72561-51-4

Basic information

• Product Name: 3-AMINO-5-CHLOROINDOLE
• Synonyms: 3-AMINO-5-CHLOROINDOLE;5-CHLORO-1H-INDOL-3-AMINE;5-Chloro-1H-indol-3-ylaMine
• CAS NO: 72561-51-4
• Molecular Formula: C₈H₇ClN₂
• Molecular Weight: 166.61
• Mol File: 72561-51-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 387.5 °C at 760 mmHg
• Flash Point: 188.2 °C
• Appearance: /
• Density: 1.435 g/cm³
• Vapor Pressure: 3.27E-06mmHg at 25°C
• Refractive Index: 1.757
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 3-AMINO-5-CHLOROINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-5-CHLOROINDOLE(72561-51-4)
• EPA Substance Registry System: 3-AMINO-5-CHLOROINDOLE(72561-51-4)

Safety Data

• Hazardous Substances Data: 72561-51-4(Hazardous Substances Data)

Usage

General Description

3-Amino-5-chloroindole is a chemical compound with the molecular formula C8H7ClN2. As an indole derivative, it forms part of a wide variety of bioactive compounds, and it has potential applications in the synthesis of pharmaceuticals and other complex organic molecules. The presence of the amino and chloro groups can make it a versatile intermediate in chemical reactions. Its physical and safety properties, as well as its specificity in reactions, can vary and should be handled by trained professionals under controlled environments. As of now, there is limited information about this compound in the public domain, suggesting it may be a subject of ongoing research and development.

InChI:InChI=1/C8H7ClN2/c9-5-1-2-8-6(3-5)7(10)4-11-8/h1-4,11H,10H2

Upstream product

• 76983-62-5 5-Chloro-3-nitroso-1H-indole 
• 213542-01-9 5-chloro-3-nitro-1H-indole 
• 17422-32-1 5-chloro-1H-indole 

Downstream Products

• 76983-72-7 2-[(5-Chloro-1H-indol-3-yl)-hydrazono]-propionic acid ethyl ester 
• 93704-54-2 N-(5-Chloro-1H-indol-3-yl)-benzene-1,2-diamine 
• 936243-91-3 N,N'-bis-Boc-N''-(5-chloro-1H-indol-3-yl)guanidine 
• 93704-63-3 2-Chloro-6-methyl-5,12-dihydro-benzo[2,3][1,4]diazepino[6,5-b]indole 
• 93704-58-6 N-[2-(5-Chloro-1H-indol-3-ylamino)-phenyl]-acetamide 

Relevant articles and documents

Design, synthesis, and biological evaluation of substituted-N-(thieno[2,3-b]pyridin-3-yl)-guanidines, N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidines, and N-(1H-indol-3-yl)-guanidines

Sulfonylureas stimulate insulin secretion independent of the blood glucose concentration and therefore cause hypoglycemia in type 2 diabetic patients. Over the last years, a number of aryl-imidazoline derivatives have been identified that stimulate insulin secretion in a glucose-dependent manner. In the present study, we have developed three series of substituted N-(thieno[2,3-b]pyridin-3-yl)-guanidine (2a-l), N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidine (3a-l), and N-(1H-indol-3-yl)-guanidine (4a-l) as new class of antidiabetic agents. In vitro glucose-dependent insulinotropic activity of test compounds 2a-l, 3a-l, and 4a-l was evaluated using RIN5F (Rat Insulinoma cell) based assay. All the test compounds showed concentration-dependent insulin secretion, only in presence of glucose load (16.7 mmol). Some of the test compounds (2c, 3c, and 4c) from each series were found to be equipotent to BL 11282 (standard aryl-imidazoline), which indicated that the guanidine group acts as a bioisostere of imidazoline ring system.

Synthesis of 3-Aminoindoles & Ethyl Pyrroloindole-2-carboxylates

Various indoles (1a-g) on nitrosation with sodium nitrite and acetic acid yield the corresponding 3-nitrosoindoles (2a-g).These on reduction with sodium dithionate, in the presence of 2 N NaOH, afford 3-aminoindoles (3a-g) in good yields.Coupling of a diazotised solution of 3a-g with ethyl α-methylacetoacetate (5) yields the respective ethyl indol-3-ylpyruvate hydrazones (6a-g) which on Fischer indolization with alcoholic H2SO4 give various ethyl pyrroloindole-2-carboxylates (7a-g).