Diazoacetophenone

Base Information

• Chemical Name: Diazoacetophenone
• CAS No.: 3282-32-4
• Molecular Formula: C8H6N2O
• Molecular Weight: 146.148
• Hs Code.: 2927000090
• NSC Number: 25280
• DSSTox Substance ID: DTXSID80954476
• Nikkaji Number: J2.294.264F,J80.679J
• Mol file: 3282-32-4.mol

Synonyms:Diazoacetophenone;2-Diazo-1-phenylethanone;3282-32-4;Phenyl diazomethyl ketone;2-Diazo-1-phenylethan-1-one;2-Diazoacetophenone;Diazomethyl phenyl ketone;alpha-Diazoacetophenone;Ethanone, 2-diazo-1-phenyl-;ACETOPHENONE, 2-DIAZO-;.alpha.-Diazoacetophenone;.omega.-Diazoacetophenone;NSC 25280;2-diazo-1-phenyl-ethanone;BRN 1636122;4-07-00-02133 (Beilstein Handbook Reference);(E)-2-diazonio-1-phenylethenolate;DTXSID80954476;NSC25280;(E)-2-diazonio-1-phenyl-ethenolate;NSC-25280;AKOS015917546;AT25592;1-Diazonio-2-oxo-2-phenylethane-1-ide;EN300-76953;A821442

Chemical Property of Diazoacetophenone

Chemical Property:

• Melting Point: 49 °C
• Refractive Index: 1.4900 (estimate)
• Boiling Point: 265.75°C (rough estimate)
• PSA: 54.46000
• Density: 1.2312 (rough estimate)
• LogP: 1.25096
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 146.048012819
• Heavy Atom Count: 11
• Complexity: 188

Purity/Quality:

99%, ^*data from raw suppliers

2-DIAZO-1-PHENYLETHANONE 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Diazoacetophenone

There total 62 articles about Diazoacetophenone 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: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + benzoyl chloride (98-88-4) → 2-diazo-acetophenone (3282-32-4)

Guidance literature:

With calcium oxide; In diethyl ether; at 0 ℃; for 3.08333h;

DOI:10.1021/jo101105g

Reference yield: 98.0%

1,3-diphenylpropanedione (120-46-7,61346-73-4) → 2-diazo-acetophenone (3282-32-4)

Guidance literature:

With 4-toluenesulfonyl azide; methylamine; In ethanol; water; at 20 ℃; for 0.416667h; Reagent/catalyst; Solvent;

DOI:10.1021/acs.joc.7b01187

Reference yield: 95.0%

α-bromoacetophenone (70-11-1) → 2-diazo-acetophenone (3282-32-4)

Guidance literature:

With N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 0.333333h; Cooling with ice;

DOI:10.1021/jo5011312

upstream raw materials:

diazomethane

Benzoyl bromide

diethyl ether

benzoyl chloride

Downstream raw materials:

1,3,4,4-tetraphenyl-azetidin-2-one

N-(4-chloro-benzoyl)-2-diazo-3-oxo-3-phenyl-propionamide

2-isopropyl-5-phenyloxazole

cis-2,3-diphenyl-1-benzoylcyclopropane

Refernces

• 1、 Mykhailiuk, Pavel K.. "Three-component synthesis of fluorinated pyrazoles from fluoroalkylamines, NaNO2 and electron-deficient alkynes". . p. 3438 - 3445. Retrieved 2015.
• 2、 Fenwick et al.. "-". . p. 124,128, 130. Retrieved 1973.
• 3、 Lu, Guan-Han,Huang, Tzu-Chia,Hsueh, Hsiao-Chin,Yang, Shin-Cherng,Cho, Ting-Wei,Chou, Ho-Hsuan. "NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds". supporting information. p. 4839 - 4842. Retrieved 2021/05/25.
• 4、 Alegre-Requena, Juan V.,De Lescure, Louis,Modak, Atanu,Paton, Robert S.,Race, Nicholas J.,Rynders, Kathryn J.. "Homologation of Electron-Rich Benzyl Bromide Derivatives via Diazo C-C Bond Insertion". supporting information. . Retrieved 2021/12/27.