2-Bromo-7-hydroxynaphthalene Chemical Properties

Melting point:

133-138 °C

Boiling point:

353.8±15.0 °C(Predicted)

Density 

1.614±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

9.17±0.40(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C10H7BrO/c11-9-3-1-7-2-4-10(12)6-8(7)5-9/h1-6,12H

InChIKey

VWSBGGRCEQOTNU-UHFFFAOYSA-N

SMILES

C1=C2C(C=CC(Br)=C2)=CC=C1O

CAS DataBase Reference

116230-30-9

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29081990

2-Bromo-7-hydroxynaphthalene Usage And Synthesis

Uses

2-Bromo-7-hydroxynaphthalene is used as an intermediate in organic synthesis and pharmaceuticals.

Chemical Properties

White powder

Synthesis

The general procedure for the synthesis of 7-bromo-2-naphthol from 2,7-dihydroxynaphthalene was as follows: 1. Preparation of 2-bromo-7-methoxynaphthalene: Triphenylphosphine (89.7 g, 0.342 mol) and acetonitrile (350 mL) were added to a 1 L flask under nitrogen protection and the mixture was cooled to 10 °C. Bromine (17.6 mL, 0.342 mol) was added slowly and dropwise over 10 min. After removing the cooling bath, 2,7-dihydroxynaphthalene (50.0 g, 0.312 mol) was added and rinsed with 350 mL of acetonitrile. The resulting yellow-brown mixture was heated to reflux for 3 hours. Subsequently, the acetonitrile was removed by distillation under reduced pressure, taking about 2 hours to give an off-white solid. 2. Preparation of 7-bromo-2-naphthol: The above solid was heated to 280°C within 30 minutes to form a black liquid. The liquid was continued to be heated to 310°C within 20 minutes and maintained at this temperature for 15 minutes until gas release ceased. After the black mixture was cooled to room temperature, 34.5 g of the intermediate title compound was obtained by chromatographic separation as an off-white solid with HPLC purity of 87% (43% yield).

References

[1] Journal of the American Chemical Society, 2008, vol. 130, # 13, p. 4541 - 4552
[2] Dyes and Pigments, 2014, vol. 107, p. 174 - 181
[3] Patent: WO2015/121785, 2015, A1. Location in patent: Page/Page column 32; 33
[4] Helvetica Chimica Acta, 1999, vol. 82, # 7, p. 981 - 1004
[5] Chemical Communications, 2012, vol. 48, # 5, p. 750 - 752

2-Bromo-7-hydroxynaphthalene(116230-30-9)Related Product Information

• 1-Bromonaphthalene
• 2-Hydroxypyridine
• Hydroxyapatite
• Methylparaben
• 4-Methoxyphenol
• Glycolic acid
• 2-Naphthol
• 1-Naphthol
• 4-Hydroxybenzoic acid
• 4-Hydroxybenzaldehyde
• 2-Bromo-6-hydroxynaphthalene,6-BROMO2-HYDROXYNAPHTHALENE
• Hydroxy silicone oil
• Camptothecin Series--10-hydroxycamptothecin
• Bromine
• 1-BROMO-2-HYDROXYNAPHTHALENE
• 1,6-DIBROMO-2-HYDROXYNAPHTHALENE-3-CARBOXYLIC ACID
• 2-Bromo-7-hydroxynaphthalene
• 3-Bromo-2-naphthol