3-Bromo-7-nitroindazole is a more potent and selective inhibitor of neuronal nitric oxide synthase (nNOS) than eNOS or inducible nitric oxide synthase (iNOS). 3-Bromo-7-nitroindazole affects the intercellular messenger nitric oxide (NO) synthesis throughout the body and brain.

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Quality Control of 3-Bromo-7-nitroindazole Purity: 98% SDS Specification

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Product Details of 3-Bromo-7-nitroindazole

CAS No. :	74209-34-0
Formula :	C₇H₄BrN₃O₂
M.W :	242.03
SMILES Code :	O=[N+](C1=CC=CC2=C1NN=C2Br)[O-]
MDL No. :	MFCD00159910
InChI Key :	NFSTZPMYAZRZPC-UHFFFAOYSA-N
Pubchem ID :	1649

Safety of 3-Bromo-7-nitroindazole

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 3-Bromo-7-nitroindazole

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 74209-34-0 ]

[ 74209-34-0 ] Synthesis Path-Downstream 1~28

1
[ 101860-76-8 ]
[ 74209-34-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1927,vol. 451,p. 285,302.

2
[ 2942-42-9 ]
[ 74209-34-0 ]

References: [1]Tetrahedron,2005,vol. 61,p. 8218 - 8225.
[2]Justus Liebigs Annalen der Chemie,1927,vol. 451,p. 285,302.
[3]Justus Liebigs Annalen der Chemie,1927,vol. 451,p. 285,302.

4
[ 101860-76-8 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 74209-34-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1927,vol. 451,p. 285,302.

5
[ 7726-95-6 ]
[ 64-19-7 ]
[ 2942-42-9 ]
[ 74209-34-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1927,vol. 451,p. 285,302.

6
[ 2942-42-9 ]
sodium hypobromite solution [ No CAS ]
[ 74209-34-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1927,vol. 451,p. 285,302.

7
[ 74209-34-0 ]
[ 316810-90-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2000,vol. 39,p. 339 - 345.
[2]Heterocycles,2000,vol. 53,p. 2617 - 2627.

8
[ 2942-42-9 ]
[ 74209-34-0 ]
[ 74209-35-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2000,vol. 39,p. 339 - 345.

9
[ 74209-34-0 ]
[ 64-17-5 ]
[ 98-68-0 ]
N-(3-bromo-1H-7-indazolyl)-4-methoxybenzenesulfonamide [ No CAS ]
N-(3-bromo-4-ethoxy-1H-7-indazolyl)-4-methoxybenzenesulfonamide [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 8218 - 8225.
[2]Synthetic Communications,2011,vol. 41,p. 999 - 1005.

10
[ 74209-34-0 ]
[ 74-88-4 ]
[ 74209-37-3 ]

References: [1]Tetrahedron,2005,vol. 61,p. 8218 - 8225.
[2]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 5962 - 5973.

11
[ 74209-34-0 ]
3-bromo-1-methyl-1H-indazol-7-ylamine [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 8218 - 8225.

12
[ 74209-34-0 ]
3-bromo-4-ethoxy-1-methyl-1H-indazol-7-ylamine [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 8218 - 8225.

13
[ 74209-34-0 ]
N-(3-bromo-4-ethoxy-1-methyl-1H-7-indazolyl)-4-methoxybenzenesulfonamide [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 8218 - 8225.

14
[ 74209-34-0 ]
1-bromo-4-butoxycarbonylmethylidene-3,7-dihydro-6-methylpyrazolo[1,5,4-ef][1,5]benzodiazepine [ No CAS ]

References: [1]Heterocycles,2000,vol. 53,p. 2617 - 2627.

15
[ 74209-34-0 ]
3-bromo-7-butoxycarbonylidene-1,9-dihydro-8-methylpyrazolo[4,5-h]quinoline [ No CAS ]

References: [1]Heterocycles,2000,vol. 53,p. 2617 - 2627.

16
[ 74209-34-0 ]
[ 316811-05-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2000,vol. 39,p. 339 - 345.

17
[ 74209-34-0 ]
2-bromo-6-ethyl-9-methyl-6H-1,6,9a-triaza-benzo[cd]azulen-7-one [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2000,vol. 39,p. 339 - 345.

18
[ 74209-34-0 ]
6-allyl-2-bromo-9-methyl-6H-1,6,9a-triaza-benzo[cd]azulen-7-one [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2000,vol. 39,p. 339 - 345.

19
[ 570-24-1 ]
[ 74209-34-0 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2000,vol. 39,p. 339 - 345.

20
[ 74209-34-0 ]
[ 74-88-4 ]
[ 74209-39-5 ]
[ 74209-37-3 ]

Yield	Reaction Conditions	Operation in experiment
44%; 37%	With sodium methylate; In methanol; for 48h;Reflux;	In a round-bottomed flask equipped with reflux condenser, <strong>[74209-34-0]3-bromo-7-nitro-1H-indazole</strong> (5) (0.63 g, 2.6 mmol) was dissolvedin dry methanol (25 mL). Then, sodium methoxyde (0.18 g,3.3 mmol) and 0.55 g of methyl iodide (0.24 mL, 3.9 mmol) wereadded. The mixture was heated to reflux for 2 days and then thesolvent was removed under reduced pressure. Water (30 mL)was added and the residue was extracted with chloroform(3 x 45 mL). The organic layers were combined, dried (Na2SO4),and concentrated to afford a crude solid formed mainly by thetwo isomers. After silica gel chromatography with (hexane/ethylacetate 30:1), 1 was obtained first (0.24, 37%) and increasing to1:1 to afford 2 (0.29, 44%).

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6180 - 6187.
[2]Journal of Molecular Structure,2011,vol. 985,p. 75 - 81.

21
[ 74209-34-0 ]
[ 24424-99-5 ]
[ 1260655-33-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dmap; triethylamine; In dichloromethane; at 20℃; for 16h;Reflux;	1003901 Step A: Preparation of tert-butyl 3-bromo-7-nitro- 1 H-indazole- 1 -carboxylate:To a solution of 3-bromo-7-nitro- 1 H-indazole (1.0 g, 4.13 mmol) in DCM (30 mL) were added Et3N (633 jiL, 4.54 mmol), DMAP (505 mg, 4.13 mmol) and Boc anhydride (992 mg, 4.54 mmol). The mixture was heated at reflux for 16 hours, cooled to ambient temperature and concentrated under vacuum. The residue was purified by silica column chromatography eluting with 9:1 hexanes / EtOAc, to afford tert-butyl 3-bromo-7-nitro-1fl-indazole-1-carboxylate (1.16 g, 82% yield) as a yellow solid. ?H NMR (CDC13) oe 8.08 (d, J 7.7 Hz, 1H), 7.93 (d, J 8.0 Hz, 1H), 7.50 (t, J 7.9 Hz, 1H), 1.65 (s, 9H) ppm.

References: [1]Patent: WO2014/78372,2014,A1 .Location in patent: Paragraph 00390.

22
[ 74209-34-0 ]
[ 24424-99-5 ]
[ 1610362-70-3 ]