3-(Triphenyl-lambda~5~-phosphanylidene)cinnolin-4(3H)-one

Base Information

• Chemical Name: 3-(Triphenyl-lambda~5~-phosphanylidene)cinnolin-4(3H)-one
• CAS No.: 109773-41-3
• Molecular Formula: C₂₆H₁₉N₂OP
• Molecular Weight: 406.423
• DSSTox Substance ID: DTXSID30547211
• Wikidata: Q82425289
• Mol file: 109773-41-3.mol

Synonyms:109773-41-3;3-(Triphenylphosphoranylidene)cinnolin-4(3H)-one;SCHEMBL12359258;3-(Triphenyl-lambda~5~-phosphanylidene)cinnolin-4(3H)-one;DTXSID30547211

Chemical Property of 3-(Triphenyl-lambda~5~-phosphanylidene)cinnolin-4(3H)-one

Chemical Property:

• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 406.12350023
• Heavy Atom Count: 30
• Complexity: 644

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(=C2C(=O)C3=CC=CC=C3N=N2)(C4=CC=CC=C4)C5=CC=CC=C5

Technology Process of 3-(Triphenyl-lambda~5~-phosphanylidene)cinnolin-4(3H)-one

There total 8 articles about 3-(Triphenyl-lambda~5~-phosphanylidene)cinnolin-4(3H)-one 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:

(tert-Butoxycarbonylmethylene)triphenylphosphorane (86302-43-4,35000-38-5) → 4-Oxo-3-triphenylphosphoranylidene-3,4-dihydrocinnoline (109773-41-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / benzene / 16 h / Ambient temperature

2: 92 percent / 85percent aq. H₂SO₄ / CH₂Cl₂ / 3 h / Ambient temperature

3: 69 percent / SnCl₂*2H₂O / ethyl acetate / 3 h / Heating

4: n-pentyl nitrite, 36percent aq. HCl / methanol / 0.25 h / 0 °C

5: 10percent aq. NaOH / Ambient temperature

With hydrogenchloride; sodium hydroxide; n-Amyl nitrite; sulfuric acid; tin(ll) chloride; In methanol; dichloromethane; ethyl acetate; benzene;

DOI:10.1055/s-1987-27921

Reference yield:

1-(2-Amino-phenyl)-2-(triphenyl-λ5-phosphanylidene)-ethanone (111054-05-8) → 4-Oxo-3-triphenylphosphoranylidene-3,4-dihydrocinnoline (109773-41-3)

Guidance literature:

Multi-step reaction with 2 steps

1: n-pentyl nitrite, 36percent aq. HCl / methanol / 0.25 h / 0 °C

2: 10percent aq. NaOH / Ambient temperature

With hydrogenchloride; sodium hydroxide; n-Amyl nitrite; In methanol;

DOI:10.1055/s-1987-27921

Reference yield:

1-(2-nitrophenyl)-2-(triphenylphosphoranylidene)ethanone (111054-12-7) → 4-Oxo-3-triphenylphosphoranylidene-3,4-dihydrocinnoline (109773-41-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / SnCl₂*2H₂O / ethyl acetate / 3 h / Heating

2: n-pentyl nitrite, 36percent aq. HCl / methanol / 0.25 h / 0 °C

3: 10percent aq. NaOH / Ambient temperature

With hydrogenchloride; sodium hydroxide; n-Amyl nitrite; tin(ll) chloride; In methanol; ethyl acetate;

DOI:10.1055/s-1987-27921

upstream raw materials:

(tert-Butoxycarbonylmethylene)triphenylphosphorane

1-(2-Amino-phenyl)-2-(triphenyl-λ⁵-phosphanylidene)-ethanone

1-(2-nitrophenyl)-2-(triphenylphosphoranylidene)ethanone

3-(2-Nitro-phenyl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid tert-butyl ester

Downstream raw materials:

(1-Benzyl-4-oxo-1,4-dihydro-cinnolin-3-yl)-triphenyl-phosphonium; bromide

(1-Ethyl-4-oxo-1,4-dihydro-cinnolin-3-yl)-triphenyl-phosphonium; iodide

(4-Oxo-1-propyl-1,4-dihydro-cinnolin-3-yl)-triphenyl-phosphonium; bromide

4(1H)-cinnolon