7-BROMO-1H-INDOLE-2,3-DIONE Chemical Properties

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 Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933998090

7-BROMO-1H-INDOLE-2,3-DIONE Usage And Synthesis

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

7-BROMO-1H-INDOLE-2,3-DIONE(20780-74-9)Related Product Information

• 5-Bromoisatoic anhydride
• 5-BROMO-1H-INDOLE-2,3-DIONE
• 4-BROMO-1H-INDOLE-2,3-DIONE
• 4-Bromoindole-3-carboxaldehyde 98%,4-BROMOINDOLE-3-CARBOXALDEHYDE
• 6-BROMOINDOLE-3-CARBOXALDEHYDE
• 7-BROMO-5-METHYL-1H-INDOLE-2,3-DIONE
• 7-BROMO-1H-INDOLE-2,3-DIONE
• 6-Bromoisatinic anhydride
• 5-Bromoindole-3-carboxaldehyde 97%,5-BROMOINDOLE-3-CARBOXALDEHYDE, 98+%,5-BROMOINDOLE-3-CARBOXALDEHYDE
• 4-BROMOINDOLE-3-CARBOXALDEHYDE, N-BOC PROTECTED
• 5-Bromoindole-3-carboxaldehyde, N-BOC protected 98%,5-BROMOINDOLE-3-CARBOXALDEHYDE, N-BOC PROTECTED
• 6-BROMO-1H-INDOLE-2,3-DIONE,6-BROMO-1H-INDOLE-2,3-DIONE 97.0%(MIN)(HPLC)
• 4-Bromoisatoic anhydride
• Isatin
• CHEMBRDG-BB 5226017
• 1-Benzyl-5-bromo-1H-indole-2,3-dione
• 1-Methyl-5-bromo-1H-indole-2,3-dione
• 7-Bromoindole-3-carboxaldehyde