| Identification | More | [Name]
5-Bromoisatoic anhydride | [CAS]
4692-98-2 | [Synonyms]
5-BROMOISATOIC ANHYDRIDE
6-BROMO-1,2-DIHYDRO-4 H-3,1-BENZOXAZINE-2,4-DIONE
6-BROMO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE
AKOS BBS-00002893
BROMO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE
5-BROMOISATOIC ANHYDRIDE, TECH., 90%
5-Bromoisatoicacid
5-BROMOISATOIC ANHYDRIDE 90%
6-Bromo-2H-3,1-benzoxazine-2,4(1H)-dione | [EINECS(EC#)]
230-454-7 | [Molecular Formula]
C8H4BrNO3 | [MDL Number]
MFCD00016921 | [Molecular Weight]
242.03 | [MOL File]
4692-98-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white to salmon powder | [Melting point ]
280-285 °C (dec.) (lit.) | [density ]
1.826±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Dimethylformamide | [form ]
powder to crystal | [pka]
9.81±0.20(Predicted) | [color ]
White to Light yellow to Light orange | [CAS DataBase Reference]
4692-98-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xi | [Risk Statements ]
R61:May cause harm to the unborn child.
R20/21:Harmful by inhalation and in contact with skin .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT, IRRITANT-HARMFUL | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white to salmon powder | [Uses]
5-Bromoisatoic anhydride is an important chemical raw material and pharmaceutical intermediate, mainly used in laboratory research and development processes and chemical production processes. | [Preparation]
5-Bromoisatoic anhydride is prepared from 5-bromo indole by stirring in a 4:1 mixture of DMF/H2O for 16 h at room temperature.
1HNMR(DMSO-d6): δ 11.85 (s, br., 1H), 7.96 (dd, J = 0.8, 8.7 Hz, 1H), 7.87 (dd, J = 2.3, 8.7 Hz, 1H), 7.09 (dd, J = 8.8, 0.8 Hz, 1H). | [Synthesis]
General procedure for the synthesis of 6-bromo-2H-benzo[d][1,3]oxazine-2,4(1H)-dione using 5-bromoindigo red as starting material: 5-bromoindigo red (II) (20.0 g, 88.49 mmol) was uniformly dispersed in dichloromethane (300 mL), and m-chloroperoxybenzoic acid (22.91 g, 132.73 mmol) was added in batches at room temperature. at room temperature. The reaction mixture was stirred at room temperature for 2 h. The reaction progress was monitored by thin layer chromatography (TLC) to confirm the completion of the reaction. Subsequently, the reaction system was cooled to 10°C with continuous stirring and sodium bisulfite solution was slowly added dropwise until the starch potassium iodide paper no longer showed color. The reaction solution was concentrated by rotary evaporation to remove dichloromethane, 50 mL of water was added to mix well with the residue, and then saturated sodium bicarbonate solution was added dropwise until no bubbles were produced. The resulting solid was collected by filtration, washed with a small amount of water and dried at 50 °C to give 20.99 g of 5-bromoisatoindirubic anhydride (III) in 98% yield. | [References]
[1] Patent: CN106632276, 2017, A. Location in patent: Paragraph 0112; 0113; 0114
[2] Angewandte Chemie, 1980, vol. 92, # 3, p. 196 - 197
[3] Catalysis Science and Technology, 2015, vol. 5, # 10, p. 4830 - 4838
[4] Patent: CN103570726, 2016, B. Location in patent: Paragraph 0085; 0086; 0087
[5] Journal fuer Praktische Chemie (Leipzig), 1886, vol. <2> 33, p. 36 |
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