2-METHOXY-6-METHYLANILINE Chemical Properties

Melting point:

26-29 °C (lit.)

Boiling point:

62 °C/0.15 mmHg (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 (Slightly), Methanol (Sparingly)

pka

4.39±0.10(Predicted)

form 

Solid

color 

Clear Brown Oil to Pale Red to Dark Red

InChI

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

InChIKey

HKOJYPPTIPJZAZ-UHFFFAOYSA-N

SMILES

C1(N)=C(C)C=CC=C1OC

CAS DataBase Reference

50868-73-0

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2922290090

MSDS

• Language:English Provider:SigmaAldrich

2-METHOXY-6-METHYLANILINE Usage And Synthesis

Uses

2-Methoxy-6-methylaniline may be used in the synthesis of 7-methoxy-1H-indazole, an inhibitor of nitric oxide synthase.

Synthesis

General procedure for the synthesis of 2-methoxy-6-methylaniline from 3-methyl-2-nitroanisole: Step A2; a) Preparation of intermediate 3: 1-methoxy-3-methyl-2-nitrobenzene (25 g, 149.7 mmol) was dissolved in ethanol (100 ml). 10% palladium/carbon catalyst (2.5 g) was added and the reaction mixture was subjected to hydrogenation at room temperature for 24 hours. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration. The filtrate was concentrated under reduced pressure to give Intermediate 3 in a yield of 20.02 g (97% yield). The structure of intermediate 3 was confirmed by CI-MS with a molecular ion peak of 138 ([M + H]+).

References

[1] New Journal of Chemistry, 2006, vol. 30, # 2, p. 168 - 176
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 6, p. 3309 - 3320
[3] Organic letters, 2000, vol. 2, # 3, p. 277 - 280
[4] Patent: WO2006/15985, 2006, A1. Location in patent: Page/Page column 54-55
[5] Journal of the Chemical Society, 1926, p. 1425

2-METHOXY-6-METHYLANILINE(50868-73-0)Related Product Information

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• DISPERSE VIOLET 26
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• 2-Methyl-4-methoxybenzenamine
• 2-Methoxy-4-methylaniline, HCl
• N-METHYL-P-ANISIDINE
• 3-METHOXY-N-METHYLANILINE