2-Bromo-4,5-dimethoxyphenol

2-Bromo-4,5-dimethoxyphenol Property

Melting point:

96.0 to 100.0 °C

Boiling point:

285.3±35.0 °C(Predicted)

Density 

1.532±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

8.56±0.23(Predicted)

color 

Light yellow to Brown

CAS DataBase Reference

129103-69-1

Safety

HS Code 

2908.19.6000

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.

P321Specific treatment (see … on this label).

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

P362Take off contaminated clothing and wash before reuse.

2-Bromo-4,5-dimethoxyphenol Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 2-bromo-4,5-dimethoxyphenol from 3,4-dimethoxyphenol was as follows: 4-bromoanisole (200.8 mg, 1.09 mmol, 1.0 eq.) was dissolved in acetonitrile (2 mL) at room temperature, followed by addition of N-chlorosuccinimide (NCS) (158.3 mg, 1.19 mmol, 1.1 eq.) , a slightly turbid mixture was obtained. Next, chlorotrimethylsilane (TMSCl) (14 μL, 0.11 mmol, 0.1 eq.) was added dropwise to the reaction mixture. Within a few minutes, the reaction mixture was transformed into a clarified pale yellow solution. Stirring of the reaction mixture was continued at room temperature for 1 h, after which it was diluted with hexane. The two-phase mixture was concentrated on a rotary evaporator to give a crude white solid-oil mixture. This mixture was dissolved in hexane, filtered through a short silica gel column and eluted with 5-10% ethyl acetate-hexane solution. Concentration of the clarified filtrate afforded a mixture of 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2,4-dichloro-1-methoxybenzene (2a-diCl) in a yield of 237.0 mg (based on NMR analysis of a ratio of 2a-Cl to 2a-diCl of 7.1:1.0, with 88% yield of 2a-Cl and 11% yield of 2a-diCl ), and the product was a light yellow solid.

References

[1] Synlett, 2014, vol. 25, # 12, p. 1769 - 1775
[2] Patent: CN106632268, 2017, A. Location in patent: Paragraph 0024; 0025; 0026