1,2-Diphenylethylenediamine Chemical Properties

Melting point:

123-125 °C(lit.)

Boiling point:

305-307 °C744 mm Hg(lit.)

Density 

0.97 g/mL at 25 °C(lit.)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

9.78±0.10(Predicted)

color 

White to Yellow to Orange

CAS DataBase Reference

16635-95-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-36-51/53

Safety Statements 

26-36/37-61

RIDADR 

2735

WGK Germany 

2

RTECS 

WJ4926500

HS Code 

2921.59.8090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1,2-Diphenylethylenediamine Usage And Synthesis

Uses

1,2-Diphenylethylenediamine (DPE) has been found to react in a neutral medium with catecholamines and other catechol compounds in the presence of hexacyanoferrate(III) to give a compound that fluoresces intensely. The reaction is accelerated by amino acids such as glycine. Nohta et al. described a sensitive spectrofluorimetric method for determining catecholamines with 1,2diphenylethylenediamine. The method is based on the reaction of catechol compounds in a neutral medium with 1,2-diphenylethylenediamine in the presence of hexacyanoferrate(II1) and glycine at ambient temperature. The fluorescence shows excitation and emission maxima around 345 and 480 nm, respectively. The method is simple, selective for catechol compounds, and very sensitive. Catecholamines can be determined at concentrations as low as 15-20 pmol ml^-1[1].

Synthesis

To a 500-ml four-necked flask fitted with a condenser was added 1,2-diphenylethanedione dioxime (48 g, 0.20 mol) and 260 ml of methanol, stirring to dissolve it all, then add 2 g of activated carbon (120 mesh), 0.5 g of Raney nickel, raise the temperature to 60 ?? C, slowly add 80% hydrazine hydrate (28.75 g, 0.46 mol) dropwise, keep the reaction temperature Degree of 58 ?? -62 ??, the reaction process has nitrogen release, drop acceleration control in the nitrogen release rate is not easy too fast for good, liquid chromatography. Too fast for good, liquid chromatography to track the reaction process, when the raw material 1,2-diphenylethanedione dioxime disappeared after the end of the reaction, cooling the mixture, filtration of Raney nickel and activated carbon, covered with a small amount of water to save for the set of use, filtrate distillation Recovery of methanol, the residue added 200 ml of petroleum ether heated to dissolve all of them, cooled for 24 hours and filtered to get the product (??)-1,2-diphenylethylenediamine 41.55 g, yield 98%, chemical purity 99.57%.

References

[1] H. Nohta, Y. Ohkura, A. Mitsui. “Spectrofluorimetric determination of catecholamines with 1,2-diphenylethylenediamine.” Analytica Chimica Acta 165 1 (1984): 171–176.

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