1-(Benzyloxy)-2-methyl-3-nitrobenzene Chemical Properties

Melting point:

60-63 °C (lit.)

Boiling point:

170-176 °C(Press: 0.8 Torr)

Density 

1.202±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

Powder

color 

Yellow to pale brown

CAS DataBase Reference

20876-37-3(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29093090

MSDS

• Language:English Provider:SigmaAldrich

1-(Benzyloxy)-2-methyl-3-nitrobenzene Usage And Synthesis

General Description

1-Benzyloxy-2-methyl-3-nitrobenzene may be used in the preparation of 1-[2-[2-(benzyloxy)-6-nitrophenyl]vinyl]pyrrolidine and 4-(benzyloxy)-1H-indole.

Synthesis

General procedure: 41.5 g (300 mmol) of potassium carbonate and 200 mL of N,N-dimethylformamide were added to a reaction vial containing 30.6 g (200 mmol) of 2-methyl-3-nitrophenol. Under argon protection, 23.8 mL (200 mmol) of benzyl bromide was slowly added dropwise to the reaction system and the reaction was stirred at room temperature for 3 hours. Upon completion of the reaction, the reaction solution was poured into 1000 mL of water, extracted with 800 mL of toluene and the extraction was repeated once (500 mL of toluene). The organic phases were combined, washed sequentially with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure to give 49.3 g of yellow powdered 1-benzyloxy-2-methyl-3-nitrobenzene in quantitative yield. rf value: 0.48 (unfolding reagent: n-hexane/ethyl acetate=4:1, v/v). Mass spectrum (CI, m/z): 244 [M+1]+. 1H-NMR (CDCl3, δ ppm): 2.42 (s, 3H), 5.13 (s, 2H), 7.08-7.11 (m, 1H), 7.21-7.27 (m, 1H), 7.32-7.44 (m, 6H).

References

[1] Patent: US2009/12123, 2009, A1. Location in patent: Page/Page column 9-10
[2] Patent: WO2005/117909, 2005, A2. Location in patent: Page/Page column 119
[3] Journal of the Chemical Society, 1948, p. 1605,1608
[4] Heterocycles, 1981, vol. 16, # 7, p. 1119 - 1124
[5] Patent: EP1870099, 2007, A1. Location in patent: Page/Page column 14

1-(Benzyloxy)-2-methyl-3-nitrobenzene(20876-37-3)Related Product Information

• Methylparaben
• Phenethyl alcohol
• Ethoxymethylenemalononitrile
• 2-Methyl-3-nitrophenol
• Benzyl ether
• 4-Methoxybenzylchloride
• 4-Nitrobenzyl alcohol
• Methyl acrylate
• Methyltrimethoxysilane
• Triton X-100
• 2-CHLOROTHIOPHENOL
• Bensulfuron methyl
• Chlorodimethylphenylsilane
• Methyl acetate
• Dimethyldimethoxysilane
• Methyltriethoxysilane
• 2-Methyl-3-nitro-benzeneacetic acid
• Thiophanate-methyl