Chemistry Heterocyclic Building Blocks Thiophenes N,N-Diphenyl-4-(Thiophen-2-Yl)Aniline

N,N-Diphenyl-4-(Thiophen-2-Yl)Aniline

Aromatic Substitution: The phenyl rings in the molecule are susceptible to electrophilic aromatic substitution reactions, such as nitration, halogenation, or Friedel-Crafts reactions. For example, you can nitrate the phenyl rings to introduce nitro groups. Reduction of Nitro Groups: If nitro groups are introduced into the molecule through nitration, they can be reduced to amino groups using reducing agents like hydrogen and a catalyst (e.g., palladium on carbon) or other methods like the Clemmensen reduction or the Wolff-Kishner reduction. Heterocycle Formation: The thiophene ring can participate in various heterocyclic reactions, such as the synthesis of thiophene derivatives through condensation reactions with appropriate reagents. Nucleophilic Aromatic Substitution: The amino group can act as a nucleophile in nucleophilic aromatic substitution (SNAr) reactions, potentially leading to the substitution of the thiophene ring or the phenyl rings with various electrophilic groups. Hofmann Rearrangement: The amine group can undergo the Hofmann rearrangement when treated with chloroform and a strong base, leading to the formation of an isocyanate derivative. Cross-Coupling Reactions: The molecule can participate in various cross-coupling reactions, such as Suzuki-Miyaura or Heck reactions, to form biaryl or other aryl-aryl linked compounds. Hydrogenation: The unsaturated bonds in the molecule can be hydrogenated using a hydrogen source and a suitable catalyst to reduce double bonds or aromatic rings to saturated counterparts. Nucleophilic Addition: Depending on the reaction conditions, the molecule may undergo nucleophilic addition reactions with electrophiles, such as aldehydes or ketones, at the amino or thiophene groups.

Further Reading:

Framework+−

(9H-Fluoren-9-Yl)Methyl (2-(Thiophen-2-Yl)Ethyl)Carbamate 1-(Thiophen-2-Yl)Ethan-1-One 2,2'-Bithiophene 2,2':5',2''-Terthiophene 2,3-Dihydrothieno[3,4-B][1,4]Dioxine 2,5-Dibromothiophene 2,5-Diphenylthiophene 2-(Thiophen-2-Yl)Pyridine 2-(Trifluoromethyl)Thiophene 2-Chlorothiophene 2-Ethynylthiophene 2-Iodothiophene 2-Methoxythiophene 2-Nitrothiophene 3-Bromothiophene 3-Chlorothiophene 3-Fluorothiophene 3-Methoxythiophene 3-Methylthiophene 3-Nitrothiophene 3-Phenylthiophene 4,4,5,5-Tetramethyl-2-(Thiophen-2-Yl)-1,3,2-Dioxaborolane 4,4,5,5-Tetramethyl-2-(Thiophen-3-Yl)-1,3,2-Dioxaborolane 4,5,6,7-Tetrahydrothieno[2,3-C]Pyridine 4,5,6,7-Tetrahydrothieno[3,2-C]Pyridine 4,7-Di(Thiophen-2-Yl)Benzo[C][1,2,5]Thiadiazole 4,8-Di(Thiophen-2-Yl)Benzo[1,2-B:4,5-B']Dithiophene 4-Phenyl-6H-Thieno[3,2-F][1,2,4]Triazolo[4,3-A][1,4]Diazepine 4H-Cyclopenta[2,1-B:3,4-B']Dithiophene 4H-Thieno[3,2-B]Pyrrole 4H-Thieno[3,4-C]Pyrrole-4,6(5H)-Dione 5,6-Dihydro-4H-Cyclopenta[B]Thiophene 5-(Thiophen-2-Yl)Isoxazole 5-Benzyl-4,5,6,7-Tetrahydrothieno[3,2-C]Pyridine 5-Phenylthiophen-2-Amine Benzo[1,2-B:4,5-B']Dithiophene Dibenzo[B,D]Thiophene Dihydrothiophen-3(2H)-One Dithieno[3,2-B:2',3'-D]Thiophene Ethyl Thiophene-2-Carboxylate Ethyl Thiophene-3-Carboxylate Methyl Thiophene-3-Carboxylate N,N-Diphenyl-4-(Thiophen-2-Yl)Aniline Phenyl(Thiophen-2-Yl)Methanone Thieno[2,3-B]Pyridine Thieno[2,3-C]Pyridine Thieno[2,3-D]Pyrimidine Thieno[3,2-B]Pyridine Thieno[3,2-B]Thiophene Thieno[3,2-C]Pyridine Thieno[3,2-D]Pyrimidine Thieno[3,4-B]Thiophene Thiophen-2-Ylboronic Acid Thiophen-2-Ylmethanol Thiophen-3-Amine Thiophen-3-Ol Thiophene-2-Carbaldehyde Thiophene-2-Carbonitrile Thiophene-3-Carbaldehyde Thiophene-3-Carbonitrile Thiophene-3-Carboxamide Thiophene-3-Carboxylic Acid

By Key Group+−

Acetylthiophene Aminothiophene Bromothieno Chlorothieno Chlorothiophene Cyanothiophene Dibromothieno Dibromothiophene Dichlorothieno Dichlorothiophene Dihydrothieno Dihydrothiophene Dihydroxythiophene Dimethylthieno Dimethylthiophene Dithiophene Fluorothiophene Formylthiophene Hydroxythiophene Iodothieno Iodothiophene Methylthieno Nitrothiophene Oxotetrahydrothiophene Terthiophene Tetrahydrothieno Thiophen-Amine-Hydrochloride Thiophenecarboxaldehyde Thiphen-Amine-Hydrochloride Trithiophene

By Route Intermediates+−

cLogP+−

H-Acceptors+−

H-Donors+−

Polar Surface Area+−

Druglikeness+−

NNCH/NNH+−

sp3-Atoms+−

Non-Aromatic Rings+−

Aromatic Rings+−

Rotatable Bonds+−

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