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2,2'-(Ethylenedioxy)dianiline
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Name

2,2'-(Ethylenedioxy)dianiline

 EINECS 1312995-182-4
CAS No. 52411-34-4 Density 1.204 g/cm3
PSA 70.50000 LogP 3.47120
Solubility N/A Melting Point 131-132 °C
Formula C14H16N2O2 Boiling Point 452.9 °C at 760 mmHg
Molecular Weight 244.293 Flash Point 253.5 °C
Transport Information N/A Appearance off-white crystalline solid
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 52411-34-4 (2-[2-(2-Aminophenoxy)ethoxy]phenylamine) Hazard Symbols N/A
Synonyms

Aniline,2,2'-(ethylenedioxy)di- (6CI);1,2,7,8-Dibenzo-1,8-diamino-3,6-dioxaoctane;1,2-Bis(o-aminophenoxy)ethane;1,2-Bis[2-aminophenoxy]ethane;1,2-Di(o-aminophenoxy)ethane;2,2'-[1,2-Ethanediylbis(oxy)]bis[benzenamine];

Article Data 27

2,2'-(Ethylenedioxy)dianiline Synthetic route

51661-19-9

1,2-bis(2-nitrophenoxy)ethane

52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
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%
67499-49-4

1,2-bis-(2-acetylamino-phenoxy)-ethane

52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
bei der Destillation;
ethylene glycol-bis-<2-nitro-phenyl ether >

ethylene glycol-bis-<2-nitro-phenyl ether >

52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
With hydrogenchloride; tin
824-39-5

sodium o-nitrophenate

52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
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
88-75-5

2-hydroxynitrobenzene

dichloropentamethylenetetramine

dichloropentamethylenetetramine

52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaOH / ethanol
2: dimethylformamide / 2 h / Heating
3: 10percent Pd/C / ethanol
View Scheme
88-75-5

2-hydroxynitrobenzene

52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
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
102236-25-9

1-(2-chloroethoxy)-2-nitrobenzene

52411-34-4

1,2-Bis(2-aminophenoxy)ethane

Conditions
ConditionsYield
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

1,2-bis[2-(N-acetoacetamide)phenoxy]ethane

100-52-7

benzaldehyde

57-13-6

urea

A

52411-34-4

1,2-Bis(2-aminophenoxy)ethane

B

5-Ethoxy-6-methyl-4-(phenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With hydrogenchloride In ethanol Reflux;
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

122-51-0

orthoformic acid triethyl ester

1,2-bis[2-(1H-tetrazol-1-yl)phenoxy]ethane

Conditions
ConditionsYield
With sodium azide; acetic acid at 90℃;99%
52411-34-4

1,2-Bis(2-aminophenoxy)ethane

26576-46-5

5-(acetoacetamido)-2-benzimidazolinone

C.I. pigment yellow 180

Conditions
ConditionsYield
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%

2,2'-(Ethylenedioxy)dianiline Specification

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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