1,4-Dibromo-2,5-dimethoxybenzene Chemical Properties

Melting point:

144-149 °C (lit.)

Boiling point:

290.3±35.0 °C(Predicted)

Density 

2,24 g/cm³

refractive index 

1.4947 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Almost white

Water Solubility 

Insoluble in water.

BRN 

1953103

InChI

InChI=1S/C8H8Br2O2/c1-11-7-3-6(10)8(12-2)4-5(7)9/h3-4H,1-2H3

InChIKey

CHCLRVOURKGRSW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2674-34-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2909303890

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

1,4-Dibromo-2,5-dimethoxybenzene Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

1,4-Dibromo-2,5-dimethoxybenzene was used in the preparation of poly[(9,9-bis(6-(dibromohexyl)-2,7-fluorene))-alt-1,4-(2,5-dimethoxybenzene)], a water-soluble polyfluorene derivative.

Synthesis Reference(s)

The Journal of Organic Chemistry, 63, p. 3764, 1998 DOI: 10.1021/jo9721812

General Description

Crystal structure of 1,4-dibromo-2,5-dimethoxybenzene has been reported to be monoclinic and its asymmetric unit is composed of one-half of the molecule. Lithium diisopropylamide (LDA) mediated metallation of 1,4-dibromo-2,5-dimethoxybenzene has been proposed.

Synthesis

Example 2: Preparation of 2,5-dibromo-1,4-dimethoxybenzene (2); In a 1 liter round-bottomed flask, a solution of chloroform (50 mL) of bromine (35.2 g, 220 mmol) was added slowly and dropwise to a solution of chloroform (400 mL) of 1,4-dimethoxybenzene (13.8 g, 100 mmol). The reaction mixture was stirred at room temperature for 3 hours before 100 mL of saturated Na2CO3 solution was added to quench the reaction. The organic layer was separated, washed sequentially with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the resulting residue was recrystallized from ethanol to give pure 2,5-dibromo-1,4-dimethoxybenzene (25.8 g, 85% yield). The product was characterized by 1H NMR (CDCl3): δ 7.128 (s, 2H), 3.873 (s, 6H).

References

[1] Tetrahedron, 1999, vol. 55, # 36, p. 11127 - 11142
[2] Tetrahedron Letters, 1998, vol. 39, # 35, p. 6349 - 6350
[3] Organic Process Research and Development, 2016, vol. 20, # 2, p. 284 - 296
[4] Journal of the American Chemical Society, 2003, vol. 125, # 37, p. 11241 - 11248
[5] Journal of Materials Chemistry A, 2017, vol. 5, # 44, p. 22933 - 22938

1,4-Dibromo-2,5-dimethoxybenzene(2674-34-2)Related Product Information

• 3,4-Dimethoxyphenol
• Phthalic anhydride
• Dimethyldimethoxysilane
• Dibutyl phthalate
• Anisole
• (Trifluoromethoxy)benzene
• 3,5-Dimethoxyphenol
• 1,3-Dimethoxybenzene
• 2-Phenoxyethanol
• O-Phthalimide
• Phthalates
• 1,3-Dibromo-4,6-Dimethoxybenzene,1,5-Dibromo-2,4-dimethoxybenzene
• 1,2-DIBROMO-4,5-DIMETHOXYBENZENE
• TETRADECABROMO-1,4-DIPHENOXYBENZENE
• 1,4-Dibromo-2,5-dimethoxybenzene
• 2,5-BIS[2-(N,N-DIETHYLAMINO)-ETHOXY]-1,4-DIBROMOBENZENE
• 1,4-DIBROMO-2,5-BIS(DECYLOXY)BENZENE
• 1,4-DIBROMO-2,5-BIS(3-SULFONATOPROPOXY)BENZENE DISODIUM SALT