4-BROMO-2-METHOXY-PHENYLAMINE Chemical Properties

Melting point:

59 °C

Boiling point:

250.4±20.0 °C(Predicted)

Density 

1.531±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in methanol.

pka

3.83±0.10(Predicted)

form 

solid

color 

White to Orange to Green

InChI

InChI=1S/C7H8BrNO/c1-10-7-4-5(8)2-3-6(7)9/h2-4H,9H2,1H3

InChIKey

WRFYIYOXJWKONR-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

59557-91-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43-52

Safety Statements 

36/37

RIDADR 

UN2811/6.1/IIIPG

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

2922290090

4-BROMO-2-METHOXY-PHENYLAMINE Usage And Synthesis

Chemical Properties

Black particles

Uses

4-Bromo-2-methoxyaniline is used as a reagent in the synthesis of 3,5-diamino-1,2,4-triazole ureas as potent anaplastic lymphoma kinase (ALK) inhibitors. It is also used as a reagent in the synthesis of chroman-3-amides as potent Rho kinase inhibitors. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 32, p. 1936, 1989 DOI: 10.1021/jm00128a041

Synthesis

General procedure for the synthesis of 2-methoxy-4-bromoaniline and 2,4-dibromo-6-methoxyaniline from o-methoxyaniline: o-methoxyaniline (470 mg, 3.60 mmol) was dissolved in dichloromethane (8 mL) and cooled to -10 °C. 2,4,4,6-tetrabromocyclohexanedione (1.56 g, 3.60 mmol) was added slowly under stirring, keeping the reaction temperature below -5 °C. The reaction mixture was gradually warmed to room temperature and stirring was continued overnight. Upon completion of the reaction, the reaction mixture was washed sequentially with 2M sodium hydroxide solution (10 mL) and water (15 mL), then dried over magnesium sulfate, filtered and concentrated to dryness. The residue was separated by silica gel column chromatography (eluent: dichloromethane) and first eluted to give 2,4-dibromo-6-methoxyaniline (90 mg, 9% yield) as a dark brown liquid. Its 1H NMR (400 MHz, CDCl3) data were as follows: δ 3.84 (s, 3H, OCH3), 4.20 (br s, 2H, NH2), 6.83 (d, J = 2.1 Hz, 1H, ArH), 7.19 (d, J = 2.1 Hz, 1H, ArH), which is in accordance with the literature reports. Continued elution gave 4-bromo-2-methoxyaniline (579 mg, 83% yield) as a brown solid with a melting point of 57-59 °C (literature values: 56.5-58 °C and 60-61 °C). Its 1H NMR (400 MHz, CDCl3) data were as follows: δ 3.83 (s, 3H, OCH3), 3.85 (br s, 2H, NH2), 6.60 (d, J = 7.8 Hz, 2H, ArH), and 6.88-6.90 (m, 2H, ArH), which is in accordance with the literature reports. Ref: J.-M. Chretien, F. Zammattio, E. Le Grognec, M. Paris, B. Cahingt, G. Montavon, and J.-P. Quintard, J. Org. Chem. 70 (2005), pp. 2870-2873.

References

[1] Tetrahedron, 2011, vol. 67, # 32, p. 5798 - 5805
[2] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2870 - 2873

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