1-(Bromomethyl)naphthalene Chemical Properties

Melting point:

52-55°C

Boiling point:

213°C/100mmHg

Density 

1.44

refractive index 

1.6600

storage temp. 

Inert atmosphere,2-8°C

form 

Powder

color 

Off-white

Water Solubility 

Slightly soluble in water.

λmax

292nm(Cyclohexane)(lit.)

CAS DataBase Reference

3163-27-7(CAS DataBase Reference)

NIST Chemistry Reference

1-(Bromomethyl)naphthalene(3163-27-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

RIDADR 

3261

HazardClass 

8

PackingGroup 

II

HS Code 

29036990

1-(Bromomethyl)naphthalene Usage And Synthesis

Chemical Properties

Off-white powder

Uses

It is employed as a intermediate for organic synthesis and pharmaceutical.

Synthesis

The general procedure for the synthesis of 1-bromomethylnaphthalene from 1-naphthalenemethanol: Ethyl α,α-diacetoacetate (0.41 mmol, 1.2 eq.), 1-naphthalenemethanol (0.34 mmol, 1.0 eq.), and triphenylphosphine (0.68 mmol, 2.0 eq.) were added to 3 mL of dichloroethane (DCE) at room temperature and the reaction took place in air. The progress of the reaction was monitored by thin layer chromatography (TLC) during the reaction. Upon completion of the reaction, the reaction was quenched by the addition of 3 mL of water, followed by extraction with ethyl acetate (3 x 3 mL). The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography, and the eluent was petroleum ether or a mixed solvent of petroleum ether and ethyl acetate, and the target product 1-bromomethyl naphthalene was finally obtained.

References

[1] Synthetic Communications, 2010, vol. 40, # 11, p. 1646 - 1649
[2] Organic Letters, 2003, vol. 5, # 8, p. 1167 - 1169
[3] Tetrahedron Letters, 2014, vol. 55, # 1, p. 90 - 93
[4] Canadian Journal of Chemistry, 1981, vol. 59, p. 2629 - 2641
[5] Tetrahedron, 2003, vol. 59, # 52, p. 10453 - 10463

1-(Bromomethyl)naphthalene(3163-27-7)Related Product Information

• Methylnaphthalene
• Bromotrimethylsilane
• 1-Bromonaphthalene
• 2-Acetonaphthone
• 2,6-DIMETHYLNAPHTHALENE
• Naphthalene
• 2-(Bromomethyl)naphthalene
• Methyl bromide
• 1-BROMO-4-(BROMOMETHYL)NAPHTHALENE
• 1,4-BIS(BROMOMETHYL)NAPHTHALENE
• 1,8-BIS(BROMOMETHYL)NAPHTHALENE
• 4-(BROMOMETHYL)NAPHTHALENE-1-CARBONITRILE
• 1-(BROMOMETHYL)-4-NITRONAPHTHALENE
• 9,10-Bis(bromomethyl)anthracene
• ALPHA-BROMO-1-NAPHTHALENEACETIC ACID ETHYL ESTER
• 3-(BROMOMETHYL)PYRENE
• 4-(BROMOMETHYL)NAPHTHALENE-1-CARBOXYLIC ACID
• 1-Bromomethyl-7-fluoro-naphthalene