ChemicalBook Product Catalog Organic Chemistry Ethers and derivatives Ethers, ether-alcohols, ether phenol derivatives 3-Bromoanisole

3-Bromoanisole

Product Name3-Bromoanisole
CAS2398-37-0
MFC7H7BrO
MW187.03
EINECS219-264-5
MOL File2398-37-0.mol

Chemical Properties

Melting point	2 °C
Boiling point	211 °C
Density	1.49
vapor pressure	38.39Pa at 25℃
refractive index	1.56
Flash point	98 °C
storage temp.	Sealed in dry,Room Temperature
solubility	DMSO (Sparingly), Methanol (Slightly)
form	clear liquid
color	Colorless to Light yellow to Light orange
Specific Gravity	1.477
PH	5.5 (H2O, 20℃)
Water Solubility	Miscible in methanol, benzene, hexane, toluene and dichloromethane. Practically insoluble in water.
BRN	1524687
Henry's Law Constant	7.2×10^-3 mol/(m³Pa) at 25℃, Pfeifer et al. (2001)
Stability	Stable. Combustible. Incompatible with strong oxidising agents, strong acids reducing agents.
InChI	1S/C7H7BrO/c1-9-7-4-2-3-6(8)5-7/h2-5H,1H3
InChIKey	PLDWAJLZAAHOGG-UHFFFAOYSA-N
SMILES	COc1cccc(Br)c1
LogP	3.03
CAS DataBase Reference	2398-37-0(CAS DataBase Reference)
NIST Chemistry Reference	Benzene, 1-bromo-3-methoxy-(2398-37-0)
EPA Substance Registry System	m-Bromoanisole (2398-37-0)

Safety Information

Hazard Codes	Xi
Safety Statements	23-24/25
WGK Germany	3
F	8
Hazard Note	Irritant
TSCA	TSCA listed
HS Code	29093038
Storage Class	10 - Combustible liquids
Hazard Classifications	Aquatic Chronic 3

MSDS

Provider	Language
1-Bromo-3-methoxybenzene	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

3-Bromoanisole, also known as m-Bromoanisole, is a clear colorless to pale yellow oily liquid. The boiling point is 210-211°C (100kPa), 105°C (2.13kPa), the relative density is 1.477, the refractive index is 1.5635, and the flash point is 93°C. It is soluble in alcohol, ether, benzene, and carbon disulfide, but insoluble in water. It is commonly used as a raw material for organic synthesis.

Uses

3-Bromoanisole used in chemical reaction as intermediates to obtain target materials such as dyes, pharmaceuticals, perfumes, photoinitiators and agrochemicals.

Preparation

3-Bromoanisole is synthesized through a reaction between m-bromophenol and dimethyl sulfate. The synthesis method involves the following steps:
Dissolve m-bromophenol in a sodium hydroxide solution.
Slowly add dimethyl sulfate dropwise to the solution while stirring.
Heat the mixture and allow it to react for 1 hour.
Cool the reaction mixture to separate the colorless oil formed.
Extract the water layer with ether.
Dry the ether extract and then distill it to recover the ether.
Distill the residue obtained after recovering the ether, along with the colorless oil, under reduced pressure.
This distillation process results in the production of m-bromoanisole as the final product.
The overall yield of m-bromoanisole achieved through this process is 90%.

Synthesis

Iodonium, (3-methoxyphenyl)(2,4,6-trimethylphenyl)-, 1,1,1-trifluoromethanesulfonate (1:1)

1464149-60-7

2398-37-0

GENERAL METHOD: A mixture of diaryliodonium salt (0.5 mmol), methylene halide (0.75 mmol) and acetonitrile (1 mL) was placed in a 10 mL reaction tube and heated at 80°C for 2 hours with vigorous stirring. After completion of the reaction (monitored by TLC or GC), the reaction mixture was cooled to room temperature and 5 mL of water was added. The mixture was stirred for 10 min and the product was extracted with ethyl acetate (3 x 10 mL). The organic layer was washed with water and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with petroleum ether and ethyl acetate as eluents to give the pure m-bromoanisole. The structure of the product was confirmed by 1H NMR and 13C NMR analysis.

References

Application of Anisole, 2-Bromoanisole and 3-Bromoanisole as Overcharge Protection Additives in Lithium-Ion Batteries DOI:10.6023/A12110964
S. Ramalingam; S. Periandy. Spectroscopic investigation, computed IR intensity, Raman activity and vibrational frequency analysis on 3-bromoanisole using HF and DFT (LSDA/MPW1PW91) calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2011, 78 (2), 835-843. DOI:10.1016/j.saa.2010.12.043
Bobby Glover; Kimberly A. Harvey; Bing Liu; Matthew J. Sharp; and Maria F. Tymoschenko. Regioselective Palladium-Catalyzed Arylation of 3-Carboalkoxy Furan and Thiophene. Org. Lett. 2003, 5 (3), 301-304. DOI:10.1021/ol027266q

3-Bromoanisole

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