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68742-28-9 Usage

General Description

5-Ethylindole is an organic compound with the formula C11H11N. It is a derivative of indole, with an ethyl group attached to the five position of the indole ring. It is a pale yellow liquid at room temperature and is insoluble in water. 5-Ethylindole is commonly used as an intermediate in the synthesis of pharmaceuticals, pesticides, and other organic compounds. It is also used as a precursor in the production of dyes and pigments. It has been identified as a potential mutagen in bacterial and mammalian cells, and caution should be exercised in handling and disposing of this chemical.

Check Digit Verification of cas no

The CAS Registry Mumber 68742-28-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,8,7,4 and 2 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 68742-28:
(7*6)+(6*8)+(5*7)+(4*4)+(3*2)+(2*2)+(1*8)=159
159 % 10 = 9
So 68742-28-9 is a valid CAS Registry Number.

68742-28-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-ethyl-1H-indole

1.2 Other means of identification

Product number -
Other names 1H-Indole,5-ethyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:68742-28-9 SDS

68742-28-9Synthetic route

5-(2-(phenylsulfonyl)ethyl)-1H-indole
1225327-16-1

5-(2-(phenylsulfonyl)ethyl)-1H-indole

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
With magnesium In methanol at 60 - 64℃; Inert atmosphere;98.5%
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

triethyl borane
97-94-9

triethyl borane

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;85%
5-ethynyl-1H-indole
889108-48-9

5-ethynyl-1H-indole

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol under 750.06 Torr; for 2h;82%
5-ethylindole-2-carboxylic acid
140397-32-6

5-ethylindole-2-carboxylic acid

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
With quinoline; copper chromite at 240℃; for 3h;67.8%
5-ethyl-1H-indole-2-carboxylic acid
37033-93-5

5-ethyl-1H-indole-2-carboxylic acid

A

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

B

5-ethenyl-1H-indole
77132-99-1

5-ethenyl-1H-indole

Conditions
ConditionsYield
K-16 In benzene at 550℃;A 14%
B 26%
K-16 In benzene at 500℃; Product distribution; also with ethyl 5-ethylindole-2-carboxylate, other conditions;
Acetaldehyde p-ethylphenylhydrazone
77691-75-9

Acetaldehyde p-ethylphenylhydrazone

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
aluminum oxide In benzene at 300℃; for 0.333333h;25%
aluminum oxide In benzene at 300℃; for 0.333333h; Product distribution; Different temperatures and amount of catalyst;25%
ethyl 5-ethylindole-2-carboxylate
37033-94-6

ethyl 5-ethylindole-2-carboxylate

A

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

B

5-ethenyl-1H-indole
77132-99-1

5-ethenyl-1H-indole

Conditions
ConditionsYield
K-16 In benzene at 550℃;A n/a
B 21%
K-16 In benzene at 400℃;
ammonium salt of/the/ 5-ethyl-indole-2-carboxylic acid

ammonium salt of/the/ 5-ethyl-indole-2-carboxylic acid

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
With glass powder at 220℃;
ethylene glycol
107-21-1

ethylene glycol

4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
With silica gel; zirconium(IV) oxide at 309.85℃;42.6 % Chromat.
5-((trifluoromethyl)ethynyl)-1H-indole
884010-34-8

5-((trifluoromethyl)ethynyl)-1H-indole

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 101 mg / NaOH / methanol / 2 h / 20 °C
2: 82 percent / H2 / Pd/C / methanol / 2 h / 750.06 Torr
View Scheme
5-iodo-1H-indole
16066-91-4

5-iodo-1H-indole

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CuI; Et3N / Pd(PPh3)4 / acetonitrile / 4 h / Heating
2: 101 mg / NaOH / methanol / 2 h / 20 °C
3: 82 percent / H2 / Pd/C / methanol / 2 h / 750.06 Torr
View Scheme
5-Ethyl-1H-indole-3-carboxylic acid ethyl ester

5-Ethyl-1H-indole-3-carboxylic acid ethyl ester

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / aq. KOH / aq. ethanol / 1 h / Heating
2: 67.8 percent / quinoline, copper chromite / 3 h / 240 °C
View Scheme
4-aminoethylbenzene
589-16-2

4-aminoethylbenzene

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) NaNO2, aq. HCl, 2.) 50percent aq. KOH
2: 98 percent / aq. KOH / aq. ethanol / 1 h / Heating
3: 67.8 percent / quinoline, copper chromite / 3 h / 240 °C
View Scheme
5-ethyl-1-triisopropylsilanyl-1H-indole
835614-51-2

5-ethyl-1-triisopropylsilanyl-1H-indole

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
With ammonium fluoride In tetrahydrofuran; methanol at 20℃; for 72h;
1H-indole-5-carboxaldehyde
1196-69-6

1H-indole-5-carboxaldehyde

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / -10 °C
1.2: -78 - 20 °C
2.1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 20 °C / 760 Torr
View Scheme
5-ethenyl-1H-indole
77132-99-1

5-ethenyl-1H-indole

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760 Torr; for 12h;242 mg
5-bromo-1H-indole
10075-50-0

5-bromo-1H-indole

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / N,N-dimethyl-formamide / 4 h / 100 - 115 °C
2: hydrogen / methanol / 7 h / 20 °C / 3620.13 - 3878.71 Torr
3: magnesium / methanol / 60 - 64 °C / Inert atmosphere
View Scheme
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

N,N-dimethylamine hydro chloride

N,N-dimethylamine hydro chloride

(5-ethyl-1H-indol-3-ylmethyl)-dimethyl-amine
74367-51-4

(5-ethyl-1H-indol-3-ylmethyl)-dimethyl-amine

Conditions
ConditionsYield
With formaldehyd In ethyl acetate97%
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

formaldehyd
50-00-0

formaldehyd

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

(5-ethyl-1H-indol-3-ylmethyl)-dimethyl-amine
74367-51-4

(5-ethyl-1H-indol-3-ylmethyl)-dimethyl-amine

Conditions
ConditionsYield
Stage #1: 5-ethyl-1H-indole; formaldehyd; N,N-dimethylammonium chloride In water; isopropyl alcohol for 2h; Heating / reflux;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
97%
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

acetone
67-64-1

acetone

C23H26N2

C23H26N2

Conditions
ConditionsYield
With Langlois reagent In acetonitrile at 25℃; for 24h; UV-irradiation;80%
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

methyl iodide
74-88-4

methyl iodide

1-methyl-5-ethylindole
85654-47-3

1-methyl-5-ethylindole

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 65℃; for 6h;76%
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

2,6-di-tert-butyl-4-(2-(phenylethynyl)benzylidene)cyclohexa-2,5-dienone

2,6-di-tert-butyl-4-(2-(phenylethynyl)benzylidene)cyclohexa-2,5-dienone

2,6-di-tert-butyl-4-(2-ethyl-6-phenyl-5,12-dihydrobenzo[4,5]cyclohepta[1,2-b]indol-12-yl)phenol

2,6-di-tert-butyl-4-(2-ethyl-6-phenyl-5,12-dihydrobenzo[4,5]cyclohepta[1,2-b]indol-12-yl)phenol

Conditions
ConditionsYield
With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 2.5h; Inert atmosphere;76%
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

O-ethylhydroxylamine hydrochloride
3332-29-4

O-ethylhydroxylamine hydrochloride

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

N-ethoxy-5-ethyl-1H-indole-1-carboxamide

N-ethoxy-5-ethyl-1H-indole-1-carboxamide

Conditions
ConditionsYield
Stage #1: O-ethylhydroxylamine hydrochloride With sodium hydroxide In tetrahydrofuran at 20℃; for 3h;
Stage #2: 5-ethyl-1H-indole; 1,1'-carbonyldiimidazole With dmap In tetrahydrofuran; acetonitrile at 85℃; for 10h; Inert atmosphere;
Stage #3: O-ethylhydroxylamine hydrochloride In tetrahydrofuran at 80℃; for 6h; Inert atmosphere;
75%
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

5,5'-diethylindigo
79097-83-9

5,5'-diethylindigo

Conditions
ConditionsYield
With Cumene hydroperoxide; acetic acid; molybdenum hexacarbonyl In tert-butyl alcohol for 0.5h; Reflux;48%
maleiimide
541-59-3

maleiimide

5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

A

3-(2,5-dioxopyrrolidin-3-yl)-5-ethyl-1H-indole

3-(2,5-dioxopyrrolidin-3-yl)-5-ethyl-1H-indole

B

8-ethyl-11H-2,5,11-triaza-benzo[a]trindene-1,3,4,6-tetraone

8-ethyl-11H-2,5,11-triaza-benzo[a]trindene-1,3,4,6-tetraone

C

2,10-diethyl-6,8-dihydro-5H,7H,13H-indolo[3,2-a]pyrrolo[3,4-c]carbazole-6,8-dione

2,10-diethyl-6,8-dihydro-5H,7H,13H-indolo[3,2-a]pyrrolo[3,4-c]carbazole-6,8-dione

Conditions
ConditionsYield
With acetic acid for 15h; Michael addition; Heating;A 30%
B 6%
C 2%
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

5-ethyl-octahydro-indole

5-ethyl-octahydro-indole

Conditions
ConditionsYield
With acetic acid; platinum Hydrogenation;
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

A

indole
120-72-9

indole

B

5-methyl-1H-indole
614-96-0

5-methyl-1H-indole

C

5-ethenyl-1H-indole
77132-99-1

5-ethenyl-1H-indole

Conditions
ConditionsYield
K-16 In benzene at 550℃; under 735.5 Torr; for 6h; Product distribution; Various temperatures and concentrations of catalyst and 5-ethylindole;A 2.3 % Chromat.
B 3.3 % Chromat.
C 58.3 % Chromat.
K-16 In benzene at 550℃; under 735.5 Torr; for 6h;A 2.3 % Chromat.
B 3.3 % Chromat.
C 58.3 % Chromat.
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

5-ethenyl-1H-indole
77132-99-1

5-ethenyl-1H-indole

Conditions
ConditionsYield
K-16 In benzene at 502.9℃; Kinetics; Rate constant; Thermodynamic data; vapour phase; other temperature;
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

Sodium; 5-ethyl-1H-indole-3-thiolate

Sodium; 5-ethyl-1H-indole-3-thiolate

Conditions
ConditionsYield
With sodium hydroxide; iodine; thiourea; potassium iodide 1.) MeOH, RT, 2 h, 2.) MeOH, 90 deg C, 30 min; Multistep reaction;
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

oxalyl dichloride
79-37-8

oxalyl dichloride

2-(5-Ethyl-1H-indol-3-yl)-2-oxo-acetamide
159730-27-5

2-(5-Ethyl-1H-indol-3-yl)-2-oxo-acetamide

Conditions
ConditionsYield
With ammonium hydroxide 1.) Et2O, RT, 1 h, 2.) Et2O, RT, 4 h; Yield given. Multistep reaction;
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

oxalyl dichloride
79-37-8

oxalyl dichloride

dimethyl amine
124-40-3

dimethyl amine

2-(5-Ethyl-1H-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide

2-(5-Ethyl-1H-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide

Conditions
ConditionsYield
1.) Et2O, RT, 1 h, 2.) Et2O, H2O, RT, overnight; Yield given. Multistep reaction;
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

oxalyl dichloride
79-37-8

oxalyl dichloride

(5-ethyl-1H-indol-3-yl)-oxo-acetyl chloride
172896-14-9

(5-ethyl-1H-indol-3-yl)-oxo-acetyl chloride

Conditions
ConditionsYield
In diethyl ether Acylation; Heating;
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

N-benzyloxycarbonyl-D-proline acid chloride
61350-62-7

N-benzyloxycarbonyl-D-proline acid chloride

2-(5-ethyl-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester

2-(5-ethyl-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester

Conditions
ConditionsYield
Stage #1: 5-ethyl-1H-indole With ethylmagnesium bromide In tetrahydrofuran at 0℃; for 0.5h; Metallation;
Stage #2: N-benzyloxycarbonyl-D-proline acid chloride In tetrahydrofuran at 0℃; for 1.5h; Acylation;
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

2-(5-Ethyl-1H-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide

2-(5-Ethyl-1H-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether / Heating
2: Et3N / tetrahydrofuran / 2 h / 20 °C
View Scheme
5-ethyl-1H-indole
68742-28-9

5-ethyl-1H-indole

[2-(5-Ethyl-1H-indol-3-yl)-ethyl]-dimethyl-amine

[2-(5-Ethyl-1H-indol-3-yl)-ethyl]-dimethyl-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diethyl ether / Heating
2: Et3N / tetrahydrofuran / 2 h / 20 °C
3: LAH / tetrahydrofuran / 4 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 1.) Et2O, RT, 1 h, 2.) Et2O, H2O, RT, overnight
2: LiAlH4 / tetrahydrofuran / 72 h / Heating
View Scheme

68742-28-9Relevant articles and documents

SYNTHESIS OF 5-VINYLINDOLE BY SIMULTANEOUS DEHYDROGENATION AND DECARBOXYLATION OF 5-ETHYL-INDOLE-2-CARBOXYLIC ACID AND ITS ETHYL ESTER

Starostenko, N. E.,Dat, Fung Tien,Serova, I. A.,Kamenetskii, A. V.,Suvorov, N. N.

, p. 508 - 511 (1991)

A new method is proposed for the synthesis of 5-vinylindole by simultaneous catalytic dehydrogenation and decarboxylation of 5-ethylindole-2-carboxylic acid and its ethyl ester, making it possible to more than double the yield of the previously described method.

5,5′-alkylsubsituted indigo for solution-processed optoelectronic devices

Watanabe, Motonori,Uemura, Naoki,Ida, Shintaro,Hagiwara, Hidehisa,Goto, Kenta,Ishihara, Tatsumi

, p. 4280 - 4287 (2016/07/06)

A series of alkylated indigos were synthesized. Alkylated indigos were characterized by NMR, mass spectrometry, absorption spectra, cyclic voltammetry, and density functional theory (DFT) calculations. Propyl and butyl group substituted indigo was most soluble in chloroform and 1,2-dicrolobenzene, and these solubility were 65–89 times increased as compared to the parent indigo. DFT calculations suggested that the presence of the alkyl chains at the 5.5′-position increases the energy of the highest occupied molecular orbital, while reducing the energy of the lowest unoccupied molecular orbital. This theoretical finding was in good agreement with the experimental results. Crystal structures obtained by X-ray diffraction showed one-dimensional pi–pi stacking. Alkylated molecules were converted to leuco structure, and these structures were then converted to the corresponding indigos in the film state. After deposition of the films on TiO2/FTO substrate, oxidative photocurrents were observed.

Synthesis and biological evaluation of new dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones, substituted with various saturated and unsaturated side chains via palladium catalyzed cross-coupling reactions

Henon, Helene,Anizon, Fabrice,Golsteyn, Roy M.,Leonce, Stephane,Hofmann, Robert,Pfeiffer, Bruno,Prudhomme, Michelle

, p. 3825 - 3834 (2007/10/03)

The syntheses of a series of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones, substituted in 10-position with saturated and unsaturated side chains, via palladium catalyzed cross-coupling reactions, are described. These compounds can be considered as granulatimide bis-imide analogues. Their inhibitory activity toward Chk1 kinase and their antiproliferative activities in vitro in four tumor cell lines are reported.

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