1,2-bis(2-nitrophenoxy)ethane
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In N,N-dimethyl-formamide at 70 - 80℃; for 20h; | 95.6% |
With hydrazine hydrate; palladium on activated charcoal In ethanol for 2h; Heating; | 94% |
With hydrazine hydrate; palladium on activated charcoal In ethanol for 2h; Heating; | 91% |
1,2-bis-(2-acetylamino-phenoxy)-ethane
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
bei der Destillation; |
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
With hydrogenchloride; tin |
sodium o-nitrophenate
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dimethylformamide 2: H2 / Pd/C / ethanol View Scheme | |
Multi-step reaction with 2 steps 1: dimethylformamide / 2 h / Heating 2: 10percent Pd/C / ethanol View Scheme | |
Multi-step reaction with 2 steps 1: ethylene glycol / 150 °C 2: Raney nickel; ethanol / Hydrogenation View Scheme | |
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide 2: hydrogen; palladium on activated charcoal / methanol View Scheme |
2-hydroxynitrobenzene
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaOH / ethanol 2: dimethylformamide / 2 h / Heating 3: 10percent Pd/C / ethanol View Scheme |
2-hydroxynitrobenzene
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / K2CO3 (calcined) / dimethylsulfoxide / 6 h / 130 °C 2: 91 percent / 85percent NH2NH2*H2O / 5percent Pd/C / ethanol / 2 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: K2CO3 2: SnCl2*2H2O, aq. HCl View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 130 °C / Inert atmosphere 2: hydrogen / 5%-palladium/activated carbon / dichloromethane; ethanol / 25 °C View Scheme |
1-(2-chloroethoxy)-2-nitrobenzene
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 - 140 °C 2: iron; hydrogenchloride / ethanol / 4 h / Reflux View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol Reflux; |
1,2-Bis(2-aminophenoxy)ethane
orthoformic acid triethyl ester
Conditions | Yield |
---|---|
With sodium azide; acetic acid at 90℃; | 99% |
1,2-Bis(2-aminophenoxy)ethane
5-(acetoacetamido)-2-benzimidazolinone
Conditions | Yield |
---|---|
Stage #1: 1,2-Bis(2-aminophenoxy)ethane With hydrogenchloride; sodium nitrite In water at 5℃; Large scale; Stage #2: 5-Acetoacetyl-amino-benzimidazol-2-one With acetic acid; sodium hydroxide In water at 5℃; pH=7; Large scale; Stage #3: With sodium hydrogencarbonate In water for 3h; pH=7; Reagent/catalyst; Solvent; Large scale; | 95.8% |
1,1'-bis(isothiocyanatocarbonyl)ferrocene
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
In water; acetone at 20℃; for 5h; | 89.2% |
1,2-Bis(2-aminophenoxy)ethane
phenyl isothiocyanate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Addition; | 88.2% |
diglycolyl chloride
1,2-Bis(2-aminophenoxy)ethane
17,18-dihydro-5H,9H-dibenzo[e,n]1,4,10,7,13trioxadiazacyclopentadecine-6,10-(7H,11H)-dione
Conditions | Yield |
---|---|
With pyridine In benzene at 75℃; for 3h; | 87% |
1,2-Bis(2-aminophenoxy)ethane
bromoacetic acid methyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile for 24h; Reflux; | 87% |
3,5-di-tert-butyl-2-hydroxybenzaldehyde
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
With acetic acid In ethanol for 12h; Reflux; Inert atmosphere; Schlenk technique; Glovebox; | 86% |
With acetic acid In ethanol for 3h; Heating; | 78% |
2-Picolinic acid
1,2-Bis(2-aminophenoxy)ethane
1,4-bis[o-(pyridine-2-carboxamidophenyl)]-1,4-dioxabutane
Conditions | Yield |
---|---|
Stage #1: 2-Picolinic acid; 1,2-Bis(2-aminophenoxy)ethane In pyridine at 20 - 110℃; Stage #2: With triphenyl phosphite In pyridine Reflux; | 86% |
2,6-Diacetylpyridine
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
In ethanol addn. of the hydrated lanthanide perchlorate in EtOH to a warm soln. of 2,6-diacetylpyridine in EtOH, addn. of the diamine in EtOH with stirringand heating, reflux (4 h); filtration, washing (EtOH), drying (vac.); elem. anal.; | 85.2% |
Conditions | Yield |
---|---|
Stage #1: 1,2-Bis(2-aminophenoxy)ethane With hydrogenchloride; sodium nitrite In water at 5℃; for 0.5h; Cooling with ice; Stage #2: malononitrile With sodium acetate In ethanol; water | 85% |
5-ferrocenyl isophthalic acid chloride
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 12h; | A 82% B 8% |
1,2-Bis(2-aminophenoxy)ethane
2,2′-(ethane-1,2-diildiamine)bisbenzaldehyde
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol Heating; | 80% |
Conditions | Yield |
---|---|
Stage #1: 1,2-Bis(2-aminophenoxy)ethane With hydrogenchloride In water at 20℃; for 2h; Stage #2: With sodium nitrite In water at 0 - 5℃; for 1.83333h; Stage #3: C21H22N2O3 Further stages; | 78.3% |
Conditions | Yield |
---|---|
In toluene; acetonitrile at 60℃; for 3h; | 75% |
1,2-Bis(2-aminophenoxy)ethane
chloroacetyl chloride
1,2-bis(o-chloroacetamidophenoxy)ethane
Conditions | Yield |
---|---|
With sodium carbonate In dichloromethane; water for 1h; | 74% |
(E,E)-monochloroglyoxime
1,2-Bis(2-aminophenoxy)ethane
N,N'-[2,2'-{ethane-1,2-di-yl-bis(oxy)bis(2,1-phenylene)}bis(N'-hydroxy)-2-(hydroxyimino)acetamidamide]
Conditions | Yield |
---|---|
With sodium carbonate In ethanol at 60℃; for 12h; | 73.55% |
1,2-Bis(2-aminophenoxy)ethane
Ethyl 2-bromopropionate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 140℃; for 4h; | 71% |
1,2-Bis(2-aminophenoxy)ethane
benzil
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol Heating; | 71% |
quinolin-2-ylmethylbromide
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 36h; Reflux; | 71% |
2,6-Pyridinedicarboxaldehyde
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
In ethanol addn. of the hydrated lanthanide perchlorate in EtOH to a warm soln. of 2,6-diformylpyridine in EtOH, addn. of the diamine in EtOH with stirringand heating, reflux; filtration, concn., pptn. on addn. of Et2O; elem. anal.; | 70.5% |
1,2-Bis(2-aminophenoxy)ethane
1,2-Bis(4-t-butyl-2-chlorosulfonylphenoxy)ethane
4',5''''-Di-t-butyl-5,6,9,10,15,16,19,20-tetrabenzo-8,17-diaza-1,4,11,14-tetraoxa-7,18-dithiacycloicosane-7,7,18,18-tetraoxide
Conditions | Yield |
---|---|
In dichloromethane for 192h; Heating; | 70% |
allyloxyacetyl chloride
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
With TEA In dichloromethane at 20℃; | 70% |
2,6-Pyridinedicarboxaldehyde
1,2-Bis(2-aminophenoxy)ethane
{Mn(C5H3N(CHNC6H4OCH2)2)(NO3)2}
Conditions | Yield |
---|---|
In acetonitrile mixing of CH3CN solns. of the pyridine dialdehyde, the required dianiline, and the metal salt (slight excess); room temp. for 24 h;; slow evapn. under N2; elem. anal.;; | 70% |
pyridine-2-carbaldehyde
1,2-Bis(2-aminophenoxy)ethane
2,2'-(ethane-1,2-diylbis(oxy))bis(N-(pyridine-2-ylmethyl)aniline)
Conditions | Yield |
---|---|
Stage #1: pyridine-2-carbaldehyde; 1,2-Bis(2-aminophenoxy)ethane In methanol for 12h; Reflux; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 6h; | 70% |
Stage #1: pyridine-2-carbaldehyde; 1,2-Bis(2-aminophenoxy)ethane In methanol for 4h; Reflux; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; | 60% |
2-Hydroxy-4-methoxybenzaldehyde
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
In methanol for 2h; Reflux; | 70% |
Conditions | Yield |
---|---|
In toluene; acetonitrile at 60℃; for 3h; | 70% |
2,6-Pyridinedicarboxaldehyde
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
With H2O In acetonitrile mixing of CH3CN solns. of the pyridine dialdehyde, the required dianiline, and the metal salt (slight excess); room temp. for 24 h;; slow evapn. under N2; elem. anal.;; | 67% |
2,6-Pyridinedicarboxaldehyde
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
In ethanol addn. of the hydrated lanthanide perchlorate in EtOH to a warm soln. of 2,6-diformylpyridine in EtOH, addn. of the diamine in EtOH with stirringand heating, reflux; filtration, concn., pptn. on addn. of Et2O; elem. anal.; | 65.5% |
1,2-Bis(2-aminophenoxy)ethane
Conditions | Yield |
---|---|
In methanol; chloroform CHCl3-soln. of N-compd. was layered onto MeOH soln. of HgI2; crystn. for 30 days, elem. anal.; | 65% |
The Benzenamine,2,2'-[1,2-ethanediylbis(oxy)]bis-, with the CAS registry number 52411-34-4, has the systematic name of 2,2'-[ethane-1,2-diylbis(oxy)]dianiline. It is a kind of off-white crystalline solid, and belongs to the following product categories: Aromatics; Chelating Agents & Ligands; Fluorescent Labels & Indicators. And the molecular formula of the chemical is C14H16N2O2.
The characteristics of Benzenamine,2,2'-[1,2-ethanediylbis(oxy)]bis- are as followings: (1)ACD/LogP: 1.73; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.68; (4)ACD/LogD (pH 7.4): 1.73; (5)ACD/BCF (pH 5.5): 10.82; (6)ACD/BCF (pH 7.4): 12.08; (7)ACD/KOC (pH 5.5): 185.43; (8)ACD/KOC (pH 7.4): 207.03; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 24.94 Å2; (13)Index of Refraction: 1.631; (14)Molar Refractivity: 72.28 cm3; (15)Molar Volume: 202.8 cm3; (16)Polarizability: 28.65×10-24cm3; (17)Surface Tension: 52.9 dyne/cm; (18)Density: 1.204 g/cm3; (19)Flash Point: 253.5 °C; (20)Enthalpy of Vaporization: 71.22 kJ/mol; (21)Boiling Point: 452.9 °C at 760 mmHg; (22)Vapour Pressure: 2.16E-08 mmHg at 25°C.
Preparation of Benzenamine,2,2'-[1,2-ethanediylbis(oxy)]bis-: This chemical can be prepared by 1,2-bis-(2-nitro-phenoxy)-ethane. The reaction will need reagent 80% hydrazine hydrate, catalyst 10% Pd/C, and the menstruum ethanol. The reaction time is 2 hours with heating, and the yield is about 94%.
Uses of Benzenamine,2,2'-[1,2-ethanediylbis(oxy)]bis-: It can react with pentanedioyl dichloride to produce 5,6;14,15-dibenzo-1,4-dioxa-7,13-diazacyclopentadeca-8,12-dione. This reaction will need reagent pyridine, and the menstruum benzene. The reaction time is 3 hours with temperature of 75°C, and the yield is about 50%.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O(c1ccccc1N)CCOc2ccccc2N
(2)InChI: InChI=1/C14H16N2O2/c15-11-5-1-3-7-13(11)17-9-10-18-14-8-4-2-6-12(14)16/h1-8H,9-10,15-16H2
(3)InChIKey: PSDFQEVOCCOOET-UHFFFAOYAY
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