5-Methoxy-2-methylaniline Chemical Properties

Melting point:

43-46 °C (lit.)

Boiling point:

253°C(lit.)

Density 

1.0630 (rough estimate)

refractive index 

1.5647 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Powder

pka

4.03±0.10(Predicted)

color 

Off-white to pale grey to yellow

Water Solubility 

Slightly soluble in water.

InChI

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

InChIKey

RPJXLEZOFUNGNZ-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

6.1

HS Code 

29222990

MSDS

• Language:English Provider:5-Methoxy-2-methylaniline
• Language:English Provider:SigmaAldrich

5-Methoxy-2-methylaniline Usage And Synthesis

Chemical Properties

White to gray to tan crystalline powder

Uses

5-Methoxy-2-methylaniline was used in the preparation of N-(5-methoxy-2-methylphenyl)acetamide.

Uses

5-Methoxy-2-methylaniline was used in the preparation of N-(5-methoxy-2-methylphenyl)acetamide.

Synthesis

Under nitrogen atmosphere, 4-methoxy-1-methyl-3-nitrobenzene (18.0 g, 108 mmol) was dissolved in 160 mL of 1,2-dimethoxyethane (DME), followed by the addition of 10% Pd/C catalyst (0.9 g). Hydrazine hydrate (16.17 g, 323 mmol) was slowly added dropwise to the above solution. The reaction mixture was heated to reflux and stirred continuously for 4 hours. After that, 3 mL of hydrazine hydrate was added additionally and stirring was continued under reflux conditions for 2 days. Upon completion of the reaction, the mixture was cooled to room temperature and filtered through a diatomaceous earth pad to remove the catalyst. The filtrate was concentrated under reduced pressure to remove the solvent to give the crude product 5-methoxy-2-methylaniline as a yellow oil. After further vacuum drying, the product solidified to a pale yellow solid in a yield of 14.8 g (100% yield). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 6.94 (d, J = 7.53 Hz, 1H), 6.28 (d, J = 7.53 Hz, 1H), 6.26 (s, 1H), 3.78 (s, 3H), 3.5 (br, 1H), 2.10 (s, 3H), 1.6 (br, 1H).

References

[1] Patent: WO2009/117097, 2009, A1. Location in patent: Page/Page column 70-71
[2] Tetrahedron, 2018, vol. 74, # 12, p. 1294 - 1306
[3] Justus Liebigs Annalen der Chemie, 1882, vol. 215, p. 83
[4] Journal of the Chemical Society, 1929, p. 870
[5] Journal of the Chemical Society, 1925, vol. 127, p. 995

5-Methoxy-2-methylaniline(50868-72-9)Related Product Information

• N-Methylaniline
• 2-BROMO-5-METHOXYANILINE
• 4-(Trifluoromethoxy)aniline
• METHYL THIOPHENE-2-CARBOXYLATE
• Toluidine Blue O
• Kresoxim-methyl
• Methylparaben
• p-Anisidine
• o-Anisidine
• o-Toluidine
• Bensulfuron methyl
• N,N-Dimethyl-1,4-phenylenediamine
• 3,3',5,5'-Tetramethylbenzidine dihydrochloride
• Methyl acrylate
• N,N-Dimethylaniline
• Thiophanate-methyl
• Methyl
• anisidine