1-BROMO-2-METHYLNAPHTHALENE Chemical Properties

Melting point:

127-128℃

Boiling point:

162-164 °C/12 mmHg (lit.)

Density 

1.419 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.651(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

liquid

Appearance

Colorless to light yellow Liquid

Water Solubility 

Sparingly Soluble in water. (1.9E-3 g/L) (25°C).

CAS DataBase Reference

6627-78-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

MSDS

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

1-BROMO-2-METHYLNAPHTHALENE Usage And Synthesis

Synthesis

General procedure for the synthesis of 1-bromo-4-methylnaphthalene from 1-methylnaphthalene: A mixture of 1-methylnaphthalene (14.28 g, 200 mmol) and N-bromosuccinimide (NBS, 39.16 g, 220 mmol) in acetonitrile (MeCN, 300 mL) was reacted with stirring at 30-40 °C until the reaction was shown by thin layer chromatography (TLC) analysis to be was complete (typically 12 hours). Upon completion of the reaction, the mixture was cooled to room temperature, poured into water (600 mL) and extracted with dichloromethane (CH2Cl2, 500 mL x 3). The organic phases were combined and washed sequentially with 5% sodium thiosulfate (Na2S2O3) aqueous solution (200 mL), saturated sodium carbonate (Na2CO3) aqueous solution (100 mL × 3) and 5% brine (200 mL). The organic layer was dried over anhydrous sodium sulfate (Na2SO4) and the solvent was removed by rotary evaporation to obtain the crude product. Purification by column chromatography afforded the target product 1-bromo-4-methylnaphthalene (15) as a colorless oil in a yield of 42.01 g (98% yield).1H-NMR (DMSO-d6, 400 MHz) δ: 8.14-8.16 (m, 1H), 8.07-8.09 (m, 1H), 7.76 (d, J = 7.6 Hz, 1H), 7.66 -7.70 (m, 2H), 7.30 (d, J = 7.6 Hz, 1H), 2.63 (s, 3H).

References

[1] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 2093 - 2094
[2] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 439 - 443
[3] Molecules, 2018, vol. 23, # 2,
[4] Journal of Organic Chemistry, 2018, vol. 83, # 2, p. 930 - 938
[5] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204

1-BROMO-2-METHYLNAPHTHALENE(6627-78-7)Related Product Information

• 3-Bromobenzanthrone
• 4-Bromo-1,8-naphthalic anhydride
• 1-BROMO-4-(BROMOMETHYL)NAPHTHALENE
• 5-Bromoacenaphthene
• 4-Bromo-1,8-naphthalic anhydride
• 10,10'-Dibromo-9,9'-bianthryl
• 1-BROMO-2-METHYLNAPHTHALENE
• 3,9-Dibromobenzanthrone
• Vat Orange 3
• t-Butyl 4-bromo-1-naphthalenecarboxylate
• 3-BROMOFLUORANTHENE
• ANTHRACENE, 9-BROMO-10-(1-NAPHTHALENYL)-
• 9-Bromo-10-(2-naphthyl)anthracene
• 4-BROMO-1-NAPHTALENECARBOXYLIC ACID
• Methyl 4-bromo-1-naphthoate
• 1-BROMO-2-METHYLNAPHTHALENE
• 1-Bromonaphthalene
• 2-Methylnaphthalene