5-BROMO-2-METHOXYANILINE Chemical Properties

Melting point:

94-96°C

Boiling point:

275℃

Density 

1.531

Flash point:

120℃

storage temp. 

2-8°C

pka

3.46±0.10(Predicted)

form 

powder to crystal

color 

Light yellow to Brown

Water Solubility 

Slightly soluble in water.

InChI

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

InChIKey

OPGNSNDTPPIYPG-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

6358-77-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-33-43-22

Safety Statements 

26-33-36/37/39-45-36/37

RIDADR 

UN2811

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

2921490090

MSDS

• Language:English Provider:ALFA

5-BROMO-2-METHOXYANILINE Usage And Synthesis

Chemical Properties

Off-white powder

Uses

5-Bromo-2-methoxyaniline is used as a pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 5-bromo-2-methoxyaniline from 2-nitro-4-bromoanisole: 1. Preparation of Intermediate 11A: An ethanol (65 mL) solution of 4-bromo-1-methoxy-2-nitrobenzene (2.00 g, 8.62 mmol), zinc powder (5.64 g, 86.0 mmol), and ammonium chloride (4.61 g, 86.0 mmol) was stirred for 2 hours at room temperature. 2. Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate (EtOAc) and filtered through diatomaceous earth (CELITE). 3. The filtrate was concentrated by evaporation to give Intermediate 11A (1.74 g, 100% yield) as an off-white solid. 4. Mass spectral analysis (LCMS-ESI) of Intermediate 11A showed m/z 202,204 ([M+H]? , [M+2+H]?) , and a retention time (RT) of 0.70 min (Method J).

References

[1] Patent: WO2014/22343, 2014, A1. Location in patent: Paragraph 00169
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1357 - 1366
[3] Journal fuer Praktische Chemie (Leipzig), 1935, vol. <2> 143, p. 18,24
[4] Gazzetta Chimica Italiana, 1932, vol. 62, p. 51,54
[5] Justus Liebigs Annalen der Chemie, 1883, vol. 217, p. 44

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