9,10-DIAMINOPHENANTHRENE Chemical Properties

Melting point:

164-166 °C (lit.)

Boiling point:

457.6±25.0 °C(Predicted)

Density 

1.283±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

5.15±0.30(Predicted)

form 

solid

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C14H12N2/c15-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(13)16/h1-8H,15-16H2

InChIKey

VPRFQZSTJXHBHL-UHFFFAOYSA-N

SMILES

C1=C2C(C3C(C(N)=C2N)=CC=CC=3)=CC=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2921599090

MSDS

• Language:English Provider:SigmaAldrich

9,10-DIAMINOPHENANTHRENE Usage And Synthesis

Synthesis

The general procedure for the synthesis of 9,10-diaminophenanthrene from 9,10-dibromophenanthrene was as follows: 1-3,200 mmol of 9,10-dibromophenanthrene was added to the reaction vessel; 300 mmol of ammonia, 600 mmol of potassium tert-butoxide, and 32 mol of Pd2(dba)3 were subsequently added, and dissolved by stirring with deoxidized toluene with ultrasonic assistance. The air in the reaction system was displaced three times and the ligand tri-tert-butylphosphine (4%, 8 mmol) was added. After displacing the air again three times, the reaction mixture was refluxed for 6 hours. After completion of the reaction, it was cooled to room temperature and sufficient dichloromethane was added to completely dissolve the product. The product was filtered through a funnel containing a small amount of silica gel to remove the catalyst and salt. The filtrate was concentrated to a viscous state and finally purified by column chromatographic separation to afford the target product 9,10-diaminophenanthrene in 170 mmol yield.

References

[1] Patent: CN108516961, 2018, A. Location in patent: Paragraph 0099; 0101

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