1-(2-Propenyl)-1a,9b-dihydro-1H-phenanthro(9,10-b)azirine

Base Information

• Chemical Name: 1-(2-Propenyl)-1a,9b-dihydro-1H-phenanthro(9,10-b)azirine
• CAS No.: 91540-30-6
• Deprecated CAS: 101912-69-0
• Molecular Formula: C₁₇H₁₅N
• Molecular Weight: 233.313
• DSSTox Substance ID: DTXSID30906804
• Mol file: 91540-30-6.mol

Synonyms:N-(2-Propenyl)phenanthrene 9,10-imine;91540-30-6;CCRIS 2135;N-Allylphenanthreneimine;BRN 4679022;1-(2-Propenyl)-1a,9b-dihydro-1H-phenanthro(9,10-b)azirine;1H-Phenanthro(9,10-b)azirine, 1a,9b-dihydro-1-(2-propenyl)-;DTXSID30906804;1a,9b-Dihydro-1-(2-propen-1-yl)-1H-phenanthro[9,10-b]azirine

Chemical Property of 1-(2-Propenyl)-1a,9b-dihydro-1H-phenanthro(9,10-b)azirine

Chemical Property:

• Vapor Pressure: 5.63E-05mmHg at 25°C
• Boiling Point: 346.8°Cat760mmHg
• Flash Point: 148°C
• Density: 1.137g/cm³
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 233.120449483
• Heavy Atom Count: 18
• Complexity: 309

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CCN1C2C1C3=CC=CC=C3C4=CC=CC=C24

Technology Process of 1-(2-Propenyl)-1a,9b-dihydro-1H-phenanthro(9,10-b)azirine

There total 6 articles about 1-(2-Propenyl)-1a,9b-dihydro-1H-phenanthro(9,10-b)azirine 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: 66.0%

1a,9b-dihydro-1H-phenanthro<9,10-b>azirine (74684-57-4) + 3-chloroprop-1-ene (107-05-1) → 1-(2-propenyl)-1a,9b-dihydrophenanthro<9,10-b>azirine (91540-30-6)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; for 48h; Heating;

Reference yield:

trans-9-azido-10-chloro-9,10-dihydrophenanthrene → N-(2-propenyl)phenanthrene 9,10-imine (91540-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

2: 50percent aq. NaOH/triethylbenzylammonium chloride / CH₂Cl₂

With sodium hydroxide; lithium aluminium tetrahydride; N-benzyl-N,N,N-triethylammonium chloride; In tetrahydrofuran; dichloromethane;

Reference yield:

(+/-)-trans-9-Azido-10-hydroxy-9,10-dihydrophenanthrene (53581-32-1) → N-(2-propenyl)phenanthrene 9,10-imine (91540-30-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 38 percent / SOCl₂ / benzene / 48 h / Ambient temperature

2: LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

3: 50percent aq. NaOH/triethylbenzylammonium chloride / CH₂Cl₂

With sodium hydroxide; lithium aluminium tetrahydride; thionyl chloride; N-benzyl-N,N,N-triethylammonium chloride; In tetrahydrofuran; dichloromethane; benzene;

upstream raw materials:

1a,9b-dihydro-1H-phenanthro<9,10-b>azirine

3-chloroprop-1-ene

(+/-)-trans-9-Azido-10-hydroxy-9,10-dihydrophenanthrene

1a,9b-dihydro-1H-phenanthro<9,10-b>azirine

Refernces

• 1、 Shtelzer, Sarah,Weitzberg, Moshe,Jeries, Juliette,Sheradsky, Tuvia,Aizenshtat, Zeev,Blum, Jochanan. "The Chemistry of Polycyclic Arene Imines. III. N-Alkylation of Phenanthrene 9,10-Imine ". . p. 1 - 3. Retrieved 2007/10/02.