4-Nitroindole supplier | CasNO.4769-97-5

Name
4-Nitroindole
EINECS
CAS No. 4769-97-5
Article Data31
CAS DataBase
Density 1.425 g/cm³
Solubility
Melting Point 203-207 ºC
Formula C₈H₆N₂O₂
Boiling Point 362.6 ºC at 760 mmHg
Molecular Weight 162.148
Flash Point 173.1 ºC
Transport Information
Appearance Yellow Crystalline Solid
Safety 36/37-45
Risk Codes 68
Molecular Structure
Hazard Symbols Xn
Synonyms 4-nitro-1H-indole;Indole, 4-nitro-;1H-Indole, 4-nitro-;4-Nitro indole;
PSA 61.61000
LogP 2.59930

Synthetic route

: 4769-97-5
4-nitro-1H-indoIe

: 10553-11-4
4-nitro-1H-indole-3-carbaldehyde

: 4769-97-5
4-nitro-1H-indoIe

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 1.5h; Heating;	99%

: 81038-27-9
methyl 2-hydroxy-2-(4-nitroindol-1-yl)-acetate

: 4769-97-5
4-nitro-1H-indoIe

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; water for 0.0833333h; Heating;	94.5%

: 81038-26-8
methyl 2-(4-nitroindole-1-yl)oxyacetate

: 4769-97-5
4-nitro-1H-indoIe

Conditions

Conditions	Yield
With triethylamine In methanol for 16h; Ambient temperature;	94.3%

: 195992-08-6
2,6-dinitrostyrene

: 4769-97-5
4-nitro-1H-indoIe

Conditions

Conditions	Yield
With triphenylphosphine; palladium diacetate In acetonitrile under 3040 Torr; for 26h; Heating;	89%
With carbon monoxide; palladium diacetate; triphenylphosphine In acetonitrile at 90℃; under 3051.25 Torr; for 50h;	89%

: 10553-11-4
4-nitro-1H-indole-3-carbaldehyde

: 143-33-9
sodium cyanide

A: 4769-97-5
4-nitro-1H-indoIe

B: 4770-06-3
4-nitro-3-indoleacetonitrile

C: N-(4-nitroindol-3-yl)methylformamide

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol; formamide at 100℃; for 5h;	A 2% B 88% C 9%

...Expand

: 78283-23-5
1-hydroxy-4-nitroindole

: 105-36-2
ethyl bromoacetate

A: 4769-97-5
4-nitro-1H-indoIe

B: 81038-27-9
methyl 2-hydroxy-2-(4-nitroindol-1-yl)-acetate

C: 81038-26-8
methyl 2-(4-nitroindole-1-yl)oxyacetate

Conditions

Conditions	Yield
With triethylamine In methanol for 43h; Ambient temperature;	A 59.2% B 20% C 14.4%
With triethylamine In methanol Product distribution; Ambient temperature; different reaction time;

...Expand

: 78283-21-3
3-nitro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene

A: 5192-23-4
4-amino-1H-indole

B: 4769-97-5
4-nitro-1H-indoIe

C: 78283-23-5
1-hydroxy-4-nitroindole

D: 78283-24-6
1-hydroxy-4-nitrooxyindole

Conditions

Conditions	Yield
With titanium(III) chloride In water; acetic acid for 0.116667h; Ambient temperature;	A 2.8% B 13.1% C 56.8% D 15.9%
With titanium(III) chloride In methanol for 0.116667h; Ambient temperature;	A 3.6% B 31.3% C 47.3% D 5.6%
With titanium(III) chloride In N,N-dimethyl-formamide for 0.116667h; Product distribution; Ambient temperature; investigation of the synthesis and stability of the 4-substituted 1-hydroxy-indoles;	A 41.8% B 6.3% C 21.9% D 1.3%

...Expand

: 151-50-8
potassium cyanide

: 7150-46-1
4-nitrogramine

A: 4769-97-5
4-nitro-1H-indoIe

B: 4770-06-3
4-nitro-3-indoleacetonitrile

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide for 1.5h; Heating;	A 9.9% B 55.9%
In water; N,N-dimethyl-formamide for 2h; Heating;	A 24.6% B 50.7%

...Expand

: 4769-95-3
1-(4-nitro-1H-indol-3-yl)ethan-1-one

: 4769-97-5
4-nitro-1H-indoIe

Conditions

Conditions	Yield
With palladium diacetate; trifluoroacetic acid at 100℃; for 4h;	52%

: 78283-23-5
1-hydroxy-4-nitroindole

: 105-36-2
ethyl bromoacetate

A: 4769-97-5
4-nitro-1H-indoIe

B: 81038-26-8
methyl 2-(4-nitroindole-1-yl)oxyacetate

Conditions

Conditions	Yield
With triethylamine In methanol for 16h; Ambient temperature;	A 40.7% B 50.8%

...Expand

: 5192-23-4
4-amino-1H-indole

A: 4769-97-5
4-nitro-1H-indoIe

B: 135531-91-8
7-hydroxy-4-nitroindole

C: 135531-89-4
5-hydroxy-4-nitroindole

Conditions

Conditions	Yield
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetone for 0.583333h; pH 9;	A 32% B 5% C 16%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetone for 0.166667h; pH 9;	A 28% B 3% C 20%

...Expand

: 115118-93-9
ethyl N-(2-methyl-3-nitrophenyl)formimidate

: 95-92-1
oxalic acid diethyl ester

A: 4769-97-5
4-nitro-1H-indoIe

B: 90947-20-9
(4-nitroindol-3-yl)-2-oxoacetic acid

C: 91974-30-0
ethyl (4-nitroindol-3-yl)-2-oxoacetate

D: 115118-95-1
methyl (4-nitroindol-3-yl)-2-oxoacetate

Conditions

Conditions	Yield
With potassium ethoxide In diethyl ether; ethanol Heating; Title compound not separated from byproducts;	A 10% B 30% C n/a D n/a

...Expand

: 78283-21-3
3-nitro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene

A: 4769-97-5
4-nitro-1H-indoIe

B: 78283-23-5
1-hydroxy-4-nitroindole

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 1h;	A 9% B 27%

: 5192-23-4
4-amino-1H-indole

A: 4769-97-5
4-nitro-1H-indoIe

B: 4-nitrosoindole

C: 135531-89-4
5-hydroxy-4-nitroindole

Conditions

Conditions	Yield
With phosphate buffer; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetone for 0.583333h; Product distribution; various reagents, additives (pH), solvents and times;	A 15% B 21% C 14%
With phosphate buffer; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetone for 0.583333h; pH 7;	A 15% B 21% C 14%

...Expand

: 16732-60-8
4-nitro-1H-indole-2-carboxylic acid

: 4769-97-5
4-nitro-1H-indoIe

Conditions

Conditions	Yield
With quinoline; copper(II) oxide

: 67-56-1
methanol

: 10553-11-4
4-nitro-1H-indole-3-carbaldehyde

A: 4769-97-5
4-nitro-1H-indoIe

B: 4770-06-3
4-nitro-3-indoleacetonitrile

C: 3-methoxymethyl-4-nitroindole

Conditions

Conditions	Yield
With sodium tetrahydroborate; sodium cyanide 1.) 18 deg C, 1 h, 2.) reflux, 5 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 67-56-1
methanol

: 23099-33-4
4-nitrogramine methiodide

A: 4769-97-5
4-nitro-1H-indoIe

B: 3-methoxymethyl-4-nitroindole

C: 4-nitrobrassinin

D: methyl (4-nitroindol-3-ylmethyl)dithiocarbamate

Conditions

Conditions	Yield
With pyridine; carbon disulfide; ammonium hydroxide; triethylamine; methyl iodide Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 10553-11-4
4-nitro-1H-indole-3-carbaldehyde

: 143-33-9
sodium cyanide

A: 4769-97-5
4-nitro-1H-indoIe

B: 4770-06-3
4-nitro-3-indoleacetonitrile

C: 3-methoxymethyl-4-nitroindole

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate 1.) 18 deg C, 1 h, 2.) reflux, 5 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 23099-33-4
4-nitrogramine methiodide

A: 4769-97-5
4-nitro-1H-indoIe

B: 4-nitroindole-3-methanamine

C: 3-methoxymethyl-4-nitroindole

D: bis(4-nitroindol-3-ylmethyl)amine

Conditions

Conditions	Yield
With methanol; ammonium hydroxide for 2h; Heating; Yield given. Yields of byproduct given;

...Expand

: 23622-32-4
acetaldehyde-(3-nitro-phenylhydrazone)

A: 4769-96-4
6-nitroindole

B: 4769-97-5
4-nitro-1H-indoIe

Conditions

Conditions	Yield
GIPKh-115 In acetonitrile at 200 - 320℃; (g) phase;
GIPKh-115 In acetonitrile at 180 - 320℃; (g) phase. Object of study: effect of electronic factors;

: 4769-97-5
4-nitro-1H-indoIe

: 5192-23-4
4-amino-1H-indole

Conditions

Conditions	Yield
palladium In ethanol	100%
With sodium tetrahydroborate In water at 20℃; for 1h;	100%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 4h;	99%

: 4769-97-5
4-nitro-1H-indoIe

: 105-36-2
ethyl bromoacetate

: 594844-55-0
(4-nitro-indol-1-yl)-acetic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 36h;	100%

: 446-48-0
o-fluorobenzyl bromide

: 4769-97-5
4-nitro-1H-indoIe

: C15H11FN2O2

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 3.15h;	100%

: 4769-97-5
4-nitro-1H-indoIe

: 456-41-7
1-(Bromomethyl)-3-fluorobenzene

: C15H11FN2O2

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 3.15h;	100%

: 4769-97-5
4-nitro-1H-indoIe

: 459-46-1
4-Fluorobenzyl bromide

: C15H11FN2O2

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 3.15h;	100%

: 4769-97-5
4-nitro-1H-indoIe

: 89-92-9
2-methylbenzyl bromide

: C16H14N2O2

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 3.15h;	100%

: 4769-97-5
4-nitro-1H-indoIe

: 620-13-3
1-bromomethyl-3-methyl-benzene

: C16H14N2O2

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 3.15h;	100%

: 4769-97-5
4-nitro-1H-indoIe

: 104-81-4
4-Methylbenzyl bromide

: C16H14N2O2

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 3.15h;	100%

: 4769-97-5
4-nitro-1H-indoIe

: 93321-44-9
1,3-diphenylprop-2-yn-1-yl acetate

: 3-(1,3-diphenylprop-2-ynyl)-4-nitro-1H-indole

Conditions

Conditions	Yield
With indium(III) chloride In acetonitrile at 20℃; for 3h;	99%
With iodine In dichloromethane at 20℃; for 24h;	79%

: 4769-97-5
4-nitro-1H-indoIe

: 74-88-4
methyl iodide

: 91482-63-2
1-methyl-4-nitro-1H-indole

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 2h; cooling;	98%
Stage #1: 4-nitro-1H-indoIe With sodium hydride In N,N-dimethyl-formamide Cooling with ice; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 4h;	95%
Stage #1: 4-nitro-1H-indoIe With potassium hydroxide In acetone at 0℃; Stage #2: methyl iodide In acetone at 20℃; for 2h;	85.14%

: 4769-97-5
4-nitro-1H-indoIe

: 431-47-0
trifluoroacetic acid-methyl ester

: 91482-63-2
1-methyl-4-nitro-1H-indole

Conditions

Conditions	Yield
Stage #1: 4-nitro-1H-indoIe With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.0833333h; Stage #2: trifluoroacetic acid-methyl ester In N,N-dimethyl-formamide; mineral oil for 4h;	98%

: 4769-97-5
4-nitro-1H-indoIe

: 41600-21-9
methyl 2-oxo-2-(pyrrolidin-1-yl)acetate

: 115118-95-1
methyl (4-nitroindol-3-yl)-2-oxoacetate

Conditions

Conditions	Yield
With pyrophosphoryl chloride at 0 - 20℃; Vilsmeier glyoxylation;	97%
With pyrophosphoryl chloride at 20℃; for 3h;	63%
Stage #1: 4-nitro-1H-indoIe; methyl 2-oxo-2-(pyrrolidin-1-yl)acetate With pyrophosphoryl chloride at 20℃; Cooling with ice; Stage #2: With methanol; sodium hydrogencarbonate In water at 0℃;	15%

: 4769-97-5
4-nitro-1H-indoIe

: 75-36-5
acetyl chloride

: 4769-95-3
1-(4-nitro-1H-indol-3-yl)ethan-1-one

Conditions

Conditions	Yield
With aluminum (III) chloride; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride	97%
With aluminium trichloride; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 20℃; Friedel-Crafts acylation;	87%

: 4769-97-5
4-nitro-1H-indoIe

: 98-09-9
benzenesulfonyl chloride

: 850655-62-8
4-nitro-1-(phenylsulfonyl)-1H-indole

Conditions

Conditions	Yield
Stage #1: 4-nitro-1H-indoIe With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: benzenesulfonyl chloride In N,N-dimethyl-formamide at 0 - 20℃; Stage #3: With water; ammonium chloride In N,N-dimethyl-formamide	97%
Stage #1: 4-nitro-1H-indoIe With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.333333h; Inert atmosphere; Stage #2: benzenesulfonyl chloride In tetrahydrofuran for 1h; Inert atmosphere;	95%
Stage #1: 4-nitro-1H-indoIe With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil for 1h; Inert atmosphere;	95%

: 4769-97-5
4-nitro-1H-indoIe

: 87751-69-7
rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene

: 1304665-66-4
C23H18N2O2

Conditions

Conditions	Yield
With amberlyst-15 In acetonitrile at 20℃; for 8h;	97%

: 4769-97-5
4-nitro-1H-indoIe

: 100-39-0
benzyl bromide

: 81038-29-1
1-benzyl-4-nitro-1H-indole

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; benzene for 17h;	96.8%
Stage #1: 4-nitro-1H-indoIe With sodium hydride In N,N-dimethyl-formamide Cooling with ice; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 4h;	93%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; Schlenk technique;	62%

: 4769-97-5
4-nitro-1H-indoIe

: 349-88-2
4-Fluorobenzenesulfonyl chloride

: 1131453-08-1
1-(4'-fluorobenzenesulfonyl)-4-nitro-1H-indole

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran at 25 - 30℃;	96.44%

: 4769-97-5
4-nitro-1H-indoIe

: 30438-74-5
N-(chloromethyl)dimethylamine

: 7150-46-1
4-nitrogramine

Conditions

Conditions	Yield
In acetic acid	96%

: 4769-97-5
4-nitro-1H-indoIe

: 91482-63-2
1-methyl-4-nitro-1H-indole

Conditions

Conditions	Yield
	96%

: 4769-97-5
4-nitro-1H-indoIe

: 616-38-6
carbonic acid dimethyl ester

: 91482-63-2
1-methyl-4-nitro-1H-indole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 2h; Green chemistry;	96%

: 4769-97-5
4-nitro-1H-indoIe

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

: 913836-24-5
tert-butyl 4-nitro-1H-indole-1-carboxylate

Conditions

Conditions	Yield
dmap In dichloromethane at 0 - 20℃;	95%
dmap In toluene at 20℃; for 1.75h; Product distribution / selectivity;	95.8%
With triethylamine In dichloromethane at 0℃; for 2h;	71%

: 4769-97-5
4-nitro-1H-indoIe

: 79-22-1
methyl chloroformate

: 81038-41-7
1-methoxycarbonyl-4-nitroindole

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 4h;	95.1%
With sodium hydride	93%

: 4769-97-5
4-nitro-1H-indoIe

: 7051-34-5
cyclopropylcarbinyl bromide

: 1262797-29-4
1-cyclopropylmethyl-4-nitro-1H-indole

Conditions

Conditions	Yield
Stage #1: 4-nitro-1H-indoIe With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Stage #2: cyclopropylcarbinyl bromide In N,N-dimethyl-formamide; mineral oil	95%

: 4769-97-5
4-nitro-1H-indoIe

: 56-45-1
L-serin

: 4-nitro-1-tryptophan

Conditions

Conditions	Yield
With Pf2A6 enzyme In aq. phosphate buffer; water; dimethyl sulfoxide at 75℃; for 12h; pH=8; Reagent/catalyst; Enzymatic reaction;	95%
With tryptophan synthase from Salmonella typhimurium cell lysate In aq. phosphate buffer at 37℃; for 72h; pH=7.4; Enzymatic reaction;

: 4769-97-5
4-nitro-1H-indoIe

: 5394-18-3
2-(4-bromobutyl)isoindoline-1,3-dione

: 882032-51-1
2-(4-(4-nitro-1H-indol-1-yl)butyl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 86℃; for 23h;	94.5%

: 4769-97-5
4-nitro-1H-indoIe

: 95-92-1
oxalic acid diethyl ester

: 91482-64-3
1-ethyl-4-nitro-1H-indole

Conditions

Conditions	Yield
With potassium ethoxide In N,N-dimethyl-formamide Heating;	94%

4-Nitroindole Specification

The 4-Nitroindole, with the CAS registry number 4769-97-5, has the IUPAC name of 4-nitro-1H-indole. For being a kind of yellow crystalline solid, it is usually applied as the organic synthesis reagent and its product categories are including blocks; IndolesOxindoles; NitroCompounds; Indoles and derivatives; Indole; Indole Derivatives; Indoles; Simple Indoles; Building Blocks; Heterocyclic Building Blocks; Heterocyclic Building Blocks.

The characteristics of this chemical are as follows: (1)#H bond acceptors: 4; (2)#H bond donors: 1; (3)#Freely Rotating Bonds: 1; (4)Polar Surface Area: 50.75; (5)Index of Refraction: 1.723; (6)Molar Refractivity: 45.07 cm³; (7)Molar Volume: 113.7 cm³; (8)Polarizability: 17.86 ×10^-24 cm³; (9)Surface Tension: 67.7 dyne/cm; (10)Density: 1.425 g/cm³; (11)Flash Point: 173.1 °C; (12)Enthalpy of Vaporization: 58.46 kJ/mol; (13)Boiling Point: 362.6 °C at 760 mmHg; (14)Vapour Pressure: 3.98E-05 mmHg at 25°C; (15)Exact Mass: 162.042927; (16)MonoIsotopic Mass: 162.042927; (17)Topological Polar Surface Area: 61.6; (18)Heavy Atom Count: 12; (19)Complexity: 190.

When you are dealing with this chemical, you should be very careful. For one thing, it is irritant which may cause inflammation to the skin or other mucous membranes. For another thing, it is harmful which may cause damage to health, and it will have possible risk of irreversible effects. Therefore, you should take the following instructions. Wear suitable protective clothing and gloves, and if in case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).

Additionally, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1=CC2=C(C=CN2)C(=C1)[N+](=O)[O-]
(2)InChI: InChI=1S/C8H6N2O2/c11-10(12)8-3-1-2-7-6(8)4-5-9-7/h1-5,9H
(3)InChIKey: LAVZKLJDKGRZJG-UHFFFAOYSA-N

Product Name

4-Nitroindole

Synthetic route

4-Nitroindole Specification

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