25981-82-2

Basic information

• Product Name: 2,3,3,5-Tetramethylindolenine
• Synonyms: 2,3,3,5-tetramethyl-3h-indol;2,3,3,5-TETRAMETHYL-3H-INDOLE;2,3,3,5-TETRAMETHYLINDOLENINE;AKOS BBS-00006369;2,3,3,5-TETRAMETHYL-3H-INDOLE: 98.5%;3H-Indole,2,3,3,5-tetraMethyl-;2,3,3,5-tetraMethyl-3H-indole, 2,3,3,5-triMethyl-3H-indole, 2,3,3,5-TetraMethylindole, 2,3,3,5-tetraMethyl-3H-indole, 2,3,3,5-TetraMethyl-3H-indol, 2,3,3,5-tetraMethylindolenyne
• CAS NO: 25981-82-2
• Molecular Formula: C₁₂H₁₅N
• Molecular Weight: 173.25
• EINECS: 1312995-182-4
• Product Categories: Indole;Heterocycle-Indole series;Benzopyrans ,Benzofurans
• Mol File: 25981-82-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 125°C/3mmHg(lit.)
• Flash Point: 96.3±28.2 °C
• Appearance: /
• Density: 1.0±0.1 g/cm³
• Vapor Pressure: 0.0361mmHg at 25°C
• Refractive Index: 1.5410 to 1.5450
• Storage Temp.: 2-8°C
• PKA: 6.55±0.40(Predicted)
• Water Solubility: Sparingly soluble in water.(0.26 g/L) (25°C),
• CAS DataBase Reference: 2,3,3,5-Tetramethylindolenine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,3,5-Tetramethylindolenine(25981-82-2)
• EPA Substance Registry System: 2,3,3,5-Tetramethylindolenine(25981-82-2)

Safety Data

• TSCA: Yes
• Hazardous Substances Data: 25981-82-2(Hazardous Substances Data)

Usage

Appearance

Light yellow to Brown clear liquid

Uses

2,3,3,5-Tetramethyl-3H-indole is used as a reactant in the preparation of cyanine borate salts.

InChI:InChI=1/C12H15N/c1-8-5-6-11-10(7-8)12(3,4)9(2)13-11/h5-7H,1-4H3

Upstream product

• 106-49-0 p-toluidine 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 119094-84-7 N-(1,2-dimethyl-propylidene)-N'-p-tolyl-hydrazine 
• 563-80-4 3-methyl-butan-2-one 
• 539-44-6 N-4-methylphenylhydrazine 

Downstream Products

• 93360-39-5 8,10,10-trimethyl-10a-(4-dimethylaminostyryl)-1,2,3,4,10,10a-hexahydropyrimido<1,2-a>indol-2-ones 
• 131527-04-3 2-methylene-3,3,5-trimethyl-1-(2-cyanobenzyl)-2,3-dihydro-1H-indole 
• 869559-29-5 1-benzyl-3,7,9,9,9a-pentamethyl-1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-one 
• 131527-02-1 2,3,3,5-tetramethyl-1-(2-cyanobenzyl)-3H-indolium bromide 

Relevant articles and documents

Oxidative electrochemical aryl C-C coupling of spiropyrans

The isolation and definitive assignment of the species formed upon electrochemical oxidation of nitro-spiropyran (SP) is reported. The oxidative aryl C-C coupling at the indoline moiety of the SP radical cation to form covalent dimers of the ring-closed SP form is demonstrated. The coupling is blocked with a methyl substituent para to the indoline nitrogen.

Iodine-Promoted Domino Oxidative Cyclization for the One-Pot Synthesis of Novel Fused Four-Ring Quinoxaline Fluorophores by sp3 C?H Functionalization

A method for the synthesis of novel fused four-ring quinoxaline skeleton has been described by an I2 promoted sp3 C?H functionalization between 1,2,3,3-tetramethyl-3H-indolium iodides and 1,2-diamines. This transformation proceeds smoothly under metal- and peroxide-free conditions through a sequential iodination, oxidation, annulation and rearrangement. Moreover, 8,9-dichloro-5,12,12-trimethyl-2-(trifluoromethyl)-5,12-dihydroquinolino[2,3-b]quinoxaline showed good photophysical properties and was used in live cell imaging, indicating the potential value of this skeleton as a fluorophore in probes.

Oxidative palladium(II)-catalyzed dehydrogenative C-H/C-H cross-coupling of 2,3-substituted indolines with arenes at the C7 position

Directed directing group: The C7 position of the indoline nucleus is difficult to address in C-H activation. An oxidative palladium(II) catalysis that allows for cross-dehydrogenative coupling in that position with activation of the C-H bond of the arene component is disclosed here. This C-H/C-H cross-coupling is applicable to various indolines acetylated at the nitrogen atom. Substitution at C2 is crucial for the C-H activation to occur at C7 (see scheme).