| Identification | More | [Name]
4-Bromophthalic anhydride | [CAS]
86-90-8 | [Synonyms]
1,3-ISOBENZOFURANDIONE, 5-BROMO-
4-BPA
4-BROMOPHTHALIC ACID ANHYDRIDE
4-BROMOPHTHALIC ANHYDRIDE
TIMTEC-BB SBB008534
5-Bromo-1,3-isobenzofurandione
4-BrPA
4-Bromo-1,2-benzenedicarboxylic anhydride
5-Bromoisobenzofuran-1,3-dione
5-Bromophthalic anhydride | [EINECS(EC#)]
201-707-9 | [Molecular Formula]
C8H3BrO3 | [MDL Number]
MFCD00191323 | [Molecular Weight]
227.01 | [MOL File]
86-90-8.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to white powder | [Melting point ]
107 °C | [Boiling point ]
301 °C | [density ]
1.911 | [storage temp. ]
Inert atmosphere,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 Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [HS Code ]
29173990 |
| Hazard Information | Back Directory | [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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