2,3-Bis(4-{[1-(naphthalen-1-yl)cyclohexa-2,4-dien-1-yl]amino}phenyl)but-2-enedinitrile

Base Information

• Chemical Name: 2,3-Bis(4-{[1-(naphthalen-1-yl)cyclohexa-2,4-dien-1-yl]amino}phenyl)but-2-enedinitrile
• CAS No.: 638222-73-8
• Molecular Formula: C₄₈H₃₂N₄
• Molecular Weight: 664.809
• DSSTox Substance ID: DTXSID70700227
• Mol file: 638222-73-8.mol

Synonyms:DTXSID70700227;2,3-Bis(4-{[1-(naphthalen-1-yl)cyclohexa-2,4-dien-1-yl]amino}phenyl)but-2-enedinitrile;638222-73-8

Chemical Property of 2,3-Bis(4-{[1-(naphthalen-1-yl)cyclohexa-2,4-dien-1-yl]amino}phenyl)but-2-enedinitrile

Chemical Property:

• XLogP3: 11.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 668.29399717
• Heavy Atom Count: 52
• Complexity: 1380

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C=CC=CC1(C2=CC=CC3=CC=CC=C32)NC4=CC=C(C=C4)C(=C(C#N)C5=CC=C(C=C5)NC6(CC=CC=C6)C7=CC=CC8=CC=CC=C87)C#N

Technology Process of 2,3-Bis(4-{[1-(naphthalen-1-yl)cyclohexa-2,4-dien-1-yl]amino}phenyl)but-2-enedinitrile

There total 2 articles about 2,3-Bis(4-{[1-(naphthalen-1-yl)cyclohexa-2,4-dien-1-yl]amino}phenyl)but-2-enedinitrile 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: 50.0%

N-phenyl-1-naphthylamine (90-30-2) + (2E)-2,3-bis(4-bromophenyl)-2-butenedinitrile (82193-93-9) → bis{4-[N-(1-naphthyl)phenylamino]phenyl}fumaronitrile (638222-73-8)

Guidance literature:

With tri-tert-butyl phosphine; caesium carbonate; palladium diacetate; In toluene; at 110 ℃; for 24h;

DOI:10.1039/b309780c

Reference yield:

4-Bromophenylacetonitrile (16532-79-9) → bis{4-[N-(1-naphthyl)phenylamino]phenyl}fumaronitrile (638222-73-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / I₂; NaOMe / methanol; diethyl ether / 4.5 h / -78 - 0 °C

2: 50 percent / Cs₂CO₃; P(t-Bu)3 / Pd(OAc)2 / toluene / 24 h / 110 °C

With tri-tert-butyl phosphine; iodine; sodium methylate; caesium carbonate; palladium diacetate; In methanol; diethyl ether; toluene;

DOI:10.1039/b309780c

upstream raw materials:

N-phenyl-1-naphthylamine

(2E)-2,3-bis(4-bromophenyl)-2-butenedinitrile

4-Bromophenylacetonitrile