3-BROMO-4-METHOXYANILINE

3-BROMO-4-METHOXYANILINE Property

Melting point:

62 °C

Boiling point:

282.2±20.0 °C(Predicted)

Density 

1.531±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.13±0.10(Predicted)

color 

White to Brown

InChIKey

NMUFTXMBONJQTC-UHFFFAOYSA-N

CAS DataBase Reference

19056-41-8

Safety

Hazard Codes 

Xi,N,T+

Risk Statements 

26/27/28-33-50

Safety Statements 

28-36/37-45-61

RIDADR 

2811

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

2921420090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

3-BROMO-4-METHOXYANILINE Chemical Properties,Usage,Production

Uses

3-Bromo-4-methoxyaniline is an intermediate used to prepare triazole analogs of combretastatin A-4 as cytotoxic agents and inhibitors of tubulin. It is also used in the synthesis of (1,2,4-oxadiazolyl)biphenylcarbonyltetrahydrospiro[furo]indolepiperidine (SB-224289) as selective 5-HT1B receptor inverse agonist.

Synthesis

General procedure for the synthesis of 3-bromo-4-methoxyaniline from 2-bromo-4-nitroanisole: 2-bromo-4-nitroanisole (0.1 g, 0.43 mmol) was suspended in unstabilized 57% hydriodic acid (1.3 mL), and the reaction was heated for 5 hr at 90 °C. After completion of the reaction, the reaction mixture was cooled, diluted with ethyl acetate (5 mL) and washed sequentially with saturated aqueous sodium thiosulfate and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product was further purified by silica gel column chromatography to afford 3-bromo-4-methoxyaniline (0.07 g, 80% yield).

References

[1] ACS Catalysis, 2015, vol. 5, # 3, p. 1526 - 1529
[2] Patent: WO2011/98776, 2011, A1. Location in patent: Page/Page column 60
[3] Patent: US2013/53372, 2013, A1. Location in patent: Paragraph 0584; 0585
[4] Patent: US2007/123515, 2007, A1. Location in patent: Page/Page column 24
[5] Justus Liebigs Annalen der Chemie, 1883, vol. 217, p. 44