1,6-Dibromo-2-naphthol Chemical Properties

Melting point:

105-107 °C(lit.)

Boiling point:

368.5±22.0 °C(Predicted)

Density 

1.7523 (rough estimate)

refractive index 

1.5560 (estimate)

storage temp. 

Sealed in dry,Room Temperature

pka

6.94±0.50(Predicted)

form 

Powder

color 

Pink to purple or light brown

CAS DataBase Reference

16239-18-2(CAS DataBase Reference)

EPA Substance Registry System

1,6-Dibromo-2-naphthol (16239-18-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

WGK Germany 

3

RTECS 

QL3500000

HS Code 

29081990

MSDS

• Language:English Provider:1,6-Dibromo-2-naphthol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

1,6-Dibromo-2-naphthol Usage And Synthesis

Chemical Properties

Pink to purple or light brown powder

Synthesis

General procedure for the synthesis of 1,6-dibromo-2-naphthol from 6-bromo-2-naphthol: 6-bromo-2-naphthol (500 mg, 2.242 mmol, 1.0 eq.) was reacted with N-bromosuccinimide (NBS, 558.7 mg, 3.319 mmol, 1.4 eq.) in acetone (4.4 mL) and 1 N HCl (22 μL) in a mixed solution of acetone (4.4 mL) and 1 N HCl (22 μL) at room temperature with stirring for 15 min. Upon completion of the reaction, ethyl acetate was added for extraction and the organic phase was washed three times with 1 N HCl to remove unreacted NBS and by-products. Subsequently, the organic phase was dried with anhydrous magnesium sulfate, the desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure on a rotary evaporator to afford the target product 1,6-dibromo-2-naphthol in quantitative yield (677 mg). The product characterization data were as follows: molecular formula C10H6Br2O; molecular weight 300/302/304; 1H NMR (CDCl3, δ): 7.90 (d, J = 1.8 Hz, 1H), 7.87 (d, J = 8.8 Hz, 1H), 7.61 (d, J = 8.8 Hz, 1H), 7.59 (dd, J = 2.1 Hz, J = 9.1 Hz, 1H), 7.24 (d, J = 8.8 Hz, 1H); 13C NMR (CDCl3, δ): 177.5, 151.0, 131.0, 130.6, 130.1, 128.4, 128.3, 127.2, 118.0, 106.1; IR (cm-1): 3443, 1688, 1617, 1586 1382, 1209, 1183, 1130.

References

[1] Patent: US2010/204234, 2010, A1. Location in patent: Page/Page column 15
[2] RSC Advances, 2018, vol. 8, # 32, p. 17806 - 17812
[3] Synthetic Communications, 1996, vol. 26, # 13, p. 2597 - 2601
[4] Chemical Communications, 2018, vol. 54, # 39, p. 4935 - 4938

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