(E)-1-chloro-3-(1-nitroprop-1-en-2-yl)benzene

Base Information

• Chemical Name: (E)-1-chloro-3-(1-nitroprop-1-en-2-yl)benzene
• CAS No.: 947383-49-5
• Molecular Formula: C₉H₈ClNO₂
• Molecular Weight: 197.621
• Mol file: 947383-49-5.mol

Synonyms:(E)-1-chloro-3-(1-nitroprop-1-en-2-yl)benzene

Chemical Property of (E)-1-chloro-3-(1-nitroprop-1-en-2-yl)benzene

Chemical Property:

Purity/Quality:

95%-98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-chloro-3-(1-nitroprop-1-en-2-yl)benzene

There total 3 articles about (E)-1-chloro-3-(1-nitroprop-1-en-2-yl)benzene 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: 72.0%

3-chloro-α-methylstyrene (1712-71-6) → (E)-1-chloro-3-(1-nitroprop-1-en-2-yl)benzene (947383-49-5)

Guidance literature:

3-chloro-α-methylstyrene; With ammonium cerium (IV) nitrate; sodium nitrite; In chloroform; for 0.25h;

With acetic acid; In chloroform; at 30 ℃;

Reference yield:

nitromethane (75-52-5) + 3'-Chloroacetophenone (99-02-5) → (E)-1-chloro-3-(1-nitroprop-1-en-2-yl)benzene (947383-49-5)

Guidance literature:

With N-butylamine; In toluene; Heating;

DOI:10.1021/ja074045c

Reference yield:

3'-Chloroacetophenone (99-02-5) → (E)-1-chloro-3-(1-nitroprop-1-en-2-yl)benzene (947383-49-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / diethyl ether; hexane / 1 h / Inert atmosphere

1.2: 24 h / 20 °C / Inert atmosphere

2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Inert atmosphere; Sonication

With n-butyllithium; ammonium cerium (IV) nitrate; acetic acid; sodium nitrite; In diethyl ether; hexane; chloroform; 1.2: Wittig reaction;

DOI:10.1002/anie.201202715

upstream raw materials:

nitromethane

3'-Chloroacetophenone

3-chloro-α-methylstyrene

Downstream raw materials:

2-(3-chlorophenyl) propan-1-amine

Lorcaserin hydrochloride

Refernces

• 1、 Sim, Jae Hun,Song, Choong Eui. "Water-Enabled Catalytic Asymmetric Michael Reactions of Unreactive Nitroalkenes: One-Pot Synthesis of Chiral GABA-Analogs with All-Carbon Quaternary Stereogenic Centers". supporting information. p. 1835 - 1839. Retrieved 2017/02/05.
• 2、 Bertolotti, Mattia,Brenna, Elisabetta,Crotti, Michele,Gatti, Francesco G.,Monti, Daniela,Parmeggiani, Fabio,Santangelo, Sara. "Substrate Scope Evaluation of the Enantioselective Reduction of β-Alkyl-β-arylnitroalkenes by Old Yellow Enzymes 1-3 for Organic Synthesis Applications". . p. 577 - 583. Retrieved 2016/02/23.