alpha-Diazo-4'-chloroacetophenone

Base Information

• Chemical Name: alpha-Diazo-4'-chloroacetophenone
• CAS No.: 3282-33-5
• Molecular Formula: C8H5 Cl N2 O
• Molecular Weight: 180.593
• NSC Number: 254953
• DSSTox Substance ID: DTXSID40954477
• Nikkaji Number: J2.294.266B,J354.177K
• Mol file: 3282-33-5.mol

Synonyms:3282-33-5;DTXSID40954477;alpha-Diazo-4'-chloroacetophenone;1-(4-chlorophenyl)-2-diazoethanone;NSC254953;1-(4-chlorophenyl)-2-diazo-ethanone;AKOS023430321;NSC-254953;1-(4-Chloro-phenyl)-2-diazo-ethanone;1-(4-Chlorophenyl)-2-diazoethan-1-one;1-Diazonio-2-oxo-2-(4-chlorophenyl)ethane-1-ide

Chemical Property of alpha-Diazo-4'-chloroacetophenone

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 180.0090405
• Heavy Atom Count: 12
• Complexity: 215

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)C=[N+]=[N-])Cl

Technology Process of alpha-Diazo-4'-chloroacetophenone

There total 16 articles about alpha-Diazo-4'-chloroacetophenone 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: 98.0%

1,3-bis(4-chlorophenyl)propane-1,3-dione (18362-49-7) → 1-(4-chlorophenyl)-2-diazoethanone (3282-33-5)

Guidance literature:

With 4-toluenesulfonyl azide; methylamine; In ethanol; water; at 20 ℃; for 0.166667h;

DOI:10.1021/acs.joc.7b01187

Reference yield: 97.0%

C8H6Cl2N2O (277298-60-9) → 1-(4-chlorophenyl)-2-diazoethanone (3282-33-5)

Guidance literature:

With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃; for 8h;

Reference yield: 95.0%

1-(4-chloro-phenyl)-2,2-dihydroxy-ethanone (4996-21-8) → 1-(4-chlorophenyl)-2-diazoethanone (3282-33-5)

Guidance literature:

With caesium carbonate; toluene-4-sulfonic acid hydrazide; In chloroform; at 20 ℃; for 0.0833333h;

DOI:10.1016/j.tet.2014.10.044

upstream raw materials:

diazomethane

4-chloro-benzoyl chloride

para-chlorobenzoic acid

sodium salt of ω-formyl-4-chloroacetophenone

Downstream raw materials:

2-(4-chlorophenyl)-1-methyl-2-phenyl-1H-indole

3-(4-chlorophenyl)-1-methyl-1H-indole

1-ethyl-3-(4-chloro-phenyl)-indole

2-(4-chlorophenyl)-N-hydroxy-2-oxoethanimidoyl chloride

Refernces

• 1、 Suneja, Arun,Schneider, Christoph. "Phosphoric Acid Catalyzed [4 + 1]-Cycloannulation Reaction of ortho-Quinone Methides and Diazoketones: Catalytic, Enantioselective Access toward cis-2,3-Dihydrobenzofurans". supporting information. p. 7576 - 7580. Retrieved 2019/01/03.
• 2、 Zhang, Jianlan,Chen, Wenwen,Huang, Dayun,Zeng, Xiaobao,Wang, Xinyan,Hu, Yuefei. "Tandem Synthesis of α-Diazoketones from 1,3-Diketones". . p. 9171 - 9174. Retrieved 2017/09/11.