53857-57-1

Basic information

• Product Name: 5-Bromoindazole
• Synonyms: 5-Bromo-1H-indazole 97%;5-Bromo-1H-indazole ,98%;1H-Indazole, 5-bromo-;5-BroMo-1H-indazole, 97+%;5-Bromoindazole-2;5-BROMO-1H-INDAZOLE;5-BROMOINDAZOLE;4-BROMOIMIDAZOLE
• CAS NO: 53857-57-1
• Molecular Formula: C₇H₅BrN₂
• Molecular Weight: 197.03
• Product Categories: pharmacetical;Halides;Fused Ring Systems;Halogenated Heterocycles;Heterocyclic Building Blocks;Indazoles;Building Blocks;Indazole
• Mol File: 53857-57-1.mol
• Article Data: 37

Chemical Properties

• Melting Point: 131-135 °C(lit.)
• Boiling Point: 333.821 °C at 760 mmHg
• Flash Point: 155.69 °C
• Appearance: /
• Density: 1.771 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.728
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 12.74±0.40(Predicted)
• CAS DataBase Reference: 5-Bromoindazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromoindazole(53857-57-1)
• EPA Substance Registry System: 5-Bromoindazole(53857-57-1)

Safety Data

• Hazard Codes: T,Xn
• Statements: 25-36/37/38-22-41
• Safety Statements: 26-36-36/37/39-22-39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: NI3517450
• Hazardous Substances Data: 53857-57-1(Hazardous Substances Data)

Usage

Chemical Properties

White to light brown solid

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

Synthetic route

tert-butyl (4-bromo-2-methylphenyl)azo sulfide → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide for 1.5h; Ambient temperature;	98%

5-bromo-2-fluorobenzaldehyde (93777-26-5) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With hydrazine hydrate at 100℃; for 12h;	96%
With hydrazine at 100℃;	50%
With hydrazine hydrate In 1,2-dimethoxyethane for 15h; Heating;	45%

4-Bromo-2-methylaniline (583-75-5) + isopentyl nitrite (110-46-3) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; potassium acetate; acetic anhydride In n-heptane; chloroform; water; ethyl acetate	94%

5-bromo-1-(phenylsulfonyl)-1H-indazole → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; Cu(dq)((rac)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene)BF4; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Irradiation;	89%

3,5-dibromoindazole (40598-76-3) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With methanol; magnesium at 20℃; chemoselective reaction;	84%
With phosphorus; hydrogen iodide at 110℃;

5-bromo-1-tosyl-1H-indazole → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With sodium hydride In N,N-dimethyl acetamide at 60℃; for 2h; Inert atmosphere;	82%

4-bromo-2-methylbenzenediazonium tetrafluoroborate → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With 18-crown-6 ether; potassium acetate In chloroform at 20℃; for 2h;	80%
With potassium acetate; 18-crown-6 ether In chloroform at 20℃; for 2h;	65%
With 18-crown-6 ether; potassium acetate In chloroform at 20℃;	60%

4-Bromo-2-methylaniline (583-75-5) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With acetic acid; sodium nitrite In water at 20℃; for 5h;	61%
Stage #1: 4-Bromo-2-methylaniline With acetic anhydride In chloroform at 0 - 40℃; for 1h; Stage #2: With potassium acetate; isopentyl nitrite In chloroform for 18h; Heating / reflux; Stage #3: With hydrogenchloride In water at 50℃; for 2h;	60%
Stage #1: 4-Bromo-2-methylaniline With tetrafluoroboric acid; sodium nitrite In water at 0℃; Stage #2: With 18-crown-6 ether; potassium acetate In chloroform at 20℃; Further stages.;
Multi-step reaction with 2 steps 1.1: water / 0.25 h / 20 °C 1.2: 0 - 5 °C 2.1: 18-crown-6 ether; potassium acetate / chloroform / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium acetate / toluene / 0.67 h / 85 °C 2: toluene / 4.25 h / 65 °C View Scheme

3-amino-5-bromo-1H-indazole (61272-71-7) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With nitrous acid isobutyl ester; hypophosphorous acid In ethanol; water at 0 - 20℃; for 3h;	40%

5-bromobenzopyrazole-3-carboxylic acid (1077-94-7) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
at 320℃;

3-Diazo-3H-indazol (2596-89-6) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With hydrogen bromide

acetic acid-(4-bromo-2-methyl-N-nitroso-anilide) (861796-22-7) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With benzene

acetic acid-(4-bromo-2-methyl-N-nitroso-anilide) (861796-22-7) + benzene (71-43-2) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
at 60℃;

5-bromo-indazole-carboxylic acid-(3) → 5-bromo-1H-indazole (53857-57-1)

5-bromo-1-(2-nitro-benzoyl)-1H-indazole + alcoholic KOH-solution → 5-bromo-1H-indazole (53857-57-1)

hydrogen iodide (10034-85-2) + 3,5-dibromoindazole (40598-76-3) + red phosphorus → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
at 110℃;

5-bromobenzopyrazole-3-carboxylic acid (1077-94-7) + water (7732-18-5) → 5-bromo-1H-indazole (53857-57-1) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5)

Conditions	Yield
at 200℃;

3-Diazo-3H-indazol (2596-89-6) + hydrogen bromide (10035-10-6, 12258-64-9) → benzimidazole (271-44-3) + 5-bromo-1H-indazole (53857-57-1) + 3-bromo-1H-indazole (40598-94-5) + 3,5-dibromoindazole (40598-76-3)

5-bromo-2-fluoro-benzaldehyde O-methyl-oxime → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With hydrazine In 1,2-dimethoxyethane Heating;
With hydrazine hydrate Reflux;
With hydrazine hydrate Reflux;

tert.-butylnitrite (540-80-7) + 4'-bromo-2'-methylacetanilide (24106-05-6) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
In toluene at 65℃; for 4.25h;

4'-bromo-2'-methylacetanilide (24106-05-6) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: glacial acetic acid / Einleiten von nitrosen Gasen 2: benzene View Scheme
Multi-step reaction with 3 steps 1.1: hydrogenchloride / ethanol / 3 h / Reflux 1.2: 0.5 h / 20 °C 2.1: water / 0.25 h / 20 °C 2.2: 0 - 5 °C 3.1: 18-crown-6 ether; potassium acetate / chloroform / 2 h / 20 °C View Scheme

3-bromo-1H-indazole (40598-94-5) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: glacial acetic acid / durch Bromierung 2: concentrated hydriodic acid; red phosphorus / 110 °C View Scheme

aqueous concentrated HCl + ammonium tetrafluroborate (13826-83-0) + 4-Bromo-2-methylaniline (583-75-5) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With potassium acetate; sodium nitrite In chloroform; acetic acid
With potassium acetate; sodium nitrite In chloroform; acetic acid
With potassium acetate; sodium nitrite In chloroform; acetic acid

ammonium tetrafluroborate (13826-83-0) + 4-Bromo-2-methylaniline (583-75-5) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With hydrogenchloride; potassium acetate; acetic acid; sodium nitrite In chloroform; water

5-bromo-2-fluorobenzaldehyde (93777-26-5) → 5-bromo-2-fluorotoluene (51437-00-4) + 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
With hydrazine Inert atmosphere; Reflux;

o-toluidine (95-53-4) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 2 h / 110 - 115 °C 2.1: bromine; acetic acid / 1.5 h / 50 °C 3.1: hydrogenchloride / ethanol / 3 h / Reflux 3.2: 0.5 h / 20 °C 4.1: water / 0.25 h / 20 °C 4.2: 0 - 5 °C 5.1: 18-crown-6 ether; potassium acetate / chloroform / 2 h / 20 °C View Scheme

N-(2-methylphenyl)acetamide (120-66-1) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: bromine; acetic acid / 1.5 h / 50 °C 2.1: hydrogenchloride / ethanol / 3 h / Reflux 2.2: 0.5 h / 20 °C 3.1: water / 0.25 h / 20 °C 3.2: 0 - 5 °C 4.1: 18-crown-6 ether; potassium acetate / chloroform / 2 h / 20 °C View Scheme

N-methoxylamine hydrochloride (593-56-6) + 5-bromo-2-fluorobenzaldehyde (93777-26-5) → 5-bromo-1H-indazole (53857-57-1)

Conditions	Yield
Stage #1: N-methoxylamine hydrochloride; 5-bromo-2-fluorobenzaldehyde With potassium carbonate In 1,2-dimethoxyethane at 40℃; Stage #2: With hydrazine In 1,2-dimethoxyethane Reflux;

5-bromo-1H-indazole (53857-57-1) → 5-bromo-3-iodo-1H-indazole (459133-66-5)

Conditions	Yield
With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3h;	100%
Stage #1: 5-bromo-1H-indazole With potassium tert-butylate In tetrahydrofuran at 0℃; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃;	99%
With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	97.9%

di-tert-butyl dicarbonate (24424-99-5) + 5-bromo-1H-indazole (53857-57-1) → tert-butyl 5-bromo-1H-indazole-1-carboxylate (651780-02-8)

Conditions	Yield
With dmap In dichloromethane at 20℃;	100%
With dmap; triethylamine In acetonitrile for 3h;	99%
With dmap In acetonitrile at 23℃; for 0.25h; Inert atmosphere;	99%

5-bromo-1H-indazole (53857-57-1) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (862723-42-0)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 100℃; Inert atmosphere;	100%
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 90℃; for 24h;	84%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 24h; Inert atmosphere;	81%

5-bromo-1H-indazole (53857-57-1) → 5-iodo-1H-indazole (55919-82-9)

Conditions	Yield
With sodium iodide; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide In 1,4-dioxane at 110℃; for 68h;	100%

5-bromo-1H-indazole (53857-57-1) + ethyl vinyl ether (109-92-2) → 5-bromo-1-(1-ethoxyethyl)-1H-indazole (1178903-22-4)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane for 18h; regioselective reaction;	99%

5-bromo-1H-indazole (53857-57-1) + N,2-dimethylaniline (611-21-2) → N-methyl-N-(o-tolyl)-1H-indazol-5-amine (1248590-76-2)

Conditions	Yield
With chloro-(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II); lithium hexamethyldisilazane; ruphos In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Sealed vial;	99%
With [Pd(RuPhos)(dvtms)]; lithium hexamethyldisilazane In tetrahydrofuran at 65℃; for 16h; Buchwald-Hartwig Coupling; Sealed tube;

3,4-dihydro-2H-pyran (110-87-2) + 5-bromo-1H-indazole (53857-57-1) → 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane for 1h; regioselective reaction;	98.2%
With toluene-4-sulfonic acid In toluene at 15 - 75℃; for 2h; Inert atmosphere;	98%
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 3h;	97%

5-bromo-1H-indazole (53857-57-1) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (894808-05-0)

Conditions	Yield
Stage #1: 5-bromo-1H-indazole With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 20℃; for 16h;	98%
With potassium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 0 - 20℃; for 3h;	81%
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water for 3h; Inert atmosphere;	81%
Stage #1: 5-bromo-1H-indazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 20℃; for 3h;	70%
Stage #1: 5-bromo-1H-indazole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide at 0℃; for 2h;	63%

5-bromo-1H-indazole (53857-57-1) + 1-(4-chlorophenyl)piperazine hydrochloride (13078-12-1) → 5-(4-(4-chlorophenyl)piperazin-1-yl)-1H-indazole (1248590-77-3)

Conditions	Yield
With RuPhos palladacycle; lithium hexamethyldisilazane; ruphos In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Sealed vial;	98%

5-bromo-1H-indazole (53857-57-1) + p-toluenesulfonyl chloride (98-59-9) → 5-bromo-1-tosyl-1H-indazole

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 50℃; Reagent/catalyst; Temperature;	97%
With triethylamine In acetonitrile at 50℃; for 8h;	93%

3-Dimethylaminopropanethiol (42302-17-0) + 5-bromo-1H-indazole (53857-57-1) → 3-((1H-indazol-5-yl)thio)-N,N-dimethylpropan-1-amine

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at 120℃; for 16h; Inert atmosphere;	97%

5-bromo-1H-indazole (53857-57-1) + dimethyl amine (124-40-3) → N,N-dimethyl-1H-indazol-5-amine

Conditions	Yield
With RuPhos palladacycle; lithium hexamethyldisilazane; ruphos In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Sealed vial;	96%

5-bromo-1H-indazole (53857-57-1) + phenylboronic acid (98-80-6) → 5-bromo-1-phenyl-1H-indazole (861905-18-2)

Conditions	Yield
With pyridine; oxygen; copper diacetate In dichloromethane at 15℃; for 12h;	96%

5-bromo-1H-indazole (53857-57-1) + Acetic formic anhydride (2258-42-6) → 1H-indazole-5-carboxylic acid (61700-61-6)

Conditions	Yield
Stage #1: 5-bromo-1H-indazole; formyl acetic anhydride With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water pH=Ca. 4 - 6;	95%

3-mercaptopropionic acid ethyl ester (5466-06-8) + 5-bromo-1H-indazole (53857-57-1) → ethyl 3-((1H-indazol-5-yl)thio)propionate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 2h; Inert atmosphere;	95%

5-bromo-1H-indazole (53857-57-1) + [2-(2-fluorophenyl)ethyl]amine (52721-69-4) → N-(2-fluorophenethyl)-1H-indazol-5-amine (1248590-86-4)

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); lithium hexamethyldisilazane In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Sealed vial;	94%

3-methoxybenzenethiol (15570-12-4) + 5-bromo-1H-indazole (53857-57-1) → C14H12N2OS

Conditions	Yield
With C31H49O2P*C12H10N(1-)*CH3O3S(1-)*Pd(2+)*CH2Cl2; lithium hexamethyldisilazane In tetrahydrofuran at 20℃;	93%

5-bromo-1H-indazole (53857-57-1) + acetic anhydride (108-24-7) → 1-(5-bromo-1H-indazol-1-yl)ethanone (152626-92-1)

Conditions	Yield
for 2h; Reflux;	92%
Stage #1: 5-bromo-1H-indazole With ferrocene; tert-butylammonium hexafluorophosphate(V) In acetonitrile at 20℃; for 3h; Electrochemical reaction; Inert atmosphere; Glovebox; Stage #2: acetic anhydride In acetonitrile for 2h; Electrochemical reaction; Inert atmosphere; Glovebox;	72%
With pyridine; dmap In dichloromethane at 40℃;	70%

5-bromo-1H-indazole (53857-57-1) + benzyl bromide (100-39-0) → 2-benzyl-5-bromo-2H-indazole (937049-51-9) + 1-benzyl-5-bromo-1H-indazole (1087160-01-7)

Conditions	Yield
Stage #1: 5-bromo-1H-indazole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	A 88% B 92%
With tetra-(n-butyl)ammonium iodide; sodium hydroxide In para-xylene at 130℃;	A 302 mg B 364 mg

5-bromo-1H-indazole (53857-57-1) + methyl iodide (74-88-4) → ClO4(1-)*C9H10BrN2(1+)

Conditions	Yield
Stage #1: 5-bromo-1H-indazole; methyl iodide With sodium hydroxide In methanol at 100℃; Sealed tube; Stage #2: With perchloric acid In water at 20℃;	92%

5-bromo-1H-indazole (53857-57-1) + phenylmethanethiol (100-53-8) → 5-(benzylthio)-1H-indazole

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 4h; Inert atmosphere;	92%
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; for 4h; Inert atmosphere;	92%

3,4-dihydro-2H-pyran (110-87-2) + 5-bromo-1H-indazole (53857-57-1) → 5-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole (1178903-21-3)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane for 5h; regioselective reaction;	91.8%

5-bromo-1H-indazole (53857-57-1) + 4-isoquinolineboronic acid (192182-56-2) → C16H11N3 (1610790-51-6)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tripotassium phosphate "n" hydrate; XPhos In butan-1-ol at 100℃; for 18h; Inert atmosphere;	91.1%
With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water Suzuki Coupling;

5-bromo-1H-indazole (53857-57-1) → 5-bromo-3-chloro-1H-indazole (36760-19-7)

Conditions	Yield
With N-chloro-succinimide; 2,4,6-trimethylaniline In acetonitrile at 20℃; for 24h; Inert atmosphere;	91%
With 1-chloro-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one In N,N-dimethyl-formamide at 20℃; for 12h; regioselective reaction;	86%
With N-chloro-succinimide In acetonitrile at 65℃; for 3h;	48.7%

zinc(II) cyanide (557-21-1) + 5-bromo-1H-indazole (53857-57-1) → 1H-indazole-5-carbonitrile (74626-47-4)

Conditions	Yield
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(dibenzylideneacetone)-palladium(0) In water; N,N-dimethyl-formamide at 150℃; for 0.75h; Sealed vial;	91%
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In water; N,N-dimethyl-formamide at 150℃; for 1.5h; Inert atmosphere; Microwave irradiation;	24%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 5-bromo-1H-indazole (53857-57-1) → 1H-indazole-5-carboxylic acid (61700-61-6)

Conditions	Yield
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; palladium dichloride In acetonitrile at 100℃; under 30003 Torr; for 18h;	90%

5-bromo-1H-indazole (53857-57-1) → 5-bromo-4-nitro-1H-indazole

Conditions	Yield
With sulfuric acid; nitric acid In water at 0℃; for 1h;	90%

Upstream product

• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 593-56-6 N-methoxylamine hydrochloride 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 95-53-4 o-toluidine 
• 61272-71-7 3-amino-5-bromo-1H-indazole 
• 13826-83-0 ammonium tetrafluroborate 
• 583-75-5 4-Bromo-2-methylaniline 
• 110-46-3 isopentyl nitrite 
• 40598-94-5 3-bromo-1H-indazole 
• 24106-05-6 4'-bromo-2'-methylacetanilide 
• 540-80-7 tert.-butylnitrite 
• 914311-53-8 5-bromo-2-fluoro-benzaldehyde O-methyl-oxime 
• 2596-89-6 3-Diazo-3H-indazol 
• 10035-10-6 hydrogen bromide 

Downstream Products

• 40598-76-3 3,5-dibromoindazole 
• 552331-32-5 5-bromo-3-(N,N-dimethylamino)-1H-indazole 
• 862723-42-0 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 
• 465529-56-0 2-Methyl-5-bromo-2H-indazole 
• 1178903-30-4 1-(bis(4-methoxyphenyl)(phenyl)methyl)-5-bromo-1H-indazole 
• 937049-51-9 5-bromo-2-benzyl-2H-indazole 
• 1035096-84-4 5-bromo-2-(4-methoxybenzyl)-2H-indazole 
• 1087160-01-7 5-bromo-1-benzyl-1H-indazole 
• 1035096-83-3 5-bromo-1-(4-methoxybenzyl)-1H-indazole 
• 1185767-44-5 2H-indazole-5-carbaldehyde 
• 1211537-09-5 5-bromo-3-fluoro-1H-indazole 
• 1082525-64-1 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 
• 465529-57-1 5-bromo-1-methyl-1H-indazole 

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