Methyl 5-bromo-2-hydroxy-3-nitrobenzenecarboxylate

Methyl 5-bromo-2-hydroxy-3-nitrobenzenecarboxylate Property

storage temp. 

Sealed in dry,Room Temperature

form 

solid

color 

Pale yellow

Safety

HazardClass 

IRRITANT

HS Code 

2918290090

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.

Methyl 5-bromo-2-hydroxy-3-nitrobenzenecarboxylate Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of methyl 5-bromo-2-hydroxy-3-nitrobenzoate from methyl 5-bromo-2-hydroxybenzoate was as follows: Methyl 5-bromo-2-hydroxybenzoate (231 g, 1 mol) was dissolved in concentrated sulfuric acid (500 mL), and cooled down in an ice bath to 0 °C. A mixture of concentrated nitric acid (108 g, 1.1 mol) and concentrated sulfuric acid (120 mL) was added to the above cooled down solution slowly by dropwise addition. The mixture of concentrated nitric acid (108 g, 1.1 mol) and concentrated sulfuric acid (120 mL) was slowly added dropwise to the above cooled solution at 0°C, and the rate of acceleration of the dropwise acceleration was controlled so as to maintain the temperature of the reaction system not exceeding 5°C. After the dropwise acceleration was completed, the ice bath was removed, and the reaction system was allowed to warm up to room temperature naturally, and the reaction was continued at room temperature for 3.5 hrs. The progress of the reaction was monitored by thin layer chromatography (TLC), and after confirming the completion of the reaction, the reaction mixture was slowly poured into crushed ice (2 L) and stirred until the crushed ice completely melted, at which time a large amount of light yellow solid precipitated from the system. The solid was collected by filtration, washed to neutrality with ice water and dried to give methyl 5-bromo-2-hydroxy-3-nitrobenzoate (243 g) as a light yellow solid in 88% yield.

References

[1] Patent: CN107573336, 2018, A. Location in patent: Paragraph 0096; 0097; 0098
[2] Patent: US2009/197863, 2009, A1. Location in patent: Page/Page column 56
[3] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 3, p. 624 - 630