| Identification | Back Directory | [Name]
2-METHOXY-6-METHYLANILINE | [CAS]
50868-73-0 | [Synonyms]
6-METHYL-O-ANISIDINE
6-Methoxy-o-toluidine
2-Amino-3-methylanisole
2-Methyl-6-methoxyaniline
6-Methoxy-2-methylaniline
2-METHOXY-6-METHYLANILINE
2-Methoxy-6-methylbenzenamine
2-Methoxy-6-methylaniline 98%
2-Methoxy-6-methyl-phenylamine
BenzenaMine, 2-Methoxy-6-Methyl-
2-Amino-1-methoxy-3-methylbenzene
2-Methoxy-6-methylaniline,6-Methyl-o-anisidine
6-Methoxy-o-toluidine
2-Amino-1-methoxy-3-methylbenzene | [Molecular Formula]
C8H11NO | [MDL Number]
MFCD00075455 | [MOL File]
50868-73-0.mol | [Molecular Weight]
137.18 |
| Chemical Properties | Back Directory | [Melting point ]
26-29 °C(lit.)
| [Boiling point ]
62 °C0.15 mm Hg(lit.)
| [density ]
1.0630 (rough estimate) | [refractive index ]
1.5647 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Chloroform (Slightly), Methanol (Sparingly) | [form ]
Solid | [pka]
4.39±0.10(Predicted) | [color ]
Clear Brown Oil to Pale Red to Dark Red Low Melting | [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 |
| Hazard Information | Back Directory | [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 |
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