1-Bromo-3,4,5-trimethoxybenzene Chemical Properties

Melting point:

78-82 °C(lit.)

Boiling point:

273°C/747mmHg(lit.)

Density 

1.5463 (rough estimate)

refractive index 

1.4730 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Light yellow to Light orange

Water Solubility 

Insoluble in water.

InChI

InChI=1S/C9H11BrO3/c1-11-7-4-6(10)5-8(12-2)9(7)13-3/h4-5H,1-3H3

InChIKey

XAOOZMATJDXDQJ-UHFFFAOYSA-N

SMILES

C1(OC)=CC(Br)=CC(OC)=C1OC

CAS DataBase Reference

2675-79-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

22-36/37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2909309090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-Bromo-3,4,5-trimethoxybenzene Usage And Synthesis

Uses

5-Bromo-1,2,3-trimethoxybenzene is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Synthesis

The general procedure for the synthesis of 1-bromo-3,4,5-trimethoxybenzene from methyl p-bromobenzoate and 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborole cyclohexane is as follows: aryl halide (0.67 mmol, 1.0 eq.), aryl boronate (0.81 mmol, 1.2 eq.) were added to a Schlenk tube in the following order, potassium phosphate or CsF (3.0 eq.), Pd catalyst (0.1 eq.) and 2-(dicyclohexylphosphino)biphenyl (0.2 eq.). When using Pd(OAc)2 as the catalyst, CsF is required as the base (see Table 8, entries 13-15). Subsequently, a PTFE-coated stirrer was added to the reaction system and the reaction was carried out at room temperature. The reaction mixture was degassed under high vacuum three times for 10 min each and backfilled with nitrogen. Anhydrous dioxane was added through the T-neck and the reaction mixture was heated to 110°C and kept for 18 hours. Upon completion of the reaction, the mixture was cooled to room temperature and diluted with dichloromethane (10 mL). The reaction solution was filtered and the filtrate was washed with dichloromethane (100 mL). Finally, the filtrate was concentrated and purified by silica gel column chromatography.

References

[1] Patent: WO2009/137322, 2009, A2. Location in patent: Page/Page column 21; 22; 29; 30; 31

1-Bromo-3,4,5-trimethoxybenzene(2675-79-8)Related Product Information

• o-Anisaldehyde
• 4-Methoxybenzoic acid
• 2-Bromobenzonitrile
• 4-Methoxybenzyl cyanide
• 3,4,5-Trimethoxy benzoic acid
• p-Anisaldehyde
• 3,4,5-Trimethoxyphenylacetic acid
• (Trifluoromethoxy)benzene
• 1,2,4-Trimethoxybenzene
• Anisole
• 4-Bromofluorobenzene
• 3-Bromoanisole
• 3-Methoxybenzaldehyde
• m-Anisyl alcohol
• 1,2,3-Trimethoxybenzene
• 1,3,5-Trimethoxybenzene
• 4'-Bromopropiophenone
• 1,3-Dibromobenzene