219605-52-4

Basic information

• Product Name: Benzenamine, 2-ethynyl-N,N-dimethyl-
• CAS NO: 219605-52-4
• Molecular Formula: C10H11N
• Molecular Weight: 145.204
• Mol File: 219605-52-4.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: Benzenamine, 2-ethynyl-N,N-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 2-ethynyl-N,N-dimethyl-(219605-52-4)
• EPA Substance Registry System: Benzenamine, 2-ethynyl-N,N-dimethyl-(219605-52-4)

Safety Data

• Hazardous Substances Data: 219605-52-4(Hazardous Substances Data)

Upstream product

• 698-00-0 2-bromo-N,N-dimethylaniline 
• 698-02-2 N,N-dimethyl-o-iodoaniline 
• 219605-51-3 N,N-dimethyl-2-((trimethylsilyl)ethynyl)benzenamine 

Downstream Products

• 54655-08-2 N,N-dimethyl-2-(2-phenylethynyl)aniline 
• 736184-67-1 2-{[2-(N,N-dimethylamino)phenyl]ethynyl}aniline 
• 588699-93-8 ethyl 2-[[(2-dimetylamino)phenyl]ethynyl]-1-cyclopentenecarboxylate 
• 1401560-14-2 N,N-dimethyl-2-(naphthalen-1-ylethynyl)aniline 
• 1094425-25-8 N,N-dimethyl-2-[(2-methoxyphenyl)ethynyl]aniline 
• 62167-04-8 2-((4-methoxyphenyl)ethynyl)-N,N-dimethylaniline 
• 54655-09-3 N,N-dimethyl-2-(4-methylphenylethynyl)aniline 

Relevant articles and documents

Iodocyclisation of Electronically Resistant Alkynes: Synthesis of 2-Carboxy (and sulfoxy)-3-iodobenzo[ b ]thiophenes

The iodocyclisation of alkynes bearing tethered nucleophiles is a highly effective method for the construction and diversification of heterocycles. A key limitation to this methodology is the 5-endo-dig iodocyclisation of alkynes that have an unfavourable electronic bias for electrophilic cyclisation. These tend to direct electrophilic attack of the iodonium atom to the wrong carbon for cyclisation, thus favouring competing addition reactions. Using our previously determined reaction conditions for the 5-endo-dig iodocyclisations of electronically resistant alkynes, we have achieved efficient synthetic access to 2-carboxy (and sulfoxy)-3-iodobenzo[b]thiophenes. The corresponding benzo[b]furans and indoles were not accessible under these conditions. This difference may arise due to the availability of a radical mechanism in the case of iodobenzo[b]thiophenes. The 2-carboxy functionality of the iodocyclised products can be further employed in iterative alkyne-coupling iodocyclisation reactions, where the carboxy group or an imine (Schiff base) partakes in a second iodocyclisation to generate a lactone or pyridine ring.

Intramolecular Addition of a Dimethylamino C(sp 3)-H Bond across C-C Triple Bonds Using IrCl(DTBM-SEGPHOS)(ethylene) Catalyst: Synthesis of Indoles from 2-Alkynyl- N -methylanilines

Intramolecular addition of a C(sp 3)-H bond of the dimethylamino group across the C-C triple bond in 2-alkynyl- N, N -dimethylanilines is effectively catalyzed by a new iridium complex, IrCl(DTBM-SEGPHOS)(C 2H 4), in mesitylene at 150 °C. The intramolecular C(sp 3)-H addition is followed by double-bond isomerization to afford 3-substituted indoles in good to high yields.

Pd-Catalyzed Indolization/peri-C–H Annulation/N-Dealkylation Cascade to Cyclopenta-Fused Acenaphtho[1,2-b]indole Scaffold

A novel Pd-catalyzed cascade reaction of N,N-dialkyl-substituted o-alkynylanilines involving an indolization/peri-C–H annulation/N-dealkylation sequence has been developed to construct a cyclopenta-fused acenaphtho[1,2-b]indole (ANI) scaffold. A variety of aromatic hydrocarbons having a peri-C–H bond at the alkynyl terminus, such as naphthalene, phenanthrene, pyrene, and fluoranthene, were employed, affording the corresponding π-extended ANI derivatives. The ANI molecules showed relatively narrow energy gaps by increasing HOMOs and lowering LUMOs, implying their potential applications as π-segments in low-band-gap materials.