3-Azabicyclo[3.1.0]hexane-2,4-dione,1-(4-chlorophenyl)-

Base Information

• Chemical Name: 3-Azabicyclo[3.1.0]hexane-2,4-dione,1-(4-chlorophenyl)-
• CAS No.: 66537-94-8
• Molecular Formula: C11H8 Cl N O2
• Molecular Weight: 221.643
• Mol file: 66537-94-8.mol

Synonyms:3-Azabicyclo[3.1.0]hexane-2,4-dione,1-(4-chlorophenyl)-, (?à)-; 1-(p-Chlorophenyl)-1,2-cyclopropanedicarboximide; CL 53415;Ciproximide; Cyproximide

Chemical Property of 3-Azabicyclo[3.1.0]hexane-2,4-dione,1-(4-chlorophenyl)-

Chemical Property:

• Melting Point: 172-173 °C(Solv: ethanol (64-17-5))
• Boiling Point: 418.4°Cat760mmHg
• PKA: 11.10±0.40(Predicted)
• Flash Point: 206.8°C
• PSA: 46.17000
• Density: 1.503g/cm³
• LogP: 1.58290

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Azabicyclo[3.1.0]hexane-2,4-dione,1-(4-chlorophenyl)-

There total 5 articles about 3-Azabicyclo[3.1.0]hexane-2,4-dione,1-(4-chlorophenyl)- 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: 85.0%

(1R,2S)-1-(4-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid (56695-75-1,56695-76-2,66503-90-0) → 1-(p-chlorophenyl)-1,2-cyclopropanedicarboximide (66537-94-8,15518-76-0)

Guidance literature:

With urea; In xylene; Heating;

DOI:10.1021/jm00137a002

Reference yield:

ethyl 2-bromo-2-(4-chlorophenyl)acetate (5445-25-0) → 1-(p-chlorophenyl)-1,2-cyclopropanedicarboximide (66537-94-8,15518-76-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 48 percent / NaOEt / diethyl ether / 24 h / Ambient temperature

2: 54 percent / KOH / ethanol; H₂O / 6 h / Heating

3: 85 percent / urea / xylene / Heating

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

DOI:10.1021/jm00137a002

Reference yield:

4-chloro-benzeneacetic acid, ethyl ester (14062-24-9) → 1-(p-chlorophenyl)-1,2-cyclopropanedicarboximide (66537-94-8,15518-76-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / NBS, 48percent aq. HBr / CCl₄ / Heating

2: 48 percent / NaOEt / diethyl ether / 24 h / Ambient temperature

3: 54 percent / KOH / ethanol; H₂O / 6 h / Heating

4: 85 percent / urea / xylene / Heating

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

DOI:10.1021/jm00137a002

upstream raw materials:

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

ethyl 2-bromo-2-(4-chlorophenyl)acetate

4-chloro-benzeneacetic acid, ethyl ester

(1S,2R)-1-(4-Chloro-phenyl)-cyclopropane-1,2-dicarboxylic acid diethyl ester

Downstream raw materials:

1-(p-chlorophenyl)-4-ethyl-4-hydroxy-3-azabicyclo[3.1.0]hexan-2-one

(-)-1-(p-Chlorophenyl)-3-azabicyclo[3.1.0]hexane hydrochloride

1-(4-chloro-phenyl)-3-methyl-3-aza-bicyclo[3.1.0]hexane

N-methyl-1-(4-chlorophenyl)-1,2-cyclopropanedicarboxamide

Refernces

• 1、 Epstein, Joseph W.,Brabander, Herbert J.,Fanshawe, William J.,Hofmann, Corris M.,McKenzie, Thomas C.,et al.. "1-Aryl-3-azabicyclohexanes, a New Series of Nonnarcotic Analgesic Agents". . p. 481 - 490. Retrieved 2007/10/02.