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5-Methoxy-2-methylaniline

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CAS:50868-72-9
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5-Methoxy-2-methylaniline manufacturers

5-Methoxy-2-methylaniline Basic information
Product Name:5-Methoxy-2-methylaniline
Synonyms:3-AMino-4-Methylanisole[5-Methoxy-2-Methylaniline];LABOTEST-BB LTBB000645;5-Methoxy-2-Methylaniline, 97% 1GR;5-Methoxy-2-Methylaniline, 97% 5GR;6-METHYL-M-ANISIDINE;3-Amino-4-methylanisole;3-Methoxy-6-methylaniline;Benzenamine, 5-methoxy-2-methyl-
CAS:50868-72-9
MF:C8H11NO
MW:137.18
EINECS:256-816-4
Product Categories:Amines;Building Blocks;C8;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Anilines, Aromatic Amines and Nitro Compounds
Mol File:50868-72-9.mol
5-Methoxy-2-methylaniline Structure
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)
Fp >230 °F
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility Chloroform (Sparingly), Methanol (Slightly)
form Powder
pka4.03±0.10(Predicted)
color Off-white to pale grey to yellow
Water Solubility Slightly soluble in water.
InChIInChI=1S/C8H11NO/c1-6-3-4-7(10-2)5-8(6)9/h3-5H,9H2,1-2H3
InChIKeyRPJXLEZOFUNGNZ-UHFFFAOYSA-N
SMILESC1(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 Information
ProviderLanguage
5-Methoxy-2-methylaniline English
SigmaAldrich English
5-Methoxy-2-methylaniline Usage And Synthesis
Chemical PropertiesWhite to gray to tan crystalline powder
Uses5-Methoxy-2-methylaniline was used in the preparation of N-(5-methoxy-2-methylphenyl)acetamide.
Uses5-Methoxy-2-methylaniline was used in the preparation of N-(5-methoxy-2-methylphenyl)acetamide.
Synthesis
4-Methyl-3-nitroanisole

17484-36-5

5-Methoxy-2-methylaniline

50868-72-9

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