33632-27-8

Basic information

• Product Name: 1-ACETYL-5-NITROINDOLINE
• Synonyms: 1-Acetyl-5-nitroindoline ,97%;1-(5-Nitro-indoline-1-yl)ethanone;1-Acetyl-2,3-dihydro-5-nitro-1H-indole;1-Acetyl-5-nitroindoline,98%;1-(5-Nitro-2,3-dihydro-1H-indol-1-yl)ethanone;1-(5-Nitro-2,3-dihydro-1H-indol-1-yl)ethan-1-one, TECH;1-Acetoxy-5-Nitroindoline;1-(5-nitro-1-indolinyl)ethanone
• CAS NO: 33632-27-8
• Molecular Formula: C₁₀H₁₀N₂O₃
• Molecular Weight: 206.2
• EINECS: 251-609-5
• Product Categories: Building Blocks;C10;Chemical Synthesis;Heterocyclic Building Blocks;Indoles
• Mol File: 33632-27-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 175-176 °C(lit.)
• Boiling Point: 345.04°C (rough estimate)
• Flash Point: 235.9 °C
• Appearance: Yellow to beige crystalline powder
• Density: 1.2815 (rough estimate)
• Vapor Pressure: 7.1E-09mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: Refrigerator (+4°C)
• PKA: -3.28±0.20(Predicted)
• CAS DataBase Reference: 1-ACETYL-5-NITROINDOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETYL-5-NITROINDOLINE(33632-27-8)
• EPA Substance Registry System: 1-ACETYL-5-NITROINDOLINE(33632-27-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: NM1892800
• TSCA: Yes
• Hazardous Substances Data: 33632-27-8(Hazardous Substances Data)

Usage

Chemical Properties

yellow to beige crystalline powder

InChI:InChI=1/C10H10N2O3/c1-7(13)11-5-4-8-6-9(12(14)15)2-3-10(8)11/h2-3,6H,4-5H2,1H3

Upstream product

• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 496-15-1 1-indoline 
• 108-24-7 acetic anhydride 
• 32692-19-6 5-nitro-2,3-dihydro-1H-indole 
• 75-36-5 acetyl chloride 
• 120-72-9 indole 

Downstream Products

• 32692-19-6 5-nitro-2,3-dihydro-1H-indole 
• 5192-03-0 5-amino-1H-indole 
• 15918-80-6 5-amino indoline 
• 114144-24-0 1-acetyl-2,3-dihydro-7-bromoindole 
• 87240-06-0 7-bromo-5-nitroindoline 
• 6019-39-2 N-(1H-indol-5-yl)benzamide 
• 220442-80-8 1-acetyl-7-bromo-5-nitro-indoline 
• 6146-52-7 5-nitroindole 
• 4993-96-8 1-(5-aminoindolin-1-yl)ethanone 
• 1612872-74-8 N-(1-acetyl-5-nitroindolin-7-yl)-4-methylbenzenesulfonamide 
• 4770-32-5 1-(5-hydroxy-2,3-dihydroindol-1-yl)ethanone 
• 1187212-51-6 N-((5-aminoindoline)sulfamoyl)benzamide 
• 1187212-54-9 N-((5-nitroindoline)sulfamoyl)benzamide 

Relevant articles and documents

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Improved preparation of some nitroindolines

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C5 nitration method of indoline compound

The invention discloses a C5 nitration method of an indoline compound. According to the method, cheap copper salt is used as a catalyst, organic small molecular tert-butyl nitrite (TBN) is used as a metal-free nitro source, and the air is used as an oxidizing agent. The above materials are subjected to C5 C-H functionalization in an organic solvent so as to realize C5 C-H nitration of the indolinecompound and obtain the C5 nitrated indoline compound. The method of the invention has advantages of simple reaction operation, low reaction cost, high yield, mild condition, no heavy metal pollution, etc.

Using weak interactions to control C-H mono-nitration of indolines

An unprecedented C-H mononitration of indolines either at the -C5 or -C7 positions under mild condition is reported here. The roles of multiple weak interactions and factors such as steric factors, electronic effects, cation-π interactions, and solvent polarity were established, and we achieved a 100% regioselective electrophilic aromatic (EArS) nitration using Cu(NO3)2 or AgNO3.