1-[4-(Trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane-2,4-dione

Base Information

• Chemical Name: 1-[4-(Trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane-2,4-dione
• CAS No.: 66504-22-1
• Molecular Formula: C12H8F3NO2
• Molecular Weight: 255.196
• DSSTox Substance ID: DTXSID80507961
• Mol file: 66504-22-1.mol

Synonyms:1-[4-(Trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane-2,4-dione;66504-22-1;SCHEMBL2056307;DTXSID80507961;IMGFNMIDWIQJDG-UHFFFAOYSA-N

Chemical Property of 1-[4-(Trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane-2,4-dione

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 255.05071298
• Heavy Atom Count: 18
• Complexity: 412

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2C1(C(=O)NC2=O)C3=CC=C(C=C3)C(F)(F)F

Technology Process of 1-[4-(Trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane-2,4-dione

There total 5 articles about 1-[4-(Trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane-2,4-dione 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: 30.0%

(1R,2S)-1-(4-Trifluoromethyl-phenyl)-cyclopropane-1,2-dicarboxylic acid (66504-21-0) → 1-(p-trifluoromethylphenyl)-1,2-cyclopropanedicarboximide (66504-22-1)

Guidance literature:

With urea; In xylene; Heating;

DOI:10.1021/jm00137a002

Reference yield:

methyl 2-(4-(trifluoromethyl)phenyl)acetate (135325-18-7) → 1-(p-trifluoromethylphenyl)-1,2-cyclopropanedicarboximide (66504-22-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 39 percent / NBS, 48percent aq. HBr / CCl₄ / Heating

2: 66 percent / NaOMe / diethyl ether / 24 h / Ambient temperature

3: 48 percent / KOH / ethanol; H₂O / 6 h / Heating

4: 30 percent / urea / xylene / Heating

With potassium hydroxide; N-Bromosuccinimide; hydrogen bromide; sodium methylate; urea; In tetrachloromethane; diethyl ether; ethanol; water; xylene;

DOI:10.1021/jm00137a002

Reference yield:

α-bromo-(4-(trifluoromethyl)phenyl)acetic acid methyl ester (77053-53-3) → 1-(p-trifluoromethylphenyl)-1,2-cyclopropanedicarboximide (66504-22-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / NaOMe / diethyl ether / 24 h / Ambient temperature

2: 48 percent / KOH / ethanol; H₂O / 6 h / Heating

3: 30 percent / urea / xylene / Heating

With potassium hydroxide; sodium methylate; urea; In diethyl ether; ethanol; water; xylene;

DOI:10.1021/jm00137a002

upstream raw materials:

(1R,2S)-1-(4-Trifluoromethyl-phenyl)-cyclopropane-1,2-dicarboxylic acid

methyl 2-(4-(trifluoromethyl)phenyl)acetate

α-bromo-(4-(trifluoromethyl)phenyl)acetic acid methyl ester

(1R,2S)-1-(4-Trifluoromethyl-phenyl)-cyclopropane-1,2-dicarboxylic acid dimethyl ester

Downstream raw materials:

1-(p-Trifluoromethylphenyl)-3-azabicyclo[3.1.0]hexane