1H-Indazole-5-carbaldehyde supplier

Name
1H-Indazole-5-carbaldehyde
EINECS
CAS No. 253801-04-6
Article Data19
CAS DataBase
Density 1.369 g/cm³
Solubility
Melting Point 115-119°C
Formula C₈H₆N₂O
Boiling Point 358.3 °C at 760 mmHg
Molecular Weight 146.148
Flash Point 174.4 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms ZINC08700340;
PSA 45.75000
LogP 1.37540

Synthetic route

: 5-hydroxymethyl-1H-indazole

: 253801-04-6
1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
With Dess-Martin periodane In dichloromethane for 12h;	100%
With Dess-Martin periodane In dichloromethane	82%
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h;	74%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate at 90℃; for 17h;
With Dess-Martin periodane In dichloromethane for 2h; Dess-Martin Oxidation;

: 201230-82-2
carbon monoxide

: 55919-82-9
5-iodo-1H-indazole

: 141-53-7
sodium formate

: 253801-04-6
1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 110℃; for 6h;	59%

...Expand

: 53857-57-1
5-bromo-1H-indazole

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 253801-04-6
1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
Stage #1: 5-bromo-1H-indazole With n-butyllithium In tetrahydrofuran at -50℃; for 2h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran for 0.5h;	58%
Stage #1: 5-bromo-1H-indazole With n-butyllithium In tetrahydrofuran; hexane at -50℃; for 2h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -50℃; for 0.5h; Inert atmosphere;	58%
Stage #1: 5-bromo-1H-indazole With n-butyllithium In tetrahydrofuran at -78 - -40℃; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃;	52%

: 53857-57-1
5-bromo-1H-indazole

: 253801-04-6
1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
Stage #1: 5-bromo-1H-indazole With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.25h; Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran; hexane at -40 - 20℃; for 1.5h;	57%
With hydrogenchloride; sodium hydroxide; sodium hydrogensulfite In tetrahydrofuran; N-methyl-acetamide; cyclohexane; water; ethyl acetate; mineral oil

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 253801-04-6
1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
Stage #1: 5-bromo-1H-indazole With n-butyllithium In tetrahydrofuran at -78 - -40℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃; for 2.5h; Stage #3: With water In tetrahydrofuran	52%

: trihydrogen phosphate

: 74626-47-4
1H-indazole-5-carbonitrile

: 253801-04-6
1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
With pyridine; aluminum nickel In water; acetic acid

: 88990-57-2
4-(Hydroxymethyl)-2-methylaniline

: 253801-04-6
1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium acetate / chloroform / 3 h / Reflux 2: isopentyl nitrite; 18-crown-6 ether / 24 h / Reflux 3: sodium hydroxide / methanol / 1 h 4: Dess-Martin periodane / dichloromethane / 2 h View Scheme

: C10H13NO2

: 253801-04-6
1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: isopentyl nitrite; 18-crown-6 ether / 24 h / Reflux 2: sodium hydroxide / methanol / 1 h 3: Dess-Martin periodane / dichloromethane / 2 h View Scheme

: acetic acid 1H-indazol-5-ylmethyl ester

: 253801-04-6
1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / 1 h 2: Dess-Martin periodane / dichloromethane / 2 h View Scheme

: 1619884-78-4
(E)-N-(5,6-dichloropyridin-3-yl)-1-(1H-indazol-5-yl)methanimine

A: 253801-04-6
1H-indazole-5-carbaldehyde

B: 98121-41-6
5-Amino-2,3-dichloropyridine

Conditions

Conditions	Yield
In methanol at 20℃; for 1488h;

: 253801-04-6
1H-indazole-5-carbaldehyde

: 24424-99-5
di-tert-butyl dicarbonate

: 635713-71-2
tert-butyl 5-formyl-1H-indazole-1-carboxylate

Conditions

Conditions	Yield
dmap In acetonitrile at 20℃; for 0.5h;	99%
With dmap; triethylamine In dichloromethane	90%
With dmap; triethylamine In dichloromethane at 20℃; for 16h;	90%
With dmap; triethylamine In dichloromethane at 20℃; for 16h;	90%
With dmap; triethylamine In dichloromethane at 20℃; for 16h;	90%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 1086391-03-8
3-chloro-1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
With N-chloro-succinimide In acetonitrile at 20℃; for 12h; Reflux;	97%
With N-chloro-succinimide In acetonitrile at 65 - 70℃; for 50h;	54%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 95-76-1
m,p-dichloroaniline

: 1619884-75-1
(E)-N-(3,4-dichlorophenyl)-1-(1H-indazol-5-yl)methanimine

Conditions

Conditions	Yield
With acetic acid In ethanol Reflux;	90%
With acetic acid In ethanol pH=4 - 5; Reflux;	90%
With acetic acid In ethanol for 0.5h; Reflux;	89%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 121056-95-9
trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate

: C16H19N3O4

Conditions

Conditions	Yield
Stage #1: trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate With N,N,N',N'-tetramethylguanidine In tetrahydrofuran at -70℃; for 0.0833333h; Stage #2: 1H-indazole-5-carbaldehyde In tetrahydrofuran at -70 - 80℃;	87%
Stage #1: trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate With N,N,N',N'-tetramethylguanidine In tetrahydrofuran at -70 - 80℃; for 16h; Stage #2: 1H-indazole-5-carbaldehyde In tetrahydrofuran at 80℃; for 16h;	87%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 98-09-9
benzenesulfonyl chloride

: 1-(phenylsulfonyl)-1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;	83%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 1086391-08-3
3-bromo-1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 20 - 34.9℃; for 4.08333h;	82%
With N-Bromosuccinimide In acetonitrile at 20℃; for 0.833333h; Reflux;	75%
With N-Bromosuccinimide at 0 - 20℃;	70.9%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 5-hydroxymethyl-1H-indazole

Conditions

Conditions	Yield
With tricobalt tetraoxide In isopropyl alcohol at 50℃; for 0.5h; Green chemistry; chemoselective reaction;	79%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 128-08-5
N-Bromosuccinimide

: 1086391-08-3
3-bromo-1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 0.833333h; Reflux;	75%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 106-65-0
Dimethyl succinate

: 635713-14-3
2-[1-(1H-indazol-5-yl)methylidene]succinic acid 1-methyl ester

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 60℃; for 2h;	74%
With potassium tert-butylate In tert-butyl alcohol Stobbe condensation;

: 253801-04-6
1H-indazole-5-carbaldehyde

: 944899-01-8
3-iodo-5-formyl-1H-indazole

Conditions

Conditions	Yield
With iodine; sodium hydroxide In 1,4-dioxane; water at 20℃; for 2h;	72%
With iodine; sodium hydroxide In 1,4-dioxane; water at 20℃; for 2h;	72%
With sodium hydroxide; iodine In 1,4-dioxane; water at 20℃; for 2h;	64.5%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 106018-85-3
2-trimethylsilanyl-ethanesulfonyl chloride

: 635713-79-0
1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 18h;	71%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 119072-55-8, 7188-38-7
tert-butylisonitrile

: N-tert-butyl tetrazolo-5-α,α-dimethyl methylamine

: N-(tert-butyl)-2-((2-(1-(tert-butyl)-1H-tetrazol-5-yl)propan-2-yl)amino)-2-(1H-indazol-5-yl)acetamide

Conditions

Conditions	Yield
With p-toluene sulfinic acid In methanol at 20℃; for 18h; Ugi Condensation;	71%

...Expand

: 253801-04-6
1H-indazole-5-carbaldehyde

: 3-morpholine-N-(2-oxindolin-5-yl)propionamide

: N-(3-((1H-indazol-5-yl)methylene)-2-oxoindolin-5-yl)-3-morpholinopropanamide

Conditions

Conditions	Yield
With piperidine In ethanol for 12h; Knoevenagel Condensation; Reflux;	71%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 367-21-5
3-chloro-4-fluorophenylamine

: 1619884-77-3
(E)-N-(3-chloro-4-fluorophenyl)-1-(1H-indazol-5-yl)methanimine

Conditions

Conditions	Yield
With acetic acid In ethanol pH=4 - 5; Reflux;	69%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 83-72-7
2-Hydroxy-1,4-naphthoquinone

: 2-hydroxy-3-[(indazol-5-yl)methyl]-1,4-naphthoquinone

Conditions

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; L-proline In dichloromethane for 18h; Reflux; Inert atmosphere;	66%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 19335-11-6
1H-indazol-5-ylamine

: 108-94-1
cyclohexanone

: 7-(1H-indazol-5-yl)-8,9,10,11-tetrahydro-3H-pyrazolo[4,3-a]phenanthridine

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 12h; Reflux;	65%

...Expand

: 253801-04-6
1H-indazole-5-carbaldehyde

: 98121-41-6
5-Amino-2,3-dichloropyridine

: 1619884-78-4
(E)-N-(5,6-dichloropyridin-3-yl)-1-(1H-indazol-5-yl)methanimine

Conditions

Conditions	Yield
With acetic acid In ethanol pH=4 - 5; Reflux;	65%

: 253801-04-6
1H-indazole-5-carbaldehyde

: N-(2-oxoindolin-5-yl)morpholine-4-carboxamide

: N-(3-((1H-indazol-5-yl)methylene)-2-oxoindolin-5-yl)morpholine-4-carboxamide

Conditions

Conditions	Yield
With piperidine In ethanol for 12h; Knoevenagel Condensation; Reflux;	65%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 100-58-3
phenylmagnesium bromide

: 1025762-64-4
(1H-indazol-5-yl)(phenyl)methanol

Conditions

Conditions	Yield
Stage #1: 1H-indazole-5-carbaldehyde; phenylmagnesium bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran for 72h; Stage #2: With water In tetrahydrofuran	64%
Stage #1: 1H-indazole-5-carbaldehyde; phenylmagnesium bromide With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran for 36h; Stage #2: With methanol In tetrahydrofuran	64%

: 253801-04-6
1H-indazole-5-carbaldehyde

: N-(2-oxoindolin-5-yl)-3-(piperidin-1-yl)propionamide

: N-(3-((1H-indazol-5-yl)methylene)-2-oxoindolin-5-yl)-3-(piperidin-1-yl)propanamide

Conditions

Conditions	Yield
With piperidine In ethanol for 12h; Knoevenagel Condensation; Reflux;	63%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 6482-24-2
2-Bromoethyl methyl ether

A: 1-(2-methoxyethyl)-1H-indazole-5-carbaldehyde

B: 2-(2-methoxyethyl)-2H-indazole-5-carbaldehyde

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 95℃; for 72h;	A 59% B 30%

...Expand

: 253801-04-6
1H-indazole-5-carbaldehyde

: 367-22-6
4-chloro-3-fluoroaniline

: 1619884-76-2
(E)-N-(4-chloro-3-fluorophenyl)-1-(1H-indazol-5-yl)methanimine

Conditions

Conditions	Yield
With acetic acid In ethanol pH=4 - 5; Reflux;	58%

: 253801-04-6
1H-indazole-5-carbaldehyde

: diphenyl (6-methylpyridin-2-yl)anilinomethylphosphate

: 2-(1H-indazol-5-yl)-1-(6-methylpyridin-2-yl)ethanone

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran; isopropyl alcohol at 20℃; for 12h;	58%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 614750-85-5
diphenyl (6-methylpyridin-2-yl)(phenylamino)methylphosphonate

: 2-(1H-indazol-5-yl)-1-(6-methylpyridin-2-yl)ethanone

Conditions

Conditions	Yield
Stage #1: 1H-indazole-5-carbaldehyde; diphenyl (6-methylpyridin-2-yl)(phenylamino)methylphosphonate With caesium carbonate In tetrahydrofuran; isopropyl alcohol at 20℃; for 12h; Stage #2: With hydrogenchloride In tetrahydrofuran; water; isopropyl alcohol	58%

: 253801-04-6
1H-indazole-5-carbaldehyde

: 5192-03-0
5-amino-1H-indole

: 108-94-1
cyclohexanone

: 7-(1H-indazol-5-yl)-8,9,10,11-tetrahydro-3H-pyrrolo[3,2-a]phenanthridine

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 12h; Reflux;	51%

...Expand

1H-Indazole-5-carbaldehyde Specification

This chemical also known as ZINC08700340 is an organic compound with the formula C₈H₆N₂O. It belongs to the product categories of Aldehyde; Building Blocks; Indazole. With the CAS registry number 253801-04-6, its IUPAC name is 1H-indazole-5-carbaldehyde.

Physical properties of 1H-Indazole-5-carbaldehyde: (1)ACD/LogP: 1.24; (2)ACD/LogD (pH 5.5): 1.24; (3)ACD/LogD (pH 7.4): 1.24; (4)ACD/BCF (pH 5.5): 5.17; (5)ACD/BCF (pH 7.4): 5.17; (6)ACD/KOC (pH 5.5): 112.84; (7)ACD/KOC (pH 7.4): 112.84; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.747; (12)Molar Refractivity: 43.37 cm³; (13)Molar Volume: 106.7 cm³; (14)Surface Tension: 71 dyne/cm; (15)Density: 1.368 g/cm³; (16)Flash Point: 174.4 °C; (17)Enthalpy of Vaporization: 60.38 kJ/mol; (18)Boiling Point: 358.3 °C at 760 mmHg; (19)Vapour Pressure: 2.56E-05 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC2=C(C=C1C=O)C=NN2
(2)InChI: InChI=1S/C8H6N2O/c11-5-6-1-2-8-7(3-6)4-9-10-8/h1-5H,(H,9,10)
(3)InChIKey: YJKMYHNMBGQQQZ-UHFFFAOYSA-N

Product Name

1H-Indazole-5-carbaldehyde

Synthetic route

1H-Indazole-5-carbaldehyde Specification

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