3,5-Dibromoanisole Chemical Properties

Melting point:

34-38 °C

Boiling point:

249.7°C

Density 

1.823

Flash point:

98.1°C

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Gray to Brown

Stability:

Stable. Incompatible with strong oxidizing agents.

InChI

InChI=1S/C7H6Br2O/c1-10-7-3-5(8)2-6(9)4-7/h2-4H,1H3

InChIKey

OQZAQBGJENJMHT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

74137-36-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2909303890

3,5-Dibromoanisole Usage And Synthesis

Chemical Properties

solid

Uses

3,5-Dibromoanisole, is an organic building block used for the synthesis of various pharmaceutical compounds, such as Dicationic m-Terphenyl and 1,3-Dipyridylbenzene Derivatives, having Antiprotozoal Activity.

Synthesis

The general procedure for the synthesis of 3,5-dibromoanisole from methanol and 1,3-dibromo-5-nitrobenzene was as follows: 1,3-dibromo-5-nitrobenzene (21.07 g, 75 mmol), freshly powdered potassium hydroxide (7.57 g, 135 mmol) and tetrabutyl ammonium bromide (2.42 g, 7.5 mmol) were suspended in tetramethylurea (80 mL). A solution of methanol (4.81 g, 6.09 mL, 150 mmol) dissolved in 20 mL of tetramethylurea was added slowly and dropwise to the above brown suspension over a period of 15 min at room temperature. The reaction mixture was stirred continuously for 24 h at room temperature before it was quenched by pouring it into ice (150 g) and extracted with tert-butyl methyl ether (3 x 250 mL). The organic phases were combined, dried with magnesium sulfate and subsequently concentrated under reduced pressure to give the crude product. The crude product was purified by reduced pressure distillation (124 °C, 10 Torr) to give 16.74 g (84% yield) of 3,5-dibromoanisole as a light yellow solid.

References

[1] Patent: US2006/270686, 2006, A1. Location in patent: Page/Page column 35
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 179 - 200
[3] Patent: US2008/280891, 2008, A1. Location in patent: Page/Page column 34-35
[4] Patent: WO2008/8059, 2008, A1. Location in patent: Page/Page column 96

3,5-Dibromoanisole(74137-36-3)Related Product Information

• 3,5-Dibromobenzoic acid
• 4-Methoxyphenol
• 2-Bromoanisole
• 3-Bromoanisole
• 4-Methylanisole
• 4-Bromoanisole
• 3,5-Difluoroanisole
• 3,5-Dimethylanisole
• 1,3-Dibromopropane
• 2,5-Dibromopyrazine
• Anisole
• 2,3-Dibromopropionic acid
• Decabromodiphenyl oxide
• PENTABROMOPHENYL ACRYLATE
• OCTABROMODIPHENYL ETHER
• 2,2',3,3',4,4',5,5',6-nonabromodiphenylether
• PENTABROMOPHENYL METHACRYLATE
• 2,6-Dibromo-4-(trifluoromethoxy)aniline