| Identification | More | [Name]
7-BROMO-1H-INDOLE-2,3-DIONE | [CAS]
20780-74-9 | [Synonyms]
7-BROMO-1H-INDOLE-2,3-DIONE
7-BROMO-2,3-DIOXOINDOLINE
7-BROMOINDOLINE-2,3-DIONE
7-BROMO-ISATIN
BUTTPARK 50\07-96
7-Bromoisatin 97%
7-BROMOINDOLE-3-CARBOXALDEHYDE
7-Bromoindoline-2,3-dione, 7-Bromo-1H-indole-2,3-dione
7-Bromoindole-1H-2,3-dione | [EINECS(EC#)]
625-256-6 | [Molecular Formula]
C8H4BrNO2 | [MDL Number]
MFCD00774354 | [Molecular Weight]
226.03 | [MOL File]
20780-74-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
191-198 °C | [density ]
1.826±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Slightly soluble. | [form ]
powder to crystal | [pka]
8.69±0.20(Predicted) | [color ]
Orange to Amber to Dark red | [InChI]
InChI=1S/C8H4BrNO2/c9-5-3-1-2-4-6(5)10-8(12)7(4)11/h1-3H,(H,10,11,12) | [InChIKey]
OCVKSIWBTJCXPV-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC=C2Br)C(=O)C1=O | [CAS DataBase Reference]
20780-74-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HS Code ]
2933998090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
7-bromoisatin was treated with excess PhMgBr to afford tertiary alcohol 9 in 96 % yield. Isatin oxime triflates undergo a facile fragmentation which is promoted by DBU, to form anthranilonitriles after hydrolytic work-up. | [Synthesis]
Step 2: N-(2-bromophenyl)-2-(hydroxyimino)acetamide (7 g, 0.028 mol) was slowly added to 70 mL of concentrated sulfuric acid, and the temperature of the reaction system was maintained at 60 °C. Subsequently, the reaction temperature was raised to 90 °C with continuous stirring for 3 hours. Upon completion of the reaction, the reaction mixture was slowly poured into ice water and a yellow precipitate was precipitated. The precipitate was collected by filtration and dried to give 7-bromoisatin as a yellow solid (6.0 g, 92% yield). The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 11.33 (s, 1H), 7.79 (d, J = 8.1 Hz, 1H), 7.52 (d, J = 7.2 Hz, 1H), 7.02 (t, J = 7.5 Hz, 1H); LC-MS (ESI) analysis: calculated mass: 224.9; observed mass: 226.0 [M + H]+ (retention time: 0.39 min). | [References]
[1] Patent: WO2012/58671, 2012, A1. Location in patent: Page/Page column 106
[2] Patent: CN105732462, 2016, A. Location in patent: Paragraph 0026
[3] Patent: CN103864779, 2016, B. Location in patent: Paragraph 0066; 0067; 0069
[4] Patent: WO2011/119704, 2011, A1. Location in patent: Page/Page column 38
[5] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 1, p. 22 - 26 |
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