1-Nitro-4-phenylbutadiene

Base Information

• Chemical Name: 1-Nitro-4-phenylbutadiene
• CAS No.: 4701-10-4
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.187
• Nikkaji Number: J2.508.802F,J865.635E,J2.807.049G
• Mol file: 4701-10-4.mol

Synonyms:1-nitro-4-phenyl-1,3-butadiene;1-nitro-4-phenylbutadiene;1-nitro-4-phenylbutadiene, (E,E)-isomer

Chemical Property of 1-Nitro-4-phenylbutadiene

Chemical Property:

• Vapor Pressure: 0.000791mmHg at 25°C
• Melting Point: 46 - 48 °C
• Boiling Point: 315.8°Cat760mmHg
• Flash Point: 150.6°C
• PSA: 45.82000
• Density: 1.142g/cm³
• LogP: 3.01340
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 210

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 1-Nitro-4-phenylbutadiene

There total 15 articles about 1-Nitro-4-phenylbutadiene 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: 93.0%

2-hydroxy-1-nitro-4-phenyl-but-3-ene → ((1E,3E)-4-nitrobuta-1,3-dien-1-yl)benzene (4701-10-4,28925-75-9)

Guidance literature:

2-hydroxy-1-nitro-4-phenyl-but-3-ene; With potassium carbonate; In water; for 0.25h; Green chemistry;

With hydrogenchloride; In water; pH=6; Green chemistry;

DOI:10.1080/00397911.2014.926373

Reference yield: 90.0%

nitromethane (75-52-5) + 3-phenyl-propenal (104-55-2) → 1-nitro-4-phenylbutadiene (28925-75-9,4701-10-4)

Guidance literature:

With ammonium acetate; at 60 ℃; for 0.75h; Ultrasound irradiation;

DOI:10.1016/j.tetlet.2011.03.037

Reference yield: 77.1%

(E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene (108030-46-2) + phenylmagnesium bromide (100-58-3) → ((1E,3E)-4-nitrobuta-1,3-dien-1-yl)benzene (4701-10-4,28925-75-9)

Guidance literature:

In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.3987/COM-97-7787

upstream raw materials:

nitromethane

3-phenyl-propenal

1,1,1-trideuteromethanol

buta-1,3-dien-1-ylbenzene

Downstream raw materials:

(E)-2-(cyclohex-1-enyl)-4-nitro-3-(2-phenylethenyl)pyrrole

(1R,2R,3R,4S)-benzyl 4-((ethoxycarbonyl)methyl)-1-acetyl-3-nitro-2-styrylcyclopentanecarboxylate

ethyl (1R,2R,3S,4R)-1-acetyl-4-hydroxy-4-methyl-3-nitro-2-((E)-styryl)cyclohexanecarboxylate

2-((R,E)-1-nitro-4-phenylbut-3-en-2-yl)-1,3-diphenylpropane-1,3-dione

Refernces

• 1、 Yu, Bangkui,Gao, Bao,Zhang, Xuexia,Zhang, Haocheng,Huang, Hanmin. "Palladium-Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation". supporting information. p. 566 - 570. Retrieved 2021/02/01.
• 2、 Li, Jian,Hu, Qi-Long,Chen, Xue-Ping,Hou, Ke-Qiang,Chan, Albert S.C.,Xiong, Xiao-Feng. "Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin". supporting information. p. 697 - 700. Retrieved 2019/09/30.