3-Methoxy-2-methylaniline Chemical Properties

Melting point:

27-28°C

Boiling point:

243.4±20.0 °C(Predicted)

Density 

1.08

refractive index 

1.5730-1.5770

Flash point:

>110℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Oil

pka

4.03±0.10(Predicted)

color 

Brown to Dark Brown

InChI

InChI=1S/C8H11NO/c1-6-7(9)4-3-5-8(6)10-2/h3-5H,9H2,1-2H3

InChIKey

OPXLVWLFDKRYRB-UHFFFAOYSA-N

SMILES

C1(N)=CC=CC(OC)=C1C

CAS DataBase Reference

19500-02-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

RIDADR 

2810

WGK Germany 

1

HazardClass 

6.1

PackingGroup 

III

HS Code 

2921490090

3-Methoxy-2-methylaniline Usage And Synthesis

Chemical Properties

Brown Oil

Uses

3-Methoxy-2-methylaniline is a aniline derivative used in the preparation of indoles and indazoles with potential neurochemical activity, as well as in the preparation of quinoline based antiviral agents.

Synthesis

The general procedure for the synthesis of 3-methoxy-2-methylaniline from 2-methyl-3-nitroanisole is as follows (reference Example 42): 1. 9.98 g of a suspension of 5% palladium-carbon (wet) in 100 mL of ethanol was added to a solution of 30.7 g (184 mmol) of 2-methyl-3-nitroanisole in 300 mL of ethanol. 2. The reaction mixture was stirred at room temperature and under hydrogen atmosphere for 3 hours. 3. Upon completion of the reaction, the reaction solution was filtered through diatomaceous earth. 4. The filtrate was concentrated under vacuum to give 25.5 g of 3-methoxy-2-methylaniline as a light purple oil (Yield: quantitative). Rf value: 0.38 (hexane: ethyl acetate = 2:1, v/v). Mass spectrum (EI, m/z): 137 (M+). 1H-NMR spectrum (CDCl3, δ ppm): 2.04-2.05 (m, 3H), 3.60 (brs, 2H), 3.80 (s, 3H), 6.33-6.37 (m, 2H), 6.94-7.01 (m, 1H).

References

[1] Patent: EP1679308, 2006, A1. Location in patent: Page/Page column 56
[2] Patent: US2009/12123, 2009, A1. Location in patent: Page/Page column 14-15
[3] Patent: WO2004/103996, 2004, A1. Location in patent: Page 38-39
[4] Patent: WO2006/7700, 2006, A1. Location in patent: Page/Page column 61
[5] Patent: US2006/19905, 2006, A1. Location in patent: Page/Page column 24

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