2,6-DIBROMOANISOLE Chemical Properties

Melting point:

13°C

Boiling point:

254℃

Density 

1.823

refractive index 

1.5920 to 1.5960

Flash point:

100℃

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow

InChI

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

InChIKey

BMZVDHQOAJUZJL-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

38603-09-7

Safety Information

HS Code 

2909303840

2,6-DIBROMOANISOLE Usage And Synthesis

Uses

2,6-Dibromoanisole is an anisole compound containing a substituent bromine atom that can be used in bromine substitution reactions to prepare other organic ether derivatives. It is also a Lusutrombopag intermediate, which is used to treat thrombocytopenia (low platelets in the blood) in adult patients with chronic liver disease who are scheduled to undergo medical or dental procedures.

Synthesis

Example 1 Preparation of 2,6-dibromo-4-(6-(3-bromobenzyloxy)pyridazin-3-yl)phenol (Compound 91): to a stirred solution of 2,6-dibromophenol (5.26 g, 20.9 mmol) in acetone (170 mL) was added anhydrous potassium carbonate (4.33 g, 31.3 mmol) and the mixture was stirred at room temperature for 30 minutes. Iodomethane (1.97 mL, 31.4 mmol) was then added and the reaction mixture was heated to reflux at 60 °C for 3 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated by rotary evaporation. The residue was extracted by partitioning between petroleum ether (40-60 °C, 100 mL) and water (100 mL). The aqueous layer was extracted once more with petroleum ether (40-60 °C, 100 mL), and the organic phases were combined, washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to afford 5.43 g (98% yield) of the target compound, 1 ,3-dibromo-2-methoxybenzene, as a colorless oil.1H NMR (CDCl3, δ ppm): 3.89 (3H, s), 6.86 (1H, t, J = 8.02 Hz), 7.50 (2H, d, J = 8.01 Hz).

References

[1] Tetrahedron Letters, 2008, vol. 49, # 33, p. 4912 - 4914
[2] Patent: US2009/270398, 2009, A1. Location in patent: Page/Page column 35
[3] Journal of the American Chemical Society, 2009, vol. 131, # 47, p. 17371 - 17375
[4] Journal of the American Chemical Society, 2016, vol. 138, # 31, p. 9779 - 9782
[5] Patent: WO2009/103440, 2009, A1. Location in patent: Page/Page column 75

2,6-DIBROMOANISOLE(38603-09-7)Related Product Information

• 2-Allyloxy-1,3,5-tribromobenzene
• 2,4,6-TRIBROMOPHENYL ACETATE
• Decabromodiphenyl oxide
• 1,2-Bis(2,4,6-tribromophenoxy)ethane
• BROMOXYNIL-METHYL ETHER
• 4,4'-Isopropylidenebis[2-(2,6-dibromophenoxy)ethanol]
• Bromoxynil octanoate
• Tetrabromobisphenol A bis(dibromopropyl ether)
• TRIBROMONEOPENTYL METHACRYLATE
• 3,5-DIBROMOANISOLE
• 2,4-DIBROMOANISOLE,2,4-Dibromoanisole, 98+%,4,6-Dibromoanisole
• 2,4-Dibromoanisole-5-boronic acid
• 2,4-Dibromoanisole-3-boronic acid
• 2,5-DIBROMOANISOLE
• BOC-3,5-DIBROMO-TYR(OBZL)-OH
• 2,4,6-TRIBROMO-3-METHOXYPHENOL
• 2,6-DIBROMO-4-FLUOROANISOLE
• 3,5-DIBROMO-4-METHOXYBENZOIC ACID