4-Acetyl-2'-nitrobiphenyl

Base Information

• Chemical Name: 4-Acetyl-2'-nitrobiphenyl
• CAS No.: 5730-96-1
• Molecular Formula: C14H11 N O3
• Molecular Weight: 241.246
• European Community (EC) Number: 227-235-3
• NSC Number: 86936
• DSSTox Substance ID: DTXSID10205923
• Nikkaji Number: J22.001I
• Wikidata: Q83079659
• Mol file: 5730-96-1.mol

Synonyms:4-Acetyl-2'-nitrobiphenyl;5730-96-1;1-(2'-NITRO[1,1'-BIPHENYL]-4-YL)ETHAN-1-ONE;1-(2'-Nitro(1,1'-biphenyl)-4-yl)ethan-1-one;Acetophenone, 4'-(o-nitrophenyl)-;EINECS 227-235-3;Ethanone, 1-(2'-nitro(1,1'-biphenyl)-4-yl)-;Ethanone, 1-(2'-nitro[1,1'-biphenyl]-4-yl)-;NSC86936;2'-Nitro-4-acetylbiphenyl;2-Nitro-4'-acetylbiphenyl;NCIOpen2_005209;SCHEMBL9310402;DTXSID10205923;NSC 86936;NSC-86936

Chemical Property of 4-Acetyl-2'-nitrobiphenyl

Chemical Property:

• Boiling Point: 386.2°Cat760mmHg
• Flash Point: 181.6°C
• PSA: 62.89000
• Density: 1.217g/cm³
• LogP: 3.98760
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 241.07389321
• Heavy Atom Count: 18
• Complexity: 316

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC=C(C=C1)C2=CC=CC=C2[N+](=O)[O-]

Technology Process of 4-Acetyl-2'-nitrobiphenyl

There total 19 articles about 4-Acetyl-2'-nitrobiphenyl 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: 91.0%

4-Iodoacetophenone (13329-40-3) + ortho-nitrobenzoic acid (552-16-9,104810-18-6) → 4-acetyl-2'-nitrobiphenyl (5730-96-1)

Guidance literature:

With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N,N-dimethyl-aniline; silver carbonate; palladium dichloride; at 150 ℃; for 2h;

DOI:10.1016/j.tet.2009.04.047

Reference yield: 88.0%

para-bromoacetophenone (99-90-1) + potassium o-nitrobenzoate (15163-59-4) → 4-acetyl-2'-nitrobiphenyl (5730-96-1)

Guidance literature:

With palladium(II) acetylacetonate; N,N,N,N,-tetramethylethylenediamine; copper(I) bromide; In 1-methyl-pyrrolidin-2-one; at 170 ℃; for 3h; chemoselective reaction; Inert atmosphere;

DOI:10.1002/adsc.201201018

Reference yield: 86.0%

2-nitrophenyl bromide (577-19-5) + 4-acetylphenylboronic acid (149104-90-5) → 4-acetyl-2'-nitrobiphenyl (5730-96-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In 1,4-dioxane; water; at 100 ℃; for 1h; Inert atmosphere;

upstream raw materials:

2-nitrobiphenyl

acetyl chloride

biphenyl-4-acetaldehyde

2-nitrophenylboronic acid

Downstream raw materials:

2-acetylcarbazole

methyl 2'-amino-[1,1'-biphenyl]-4-carboxylate

methyl 2′-amino-[1,1′-biphenyl]-4-carboxylate

Refernces

• 1、 -. "Method for preparing 24'-acetyl 4-nitrobiphenyl and 14' -acetyl 2-nitrobiphenyl through nitrification of 4-acetylbiphenyl". Paragraph 0033; 0034. . Retrieved 2017/08/30.
• 2、 Yuan, Ming,Chen, Li,Wang, Junwei,Chen, Shenjie,Wang, Kongchao,Xue, Yongbo,Yao, Guangmin,Luo, Zengwei,Zhang, Yonghui. "Transition-metal-free synthesis of phenanthridinones from biaryl-2-oxamic acid under radical conditions". supporting information. p. 346 - 349. Retrieved 2015/02/19.