2-Methyl-3-amino-4-acetylanisole

2-Methyl-3-amino-4-acetylanisole Property

Melting point:

107 °C

Boiling point:

336.0±37.0 °C(Predicted)

Density 

1.096±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

1.74±0.10(Predicted)

color 

White to Yellow to Orange

InChI

InChI=1S/C10H13NO2/c1-6-9(13-3)5-4-8(7(2)12)10(6)11/h4-5H,11H2,1-3H3

InChIKey

VXBGCEDOGYNWHE-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=C(OC)C(C)=C1N)C

Safety

HS Code 

2922500090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

2-Methyl-3-amino-4-acetylanisole Chemical Properties,Usage,Production

Synthesis

To a solution of 2-methyl-3-methoxyaniline (5.0 g, 36.5 mmol) in p-xylene (80 mL) was cooled to 0 °C, and a dichloromethane solution (36.5 mL) of 1 M BCl3 was slowly added. The reaction mixture was stirred at 0 °C for 30 min under nitrogen protection. Subsequently, acetonitrile (2.6 mL, 54.7 mmol) was added and stirring was continued at 0 °C for 30 min. In another reaction flask, AlCl3 (4.87 g, 36.5 mmol) was suspended in anhydrous dichloromethane (50 mL), cooled to 0 °C, and the aforementioned p-xylene solution was added dropwise through the addition funnel under nitrogen protection. After addition, the dichloromethane was removed under vacuum after stirring at 0°C for 45 minutes. The remaining p-xylene solution was heated to 70°C and maintained for 18 hours, followed by cooling to room temperature. Water (80 mL) was added and again heated to 70°C maintained for 1 hour and cooled to room temperature. The reaction mixture was diluted with ethyl acetate and the aqueous layer was separated. The organic layer was washed sequentially with equal volumes of water and saturated saline, dried over anhydrous MgSO4 and concentrated under reduced pressure. 1H), 7.03 (br.s., 2H), 7.65 (d, J = 9.04 Hz, 1H). LC-MS (ESI): m/z 180.10 (M + H)+.

References

[1] Patent: US2010/196321, 2010, A1. Location in patent: Page/Page column 20
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3021 - 3026
[3] Patent: WO2008/96002, 2008, A1. Location in patent: Page/Page column 82-83
[4] Patent: WO2008/92954, 2008, A2. Location in patent: Page/Page column 28-29
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 17, p. 4853 - 4858