20200-86-6

Basic information

• Product Name: 1,3,3-Trimethyl-2,3-dihydro-1H-indole-2-one
• Synonyms: 1,3,3-Trimethyl-1H-indole-2(3H)-one;1,3,3-Trimethyl-2,3-dihydro-1H-indole-2-one;1,3,3-Trimethylindoline-2-one;1,3-Dihydro-1,3,3-trimethyl-2H-indol-2-one;2,3-Dihydro-1,3,3-trimethyl-1H-indole-2-one;1,3,3-Trimethyl-2,3-dihydro-1H-indol-2-one
• CAS NO: 20200-86-6
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.23
• Mol File: 20200-86-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: 50 °C
• Boiling Point: 333.3°C at 760 mmHg
• Flash Point: 156.8°C
• Appearance: /
• Density: 1.065g/cm³
• Vapor Pressure: 0.000138mmHg at 25°C
• Refractive Index: 1.539
• PKA: 0.49±0.40(Predicted)
• CAS DataBase Reference: 1,3,3-Trimethyl-2,3-dihydro-1H-indole-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,3-Trimethyl-2,3-dihydro-1H-indole-2-one(20200-86-6)
• EPA Substance Registry System: 1,3,3-Trimethyl-2,3-dihydro-1H-indole-2-one(20200-86-6)

Safety Data

• Hazardous Substances Data: 20200-86-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 797, 1956 DOI: 10.1021/ja01585a025

InChI:InChI=1/C11H13NO/c1-11(2)8-6-4-5-7-9(8)12(3)10(11)13/h4-7H,1-3H3

Upstream product

• 67-56-1 methanol 
• 1504-06-9 3-methylindolin-2-one 
• 124-41-4 sodium methylate 
• 74-88-4 methyl iodide 
• 108-24-7 acetic anhydride 
• 64473-30-9 1-Pyridin-4-yl-2-[1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidene]-ethanone 
• 105070-00-6 2,2'-bis-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-1,1'-p-phenylene-bis-ethanone 
• 1207280-38-3 methyl(2-(prop-1-en-2-yl)phenyl)carbamic chloride 
• 123-72-8 butyraldehyde 
• 5418-63-3 1,2,3,3-tetramethyl-3H-indolium iodide 
• 108-86-1 bromobenzene 
• 102804-50-2 N-(2-bromophenyl)-N-methylmethacrylamide 
• 154386-63-7 N-(2-iodophenyl)-N-methylmethacrylamide 
• 110992-55-7 IR-797 chloride 

Downstream Products

• 116916-57-5 3-Mercapto-2-[1-methyl-3,3-diphenyl-1,3-dihydro-indol-(2E)-ylidene]-propionitrile 
• 66113-37-9 5-chloro-1,3,3-trimethylindoline 
• 4676-98-6 5-benzyloxy-1,3,3-trimethylindoline 
• 953048-71-0 5-amino-1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one 
• 19155-24-9 3,3-dimethyloxindole 

Relevant articles and documents

A Platinum(II) Complex of Heptamethine Cyanine for Photoenhanced Cytotoxicity and Cellular Imaging in Near-IR Light

Controlled generation of cytotoxic agents with near-IR light is a current focus of photoactivated cancer therapy, including that involving cytotoxic platinum species. A heptamethine cyanine scaffolded PtII complex, IR797-Platin exhibits unprecedented Pt?O bond scission and enhancement in DNA platination in near-IR light. This complex also displayed significant singlet oxygen quantum yield thereby qualifying as a near-IR photodynamic therapeutic agent. The complex showed 30–60 fold enhancement of cytotoxicity in near-IR light in various cancer cell lines. The cellular imaging properties were also leveraged to observe its significant co-localization in cytoplasmic organelles. This is the first demonstration of a near-IR light-initiated therapy involving the cytotoxic effects of both active cisplatin and singlet oxygen.

Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes

An unprecedented asymmetric acyl-carbamoylation of pendant alkenes tethered on aryl carbamic chlorides with both aliphatic and aromatic aldehydes has been developed via the cooperative catalysis of a chiral nickel-PHOX complex and tetrabutylammonium decatungstate. This reaction represents the first example of merging hydrogen-atom-transfer photochemistry and asymmetric transition metal catalysis in difunctionalization of alkenes. Using this protocol, a variety of oxindoles bearing a challenging quaternary stereogenic center are furnished under mild conditions in highly enantioselective manner.

Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes by Domino Cyclization/Cross-Coupling

A Ni-catalyzed enantioselective reductive diarylation of activated alkenes by domino cyclizative/cross-coupling of two aryl bromides is developed. This reaction proceeds under very mild conditions and shows broad substrate scope, without requiring the use of preformed organometallic reagents. Moreover, this approach provides direct access to various bis-heterocycles bearing all-carbon quaternary centers in synthetically useful yields (up to 81%) with excellent enantioselectivity (>30 examples, 90-99% ee).