324740-69-4

Basic information

• Product Name: 2-[4-(N,N-dimethylamino)phenyl]-1H-pyrrole
• Synonyms: 2-[4-(N,N-dimethylamino)phenyl]-1H-pyrrole
• CAS NO: 324740-69-4
• Molecular Weight: 186.257
• Mol File: 324740-69-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-[4-(N,N-dimethylamino)phenyl]-1H-pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[4-(N,N-dimethylamino)phenyl]-1H-pyrrole(324740-69-4)
• EPA Substance Registry System: 2-[4-(N,N-dimethylamino)phenyl]-1H-pyrrole(324740-69-4)

Safety Data

• Hazardous Substances Data: 324740-69-4(Hazardous Substances Data)

Upstream product

• 109-97-7 pyrrole 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 586-77-6 4-bromo-N,N-dimethylaniline 
• 2124-31-4 4'-dimethylaminoacetophenone 
• 6310-87-8 p-dimethylaminoacetophenone oxime 
• 75-20-7 calcium carbide 
• 187672-34-0 4-dimethylaminoacetophenone oxime 
• 74-86-2 acetylene 
• 1159490-62-6 4-dimethylaminoacetophenone O-vinyloxime 

Relevant articles and documents

Isomer-Specific Hydrogen Bonding as a Design Principle for Bidirectionally Quantitative and Redshifted Hemithioindigo Photoswitches

A new class of bidirectionally quantitative photoswitches based on the hemithioindigo (HTI) scaffold is reported. Incorporation of a pyrrole hydrogen-bond donor leads to a bathochromic shift allowing for quantitative bidirectional isomerization. Additionally, extending conjugation from the electron-rich pyrrole results in quantitative visible-light photoswitches, as well as photoswitches that isomerize with red and near-infrared light. The presence of the hydrogen bond leading to the observed redshift is supported by computational and spectroscopic evidence.

4-Dimethylaminoacetophenone O-vinyloxime: Synthesis and steric structure

4-Dimethylaminoacetophenone oxime was synthesized from 4- dimethylaminoacetophenone and hydroxylamine hydrochloride. Its reaction with acetylene in the system KOH-DMSO gave previously unknown 4- dimethylaminoacetophenone O-vinyloxime as the major product.

Generation and reactivity of the 4-aminophenyl cation by photolysis of 4-chloroaniline

4-Chloroaniline and its N,N-dimethyl derivative are photostable in cyclohexane but undergo efficient photoheterolysis in polar media via the triplet state and give the corresponding triplet phenyl cations. CASSCF and UB3LYP calculations show that the 4-aminophenyl triplet cation has a planar geometry and is stabilized by > 10 kcal mol-1 with respect to the slightly bent singlet. The triplet has a mixed carbene-diradical character at the divalent carbon. This species either adds to the starting substrate forming 5-chloro-2,4′-diaminodiphenyls (via an intermediate cyclohexadienyl cation) or is reduced to the aniline (via the aniline radical cation) in a ratio depending on the hydrogen-donating properties of the solvent. Transients attributable to the triplet aminophenyl cation as well as to the ensuing intermediates are detected. Chemical evidence for the generation of the phenyl cation is given by trapping via electrophilic substitution with benzene, mesitylene, and hexamethylbenzene (in the last case the main product is a 6-aryl-3-methylene-1,4-cyclohexadiene). Relative rates of electrophilic attack to benzene and to some alkenes and five-membered heterocycles are measured and span over a factor of 15 or 30 for the two cations. The triplet cation formed under these conditions is trapped by iodide more efficiently than by the best π nucleophiles, However, in contrast to the singlet cation, it does not form ethers with alcohols, by which it is rather reduced.