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53924-05-3

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53924-05-3 Usage

Chemical Properties

Beige-yellowish powder

Uses

7-Chloroindole may be used in the preparation of 1-methyl-7-chloroindole and glycosylated 7-chloroindole-3-acetamide.

General Description

7-Chloroindole is an indole derivative. It has been synthesized from 2,3-dihydroindole.

Check Digit Verification of cas no

The CAS Registry Mumber 53924-05-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,9,2 and 4 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 53924-05:
(7*5)+(6*3)+(5*9)+(4*2)+(3*4)+(2*0)+(1*5)=123
123 % 10 = 3
So 53924-05-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H6ClN/c9-7-3-1-2-6-4-5-10-8(6)7/h1-5,10H

53924-05-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (L17637)  7-Chloroindole, 98%   

  • 53924-05-3

  • 250mg

  • 368.0CNY

  • Detail
  • Alfa Aesar

  • (L17637)  7-Chloroindole, 98%   

  • 53924-05-3

  • 1g

  • 1242.0CNY

  • Detail
  • Aldrich

  • (473731)  7-Chloroindole  97%

  • 53924-05-3

  • 473731-1G

  • 1,027.26CNY

  • Detail

53924-05-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 7-Chloroindole

1.2 Other means of identification

Product number -
Other names 7-chloro-1H-indole

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:53924-05-3 SDS

53924-05-3Synthetic route

methyl 7-chloro-indole-1-carboxylate

methyl 7-chloro-indole-1-carboxylate

7-chloro-1H-indole
53924-05-3

7-chloro-1H-indole

Conditions
ConditionsYield
With potassium hydroxide In methanol for 1h; Reflux;98%
2,3-dihydro-7-chloro-1H-indole
114144-22-8

2,3-dihydro-7-chloro-1H-indole

7-chloro-1H-indole
53924-05-3

7-chloro-1H-indole

Conditions
ConditionsYield
With salcomine; oxygen In methanol at 20℃; for 24h;94%
With salcomine In methanol for 4h; Ambient temperature;70%
With palladium on activated charcoal In toluene at 135℃; for 15h;66%
With oxygen In methanol at 120℃; under 3800.26 Torr; for 12h;79 %Chromat.
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

(2-chlorophenyl)hydrazine
10449-07-7

(2-chlorophenyl)hydrazine

7-chloro-1H-indole
53924-05-3

7-chloro-1H-indole

Conditions
ConditionsYield
With phosphorus pentachloride; zinc(II) chloride for 0.0833333h; microwave irradiation;80%
7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole
642494-37-9

7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole

7-chloro-1H-indole
53924-05-3

7-chloro-1H-indole

Conditions
ConditionsYield
With copper dichloride In methanol; water at 80℃; for 4h;75%
With copper dichloride In methanol; water at 80℃; for 4.5h; Inert atmosphere; Schlenk technique;42%
7-chloroisatin
7477-63-6

7-chloroisatin

7-chloro-1H-indole
53924-05-3

7-chloro-1H-indole

Conditions
ConditionsYield
With potassium borohydride; boron trifluoride diethyl etherate In tetrahydrofuran at -10 - -5℃; Inert atmosphere;71%
3-chloro-2-nitrotoluene
5367-26-0

3-chloro-2-nitrotoluene

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

7-chloro-1H-indole
53924-05-3

7-chloro-1H-indole

Conditions
ConditionsYield
Stage #1: 3-chloro-2-nitrotoluene; N,N-dimethyl-formamide dimethyl acetal With pyrrolidine In 1,4-dioxane at 102℃; for 9h; Leimgruber-Batcho Indole Synthesis; Reflux; Inert atmosphere;
Stage #2: With hydrazine hydrate In 1,4-dioxane at 45℃; for 1h; Leimgruber-Batcho Indole Synthesis;
70%
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

A

2-oxoindole
59-48-3

2-oxoindole

B

7-chloro-1H-indole
53924-05-3

7-chloro-1H-indole

Conditions
ConditionsYield
In tetrahydrofuran at -40℃;A 33%
B 63%
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

7-chloro-1H-indole
53924-05-3

7-chloro-1H-indole

Conditions
ConditionsYield
Stage #1: vinyl magnesium bromide; 2-Chloronitrobenzene In tetrahydrofuran at -40 - 0℃; for 2.5h; Bartoli Indole Synthesis;
Stage #2: With ammonium chloride In tetrahydrofuran at 0℃; for 0.5h; Bartoli Indole Synthesis;
60%
In tetrahydrofuran at -40℃; for 1h;56%
vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

A

7-chloro-1H-indole
53924-05-3

7-chloro-1H-indole

B

3,3’-ethane-1,1-diylbis(7-chloro-1H-indole)
1445721-16-3

3,3’-ethane-1,1-diylbis(7-chloro-1H-indole)

Conditions
ConditionsYield
Stage #1: vinyl magnesium bromide; 2-Chloronitrobenzene In tetrahydrofuran at -40 - 0℃; for 2.5h;
Stage #2: With potassium hydrogensulfate In tetrahydrofuran; water at 0℃; for 0.5h; Reagent/catalyst;
A 8%
B 34%

53924-05-3Relevant articles and documents

Reversible aerobic oxidative dehydrogenation/hydrogenation of N-heterocycles over AlN supported redox cobalt catalysts

He, Zhen-Hong,Sun, Yong-Chang,Wang, Kuan,Wang, Zhong-Yu,Guo, Pan-Pan,Jiang, Chong-Shan,Yao, Man-Qing,Li, Zhu-Hui,Liu, Zhao-Tie

, (2020/09/16)

N-heterocycles with quinoline and tetrahydroquinoline structures are highly important in pharmaceutical and chemical industries, and their highly efficient mutual transformations are vital but still challenging. In the present work, AlN supported redox cobalt catalysts (Co3O4/AlN and Co/AlN) were prepared, which could achieve the reversible aerobic oxidative dehydrogenation/hydrogenation of N-heterocycles with good performances. The catalytic performances were stem from the strong interaction between Co species with AlN support, which were confirmed by the characterizations of Raman, XPS, UV–vis DRS, and H2-TPR etc. Both of the catalysts showed good stabilities and reusabilities for the titled reactions. Besides, the gram-scale experiments achieved with good yields to corresponding products, revealing the present protocol possesses great potential applications in industry. The strategy of using redox Co-based catalyst not only provides a potential catalyst for the reversible hydrogenation/oxidative dehydrogenation reactions but also replenishes methods for constructing of other redox catalyst, especially with AlN as a carrier.

Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis

Ning, Xiao-Shan,Liang, Xin,Hu, Kang-Fei,Yao, Chuan-Zhi,Qu, Jian-Ping,Kang, Yan-Biao

supporting information, p. 1590 - 1594 (2018/04/30)

A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).

Synthesis of 7-halo indoles (by machine translation)

-

, (2017/01/12)

The present invention relates to synthesis of 7? Halo indole method, comprising the steps of:O-halogenated aniline, chloral hydrate and hydroxylamine hydrochloride by the Sandmeyer reaction to synthesize 7? halogenating isatin ; 7? halogenating isatin dissolved with an organic solvent, in the reducing agent by reduction reaction under the conditions of 7? Halo indole, the reducing agent is an alkali metal borohydride system, four system adopts, lithium hydride system or triethyl silane system. The beneficial effect of the invention is:in order to O-halogenated aniline and the chloral hydrate is, hydroxylamine hydrochloride as raw materials, by the Sandmeyer shall synthesis method for preparing compositions b isonitroso 7? halogenating isatin, and then by further reduction and system reduction to prepare 7? Halo indole; by the 7? Preparation halogenating isatin 7? Halo indole method, the raw material is easy to obtain, low price, higher process yield, the product purity is good, simple operation, and the like, is suitable for batch preparation 7? Halo indole. (by machine translation)

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