1-BROMO-2-METHOXYNAPHTHALENE Chemical Properties

Melting point:

80-83 °C

Boiling point:

190-192 °C(Press: 22 Torr)

Density 

1.447±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Light yellow

Water Solubility 

Slightly soluble in water.

BRN 

2045600

InChI

InChI=1S/C11H9BrO/c1-13-10-7-6-8-4-2-3-5-9(8)11(10)12/h2-7H,1H3

InChIKey

XNIGURFWNPLWJM-UHFFFAOYSA-N

SMILES

C1(Br)=C2C(C=CC=C2)=CC=C1OC

CAS DataBase Reference

3401-47-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29093090

MSDS

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

1-BROMO-2-METHOXYNAPHTHALENE Usage And Synthesis

Chemical Properties

solid

Uses

1-Bromo-2-methoxy-naphthalene is a useful synthetic intermediate. It is used as a reagent to synthesize a catalyst for highly enantioselective aziridination of styrene derivatives. It can also be used to prepare biaryls or biheterocycles by palladium-catalyzed Ullmann coupling.

Synthesis

In a 500 mL round-bottomed three-necked flask, 1-bromo-2-naphthol (30.0 g, 134.5 mmol), potassium hydroxide (KOH, 11.3 g, 201.7 mmol) and 300 mL of dimethylsulfoxide (DMSO) were added, and stirred under nitrogen protection for 10 min. Subsequently, the reaction system was cooled in an ice-water bath and iodomethane (28.6 g, 201.7 mmol) was added dropwise slowly. After the dropwise addition, stirring was continued at room temperature under nitrogen atmosphere for 12 h. The reaction was then warmed up to 50 °C for 1 h. The reaction was then completed by cooling to 50 °C for 10 min. After completion of the reaction, it was cooled to room temperature. The reaction mixture was poured into 500 mL of water and extracted with ether. The organic phase was washed three times with distilled water and dried over anhydrous magnesium sulfate (MgSO4). After the solvent was evaporated under reduced pressure, it was purified by silica gel column chromatography (eluent: n-hexane) to afford 1-bromo-2-methoxynaphthalene 22.0 g (yield 69.0%) as a white solid.

References

[1] Patent: KR2016/17530, 2016, A. Location in patent: Paragraph 0238; 0241; 0245; 0246
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 24, p. 4800 - 4818
[3] Journal of Organic Chemistry, 2000, vol. 65, # 5, p. 1511 - 1515
[4] Patent: JP5656843, 2015, B2. Location in patent: Paragraph 0092; 0093
[5] Journal of the Chemical Society, 1900, vol. 77, p. 37

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