6-Bromoindazole Chemical Properties

Melting point:

180-182

Boiling point:

333.8±15.0 °C(Predicted)

Density 

1.770±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

12.78±0.40(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C7H5BrN2/c8-6-2-1-5-4-9-10-7(5)3-6/h1-4H,(H,9,10)

InChIKey

WMKDUJVLNZANRN-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(Br)=C2)C=N1

CAS DataBase Reference

79762-54-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-41

Safety Statements 

26-36/37-39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

6-Bromoindazole Usage And Synthesis

Uses

6-Bromo-1H-indazole is an indazole derivative being studied as an inhibitor of DNA gyrase B and its antibacterial activity.

Synthesis

General procedure for the synthesis of 6-bromo-1H-indazole from 4-bromo-2-fluorobenzaldehyde: Hydrazine hydrate (30 mL, 832 mmol) and 4-bromo-2-fluorobenzaldehyde (4.69 g, 23 mmol) were added to a 100 mL round bottom flask. The reaction mixture was stirred at 125 °C for 3 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction solution was subsequently concentrated under reduced pressure. The concentrated reaction solution was quenched by pouring it into an ice-water mixture (100 mL) and then extracted with ethyl acetate (3 × 100 mL). The organic phases were combined, dried over anhydrous sodium sulfate, and filtered to remove the desiccant. The filtrate was concentrated to dryness under reduced pressure, and the resulting crude product was adsorbed on silica gel. The crude product was purified by column chromatography using a Redi-Sep pre-populated silica gel column (40 g) with hexane/ethyl acetate (0 to 100% gradient) as eluent to give the final 6-bromo-1H-indazole (4.6 g, 18 mmol, 76% yield). The product was detected by LCMS, [M + H]+ m/z 197.9 (calculated value C7H5BrN2 197.0).1H NMR (400 MHz, CD3OD): δ 8.03 (s, 1H), 7.67-7.72 (m, 2H), 7.24-7.26 (m, 1H).

References

[1] Patent: CN106146401, 2016, A. Location in patent: Paragraph 0117; 0190; 0191
[2] Patent: US2015/368278, 2015, A1. Location in patent: Paragraph 1273; 1274
[3] Journal of Organic Chemistry, 2006, vol. 71, # 21, p. 8166 - 8172
[4] Patent: US2007/173506, 2007, A1. Location in patent: Page/Page column 48
[5] Organic Process Research and Development, 2011, vol. 15, # 3, p. 565 - 569

6-Bromoindazole(79762-54-2)Related Product Information

• 1-Boc-5-bromoindazole
• 6-Bromoindazole
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• 6-BROMO INDAZOLE-3-CARBOXYLIC ACID
• 6-BROMO-1H-INDAZOLE-3-CARBONITRILE
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• 5-AMINO-3-BROMOINDAZOLE
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• 5-BROMOINDAZOLE
• Indazole
• 6-BROMO-4-INDAZOLECARBOXYLIC ACID METHYL ESTER
• METHYL 6-BROMO-1H-INDAZOLE-3-CARBOXYLATE
• 3 ALDEHYDE, 4-METHYL ESTER, 6-BROMOINDAZOLE
• 4,6-DIBROMO-1H-INDAZOLE