22190-33-6

Basic information

• Product Name: 5-BROMOINDOLINE
• Synonyms: 5-BROMOINDOLINE;AKOS BC-0891;5-BROMO-2,3-DIHYDRO-1H-INDOLE;5-Bromoindoline,98+%;5-Bromoindoline,97%;5-bromodihydroindole;1H-Indole, 5-broMo-2,3-dihydro-;5-BroMo-2,3-dihydroindole
• CAS NO: 22190-33-6
• Molecular Formula: C₈H₈BrN
• Molecular Weight: 198.06
• EINECS: -0
• Product Categories: Indoles and derivatives;Indoline & Oxindole;Halogenated Heterocycles;Heterocyclic Building Blocks;Indolines;IndolinesBuilding Blocks;Heterocycle-Indole series
• Mol File: 22190-33-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 36-40 °C(lit.)
• Boiling Point: 114-115°C 5mm
• Flash Point: >230 °F
• Appearance: White to brown low melting solid
• Density: 1.514 g/cm³
• Vapor Pressure: 0.00334mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: ?20°C
• Solubility: DMSO, Methanol
• PKA: 4.35±0.20(Predicted)
• BRN: 121590
• CAS DataBase Reference: 5-BROMOINDOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOINDOLINE(22190-33-6)
• EPA Substance Registry System: 5-BROMOINDOLINE(22190-33-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 22190-33-6(Hazardous Substances Data)

Usage

Uses

5-Bromoindoline is a brominated indoline derivative and a product of biocatalyzed halogenation of nucleobase analogs. 5-Bromoindoline is used in the synthetic preparation of biologically active compou nds such as selective human β3 adrenergic receptor agonists.

InChI:InChI=1/C8H8BrN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-2,5,10H,3-4H2

Upstream product

• 22190-38-1 5-bromo-N-acetylindoline 

Downstream Products

• 1027489-86-6 {(E)-(S)-4-(5-Bromo-2,3-dihydro-indol-1-yl)-4-oxo-1-[2-(trityl-carbamoyl)-ethyl]-but-2-enyl}-carbamic acid tert-butyl ester 
• 668261-20-9 methyl 3-bromo-5-[(5-bromo-2,3-dihydro-1H-indol-1-yl)sulfonyl]benzoate 
• 261732-38-1 tert-butyl 5-bromoindoline-1-carboxylate 
• 742698-83-5 5-bromo-1-cyclohexylindoline 
• 1194732-22-3 3-(5-bromo-2,3-dihydro-indol-1-yl)-azetidine-1-carboxylic acid tert-butyl ester 
• 1194731-94-6 4-benzyloxy-1-{1-[1-(2-fluoro-ethyl)-azetidin-3-yl]-2,3-dihydro-1H-indol-5-yl}-1H-pyridin-2-one 
• 1194731-78-6 4-(4-chloro-phenyl)-1-[1-(1-methyl-azetidin-3-yl)-2,3-dihydro-1H-indol-5-yl]-1H-pyridin-2-one 
• 1194731-76-4 4-(4-chloro-phenyl)-1-{1-[1-(2-fluoro-ethyl)-azetidin-3-yl]-2,3-dihydro-1H-indol-5-yl}-1H-pyridin-2- 
• 1194732-49-4 C₂₈H₃₁N₃O₄ 
• 1194732-27-8 3-{5-[4-(4-chloro-phenyl)-2-oxo-2H-pyridin-1-yl]-2,3-dihydro-indol-1-yl}-azetidine-1-carboxylic acid 
• 1194732-29-0 C₂₂H₂₀ClN₃O 
• 1194731-96-8 1-(1-azetidin-3-yl-2,3-dihydro-1H-indol-5-yl)-4-benzyloxy-1H-pyridin-2-one 
• 1194731-95-7 4-benzyloxy-1-[1-(1-methyl-azetidin-3-yl)-2,3-dihydro-1H-indol-5-yl]-1H-pyridin-2-one 
• 1442463-71-9 C₂₃H₁₉Br₂NO 

Relevant articles and documents

Efficient synthesis process of medical intermediate 5-bromoindole

The invention discloses an efficient synthesis process of a medical intermediate 5-bromoindole, comprising the following steps of: using an indole compound as a raw material, carrying out low-pressureliquid-phase hydrogenation to destroy five-membered ring conjugation of indole to obtain an indoline compound; enabling the indoline compound to react with an acylation reagent, and protecting nitrogen, so as to obtain an N-acyl indoline compound; carrying out bromination on the N-acyl indoline compound to obtain a 5-bromo-N-acyl indoline compound; carrying out deacylation protection on the 5-bromo-N-acyl indoline compound to obtain a 5-bromoindoline compound; and carrying out oxidative dehydrogenation on the 5-bromoindoline compound by using oxygen or air under the action of a cuprous catalyst and nitric oxide to obtain the target compound 5-bromoindole. The steps involved in the process are convenient to operate, the conditions are mild, and environmental pollution is reduced; finally,the prepared product is high in yield, high in purity and low in energy consumption.

Preparation method of drug intermediate 5-bromoindole

The invention relates to a preparation method of a drug intermediate 5-bromoindole. The preparation method uses an N-acyl indoline compound 3 as a raw material, a 5-bro-N-acyl indoline compound 4 is obtained through bromization, then a 5-bromoindole compound 5 is obtained through diacylation protection, and a target compound 6, namely 5-bromoindole, is obtained through oxidative dehydrogenation. The preparation method is suitable for large-scale production, the production cost is relatively lower, colors can be thoroughly removed through pure recrystallization, and the preparation method has the positive significance on application of the 5-bromoindole and quality control of relevant drugs.

Catalytic hydrogenation of functionalized amides under basic and neutral conditions

A new, base-free high turnover number (TON) catalyst for hydrogenation of simple and functionalized amides is prepared by reacting [Ru(η3-C3H5)(Ph2P(CH2)2NH2)2]BF4 and BH4- under hydrogen. The hydrogenation proceeds with C-N cleavage to form the corresponding amine and alcohol. The base-free and base-promoted hydrogenations tolerate alcohols, amines, aromatic bromides, chlorides and fluorides, ethers, certain olefins, and N-heterocyclic rings. The reaction was used to deprotect the amine groups in certain acetyl amides to form, for example, an N-heterocyclic amine containing an aryl bromide. The base-free system also selectively hydrogenates N-acyloxazolidinones without epimerization at the α-position, and reduced β-lactams to form the corresponding amino alcohols.