2-[4-(2-Aminophenyl)buta-1,3-diynyl]aniline

Base Information

• Chemical Name: 2-[4-(2-Aminophenyl)buta-1,3-diynyl]aniline
• CAS No.: 31661-58-2
• Molecular Formula: C16H12N2
• Molecular Weight: 232.285
• NSC Number: 729466
• DSSTox Substance ID: DTXSID30372782
• Nikkaji Number: J802.550I
• Wikidata: Q82160657
• Mol file: 31661-58-2.mol

Synonyms:31661-58-2;2-[4-(2-aminophenyl)buta-1,3-diynyl]aniline;2,2'-(Buta-1,3-diyne-1,4-diyl)dianiline;Benzenamine, 2,2'-(1,3-butadiyne-1,4-diyl)bis-;YSZC1998;2,2'-diaminodiphenyldiacetylene;DTXSID30372782;NSC729466;NSC-729466;1,4-Bis(2-aminophenyl)-1,3-butadiyne;CS-0379108;F21321

Chemical Property of 2-[4-(2-Aminophenyl)buta-1,3-diynyl]aniline

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 232.100048391
• Heavy Atom Count: 18
• Complexity: 360

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C#CC#CC2=CC=CC=C2N)N

Technology Process of 2-[4-(2-Aminophenyl)buta-1,3-diynyl]aniline

There total 7 articles about 2-[4-(2-Aminophenyl)buta-1,3-diynyl]aniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2-ethynylaniline (52670-38-9) → 2-[4-(2-aminophenyl)-1,3-butadienyl]phenylamine (31661-58-2)

Guidance literature:

With piperidine; In tetrahydrofuran; at 65 ℃; for 14h;

DOI:10.1002/ejoc.201001735

Reference yield: 79.0%

2-iodophenylamine (615-43-0) + trimethylsilylacetylene (1066-54-2) → 2-[4-(2-aminophenyl)-1,3-butadienyl]phenylamine (31661-58-2)

Guidance literature:

2-iodophenylamine; trimethylsilylacetylene; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

With methanol; potassium carbonate; at 20 ℃; for 2h; Inert atmosphere;

With pyridine; copper(II) acetate monohydrate; In methanol; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/anie.202004049

Reference yield: 54.0%

2-[(trimethylsilyl)ethynyl]aniline (103529-16-4) + 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl bromide (71528-62-6,4196-35-4,53081-30-4,67145-38-4,67773-43-7,95189-56-3,103618-17-3,148905-25-3) → 2-[4-(2-aminophenyl)-1,3-butadienyl]phenylamine (31661-58-2) + 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-(o-aminophenyl)-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-mann-octitol + 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-(o-aminophenyl)-1,1,2,2-tetradehydro-1,2-dideoxy-D-glycero-D-mann-octitol

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; In triethylamine; N,N-dimethyl-formamide; at 20 ℃; for 12h;

upstream raw materials:

bis-(2-acetylamino-phenyl)-butadiyne

2-ethynylaniline

2-[(trimethylsilyl)ethynyl]aniline

2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl bromide

Downstream raw materials:

2,2,2-trifluoro-N-(2-(4-[2,2,2-trifluoro-acetylamino-phenyl]-buta-1,3-diynyl)-phenyl)-acetamide

C₅₂H₃₈N₂P₂

C₃₂H₂₆N₄O₂

bis-(2-acetylamino-phenyl)-butadiyne

Refernces

Bis(heterocumulenes) derived from the 1,4-diphenyl-1,3-butadiyne framework. Synthesis of three new classes of axially chiral biheteroaryls

10.1021/jo7021058

The research focuses on the synthesis of three new classes of axially chiral biheteroaryls derived from the 1,4-diphenyl-1,3-butadiyne framework. The purpose of the study was to explore the reactivity of bis(ketenimines) and bis(carbodiimides) and their potential to form axially chiral bis(benzocarbazoles) and bis(quinindolines) through biradical cyclizations. The researchers successfully prepared these compounds, as well as mixed biheteroaryls consisting of benzocarbazole and quinindoline units, using a modified strategy. The chemicals used in the process included 1,4-bis(2-aminophenyl)-1,3-butadiynes, diphenylketene, triphenylphosphine, carbon tetrachloride, triethylamine, arylisothiocyanates, and various aryl isocyanates. The conclusions of the research were that the bis(heterocumulenes) could undergo simultaneous biradical cyclization leading to potential tetraradicaloid intermediates, and that the resulting compounds were obtained as racemic mixtures of atropoenantiomers due to the presumed chiral biaryl axis.