ChemicalBook Product Catalog Organic Chemistry 1-Bromo-2,5-dimethoxybenzene

1-Bromo-2,5-dimethoxybenzene

Product Name1-Bromo-2,5-dimethoxybenzene
CAS25245-34-5
MFC8H9BrO2
MW217.06
EINECS246-756-7
MOL File25245-34-5.mol

Chemical Properties

Boiling point	130-131 °C/10 mmHg (lit.)
Density	1.445 g/mL at 25 °C (lit.)
refractive index	1.569-1.571
Flash point	>110°C
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
form	clear liquid
color	Colorless to Light yellow
Specific Gravity	1.445
Water Solubility	Insoluble in water.
BRN	2441884
InChI	InChI=1S/C8H9BrO2/c1-10-6-3-4-8(11-2)7(9)5-6/h3-5H,1-2H3
InChIKey	DWCGNRKFLRLWCJ-UHFFFAOYSA-N
SMILES	C1(OC)=CC=C(OC)C=C1Br
CAS DataBase Reference	25245-34-5(CAS DataBase Reference)
NIST Chemistry Reference	1-Bromo-2,5-dimethoxybenzene(25245-34-5)
EPA Substance Registry System	Benzene, 2-bromo-1,4-dimethoxy- (25245-34-5)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	37/39-26
WGK Germany	3
TSCA	TSCA listed
HazardClass	IRRITANT
HS Code	29039990
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
1-Bromo-2,5-dimethoxybenzene	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

clear colorless to yellowish liquid

Uses

1-Bromo-2,5-dimethoxybenzene has been used in preparation of:

S-(-)-2-[N-(trifluoroacetyl)amino]-1-(2,5-dimethoxy-4- bromophenyl)-1-propanone
1,4-bis{4-[2-(4-pyridyl)ethenyl]phenyl}butadiyne and 1,4-bis{2,5-dimethoxy-4-[2-(4-pyridyl)ethenyl]phenyl}butadiyne
1-bromo-4-iodo-2,5-dimethoxybenzene

Uses

2-Bromo-1,4-dimethoxybenzene has been used in preparation of S-(-)-2-[N-(trifluoroacetyl)amino]-1-(2,5-dimethoxy-4- bromophenyl)-1-propanone, 1,4-bis{4-[2-(4-pyridyl)ethenyl]phenyl}butadiyne and 1,4-bis{2,5-dimethoxy-4-[2-(4-pyridyl)ethenyl]phenyl}butadiyne and 1-bromo-4-iodo-2,5-dimethoxybenzene. It can be used as a chemical redox shuttle additive in Lithium ion batteries for repeated overcharge and overdischarge protection.

Synthesis

17332-11-5

74-88-4

25245-34-5

2-Bromo-4-methoxyphenol (13.3 g, 65 mmol) and potassium carbonate (35.9 g, 260 mmol) were suspended in dry acetone (100 mL) under nitrogen protection. Under cooling in an ice bath, iodomethane (11.1 g, 3.1 mmol) was slowly added. After addition, the reaction mixture was gradually warmed to room temperature with continuous stirring overnight. After completion of the reaction, the potassium carbonate was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by fast column chromatography (eluent: petroleum ether/ethyl acetate, 30:1, v/v) to afford 1-bromo-2,5-dimethoxybenzene (13.9 g, 97.9% yield) as a colorless oil.

References

[1] Heterocycles, 2018, vol. 96, # 2, p. 334 - 338

Preparation Products And Raw materials

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