallowed, and it may cause cancer. Therefore, you had better take the following instructions: Avoid exposure - obtain special instruction before use; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: c3c(c1ccc(N)cc1)ccc(c2ccc(N)cc2)c3
(2)InChI: InChI=1/C18H16N2/c19-17-9-5-15(6-10-17)13-1-2-14(4-3-13)16-7-11-18(20)12-8-16/h1-12H,19-20H2
(3)InChIKey: QBSMHWVGUPQNJJ-UHFFFAOYAO
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