5-amino-2-bromo-4-methylbenzoic acid

5-amino-2-bromo-4-methylbenzoic acid Property

Boiling point:

380.2±42.0 °C(Predicted)

Density 

1.682±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2.16±0.10(Predicted)

Appearance

Light brown to brown Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

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

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

P362Take off contaminated clothing and wash before reuse.

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

P405Store locked up.

P501Dispose of contents/container to..…

5-amino-2-bromo-4-methylbenzoic acid Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 5-amino-2-bromo-4-methylbenzoic acid from 3-amino-4-methylbenzoic acid was as follows: 3-amino-4-methylbenzoic acid (24.72 g, 162 mmol) was dissolved in anhydrous DMF (140 mL). Subsequently, the solution was cooled to 0-5 °C and N-bromosuccinimide (29.70 g, 163.5 mmol) was added in batches while keeping the temperature of the reaction mixture below 15 °C. The reaction mixture was stirred under these conditions for 2 hours. Upon completion of the reaction, the mixture was slowly poured into an ice-water mixture (150 g) while stirring was continued. The precipitated solid was collected by filtration and washed with cold water (3 x 120 mL). The resulting filter cake was dissolved in EtOAc (800 mL) and the organic layer was washed with water (3 x 200 mL). The organic layer was subsequently dried with anhydrous magnesium sulfate, filtered and the solvent was removed by vacuum evaporation to afford 5-amino-2-bromo-4-methylbenzoic acid as a pink solid (31.59 g, 85% yield).

References

[1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 2662 - 2675
[2] Patent: WO2011/159067, 2011, A2. Location in patent: Page/Page column 28
[3] Patent: US2007/275907, 2007, A1. Location in patent: Page/Page column 19
[4] Patent: US2008/242596, 2008, A1. Location in patent: Page/Page column 15
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 19, p. 5632 - 5635