4,6-Diaminoresorcinol dihydrochloride Chemical Properties

Melting point:

254 °C (dec.)(lit.)

storage temp. 

2-8°C

form 

Crystalline Solid

color 

Gray-brown

Water Solubility 

almost transparency

InChI

InChI=1S/C6H8N2O2.2ClH/c7-3-1-4(8)6(10)2-5(3)9;;/h1-2,9-10H,7-8H2;2*1H

InChIKey

KUMOYHHELWKOCB-UHFFFAOYSA-N

SMILES

C1(N)=CC(=C(O)C=C1O)N.Cl.Cl

CAS DataBase Reference

16523-31-2(CAS DataBase Reference)

EPA Substance Registry System

1,3-Benzenediol, 4,6-diamino-, dihydrochloride (16523-31-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-24/25

WGK Germany 

3

HS Code 

29222990

MSDS

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

4,6-Diaminoresorcinol dihydrochloride Usage And Synthesis

Chemical Properties

grey-brown crystalline solid

Uses

4,6-Diaminoresorcinol dihydrochloride may be used as a precursor in the synthesis of:

• poly(p-phenylene benzobisoxazole) (PBO)
• poly(2,6-naphthalenebenzobisoxazole) (Naph-2,6-PBO)
• poly(1,5-naphthalenebenzobisoxazole) (Naph-1,5-PBO)

Synthesis

The general procedure for the synthesis of 4,6-diaminoresorcinol dihydrochloride from resorcinol was as follows: the reaction was carried out by the one-pot method under the molar ratio of phosphorus pentoxide/methanesulfonic acid/hydroxylamine hydrochloride/acetic acid/resorcinol of 0:4:2:2:1. The specific operation was as follows: first, resorcinol (5.50 g) and acetic acid (6.00 g) were added to a 100 mL three-necked flask, followed by the addition of methanesulfonic acid (13 mL, 0.2 mol), and the reaction system was warmed up to 100 °C after stirring until complete dissolution. Next, hydroxylamine hydrochloride (7.00 g) was slowly added and the reaction was continued at this temperature for 4 hours. Upon completion of the reaction, 6 mol/L hydrochloric acid (40 mL) was added to the system and stirring was continued. The reaction mixture was cooled at 100 °C for 2 h, during which time crystals precipitated. The crystals were collected by filtration, washed sequentially with hydrochloric acid and ethanol, and finally dried under vacuum to afford the target product 4,6-diaminoresorcinol dihydrochloride in 5.0% yield.

References

[1] Patent: CN108191678, 2018, A. Location in patent: Paragraph 0016-0021
[2] Patent: CN103724216, 2016, B
[3] Patent: CN104098590, 2016, B

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