4-BROMO PHTHALIC ANHYDRUS Chemical Properties

Melting point:

107 °C

Boiling point:

301 °C

Density 

1.911

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

very soluble in Benzene

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C8H3BrO3/c9-4-1-2-5-6(3-4)8(11)12-7(5)10/h1-3H

InChIKey

BCKVHOUUJMYIAN-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=C(Br)C=C2)C(=O)O1

CAS DataBase Reference

86-90-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

29173990

4-BROMO PHTHALIC ANHYDRUS Usage And Synthesis

Chemical Properties

off-white to white powder

Synthesis

To a suspension of phthalic anhydride (1) (22 g, 148.5 mmol, 1.0 eq.) in water (150 mL) was slowly added sodium hydroxide (12 g, 300.0 mmol, 2.0 eq.) and pure bromine (8.5 mL, 165.9 mmol, 1.1 eq.). The reaction mixture was stirred at 90 °C for 12 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and filtered to collect a pale yellow solid. After washing the solid with cold water (50 mL), it was dissolved in sulfur dioxide (60 mL) and the mixture was heated to reflux for 5 hours. The reaction mixture was concentrated and dichloromethane (200 mL) was added to the residue and stirred at room temperature for 2 hours. After filtration, the filtrate was concentrated to give 5-bromoisobenzofuran-1,3-dione (2) (20 g, 71% yield) as a yellow solid.1H NMR (400 MHz, CDCl3) δ 8.16-8.17 (m, 1H), 8.06-8.07 (m, 1H), 7.89-7.90 (m, 1H).

References

[1] Patent: CN105399712, 2016, A. Location in patent: Paragraph 0025
[2] Patent: US2010/204214, 2010, A1. Location in patent: Page/Page column 109
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 1142 - 1150
[4] Patent: WO2018/95260, 2018, A1. Location in patent: Paragraph 058; 060; 0116
[5] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3417 - 3423

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