2,2'-ETHYLENEDIANILINE Chemical Properties

Melting point:

72-77 °C

Boiling point:

342.14°C (rough estimate)

Density 

1.0799 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

4.49±0.10(Predicted)

color 

Pale Yellow to Beige

InChI

InChI=1S/C14H16N2/c15-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)16/h1-8H,9-10,15-16H2

InChIKey

ZYHQGITXIJDDKC-UHFFFAOYSA-N

SMILES

C(C1=CC=CC=C1N)CC1=CC=CC=C1N

LogP

1.929 (est)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36/37

MSDS

• Language:English Provider:ACROS

2,2'-ETHYLENEDIANILINE Usage And Synthesis

Chemical Properties

BROWN POWDER

Uses

2,2''-Ethylenedianiline is used as a reagent to synthesize Oxcarbazepine (O869250), a broad-specturm, second-generation anticonvulsant drug that is used to treat partial and complex partial seizures in children and adults. 2,2''-Ethylenedianiline is also used as a reagent to prepare a series of triterpines (e.g. Lupeol [L474850]), compounds that have chemopreventative activity.

Synthesis

A. Preparation of loaded nickel catalysts In a 25 mL round-bottomed flask, 4.75 g of nickel chloride hexahydrate was dissolved in 15 mL of deionized water, 20 g of neutral alumina was added, sonicated and dried overnight. Weigh 0.3 g of sodium borohydride and prepare 800 mL of 0.01 mol/L solution. Add 5 g of precursor to a 1 L flask, add mechanical stirring, and slowly add aqueous sodium borohydride solution, filter the product after the reaction is complete and dry to obtain the desired catalyst. B. Synthesis of 2,2'-(ethane-1,2-diyl)diphenylamine In a 10 mL round bottom flask, 300 mg of 2-nitrobenzyl chloride, 300 mg of catalyst, 2 mL of deionized water and 2 mL of 60% hydrazine hydrate were slowly added dropwise with magnetic stirring until complete incorporation and stirred continuously for 20 min at room temperature to obtain the reaction mixture. The reaction mixture was extracted with ethyl acetate and analyzed by GC-MS to give about 51% yield of the target product. The catalyst was washed three times each with water and ethanol and dried for reuse.

References

[1] Patent: CN107417542, 2017, A. Location in patent: Paragraph 0014-0015; 0016-0017

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