4-Nitrostilbene

Base Information

• Chemical Name: 4-Nitrostilbene
• CAS No.: 1694-20-8
• Molecular Formula: C14H11 N O2
• Molecular Weight: 225.247
• Hs Code.: 2904209090
• European Community (EC) Number: 223-653-5
• NSC Number: 141579,66821,53390
• UNII: 3W1GSV923H
• DSSTox Substance ID: DTXSID801314725
• Nikkaji Number: J61.351G,J854.751C
• Wikidata: Q27105156
• Metabolomics Workbench ID: 27961
• ChEMBL ID: CHEMBL355211
• Mol file: 1694-20-8.mol

Synonyms:4-Nitrostilbene;(E)-4-Nitrostilbene;trans-p-Nitrostilbene;4003-94-5;1694-20-8;trans-4-Nitrostilbene;p-Nitrostilbene;4-Nitrostilben;Stilbene, 4-nitro-;1-Nitro-4-[(E)-2-phenylethenyl]benzene;1-NITRO-4-((E)-STYRYL)-BENZENE;(E)-1-Nitro-4-styrylbenzene;Stilbene, 4-nitro-, (E)-;Benzene, 1-nitro-4-(2-phenylethenyl)-, (E)-;Benzene, 1-nitro-4-(2-phenylethenyl)-;(E)-1-Nitro-4-(2-phenylethenyl)benzene;4-Nitrostilben [German];NSC 66821;1-Nitro-4-styryl-benzene;BRN 1311157;beta-(4-Nitrophenyl)styrene;UNII-3W1GSV923H;1-nitro-4-[(E)-2-phenylvinyl]benzene;3W1GSV923H;CCRIS 1664;CCRIS 8463;CHEBI:377106;EINECS 223-653-5;NSC 141579;NSC-141579;MFCD00053614;4-Nitro-trans-stilbene;1-nitro-4-styrylbenzene;1-nitro-4-(2-phenylethenyl)benzene;Stilbene, 4-nitro-, (Z)-;cis-p-Nitrostilbene;4-Nitrostilbene, trans;Benzene, 1-nitro-4-(2-phenylethenyl)-, (Z)-;trans-4-Mononitrostilbene;NITROSTILBENE, 4-;WLN: WNR D1U1R;CHEMBL355211;SCHEMBL1405432;DTXSID801314725;NSC53390;NSC66821;LMPK13090020;NSC-53390;NSC-66821;NSC141579;STK523960;AKOS002792504;AKOS015965834;.BETA.-(4-NITROPHENYL)STYRENE;NCGC00342619-01;BS-23275;1-PHENYL-2-(4-NITROPHENYL)ETHENE;1-nitro-4-[(1E)-2-phenylethenyl]benzene;LS-146869;1-Nitro-4-[(E)-2-phenylethenyl]benzene #;CS-0210321;N0549;1-nitro-4-[(E)-2-phenyl-1-ethenyl]benzene;benzene, 1-nitro-4-[(E)-2-phenylethenyl]-;AB01333700-02;Benzene, 1-nitro-4-(2-phenylethenyl)- (9CI);A873499;Q27105156;Benzene, 1-nitro-4-(2-phenylethenyl)-, (E)- (9CI)

Chemical Property of 4-Nitrostilbene

Chemical Property:

• Vapor Pressure: 0.000145mmHg at 25°C
• Melting Point: 155.0 to 159.0 °C
• Refractive Index: 1.5780 (estimate)
• Boiling Point: 342.8°Cat760mmHg
• Flash Point: 153.5°C
• PSA: 45.82000
• Density: 1.22g/cm³
• LogP: 4.28840
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 225.078978594
• Heavy Atom Count: 17
• Complexity: 268

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Nitrostilbene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC2=CC=C(C=C2)[N+](=O)[O-]
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/C2=CC=C(C=C2)[N+](=O)[O-]

Technology Process of 4-Nitrostilbene

There total 292 articles about 4-Nitrostilbene 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%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + p-nitrobenzene iodide (636-98-6) → 4-nitrostilbene (1694-20-8,4003-94-5,6624-53-9,101977-34-8)

Guidance literature:

With potassium carbonate; In ethanol; water; at 90 ℃; for 10h; Green chemistry;

DOI:10.1016/j.apcata.2014.02.002

Reference yield: 98.0%

4-nitrostyrene (100-13-0) + iodobenzene (591-50-4) → 4-nitrostilbene (1694-20-8,4003-94-5,6624-53-9,101977-34-8)

Guidance literature:

With triethylamine; In water; acetonitrile; at 60 ℃; for 2h;

DOI:10.1080/00958972.2019.1687890

Reference yield: 97.8%

p-nitrostilbene dibromide (26624-20-4) → 4-nitrostilbene (1694-20-8,4003-94-5,6624-53-9,101977-34-8)

Guidance literature:

With dibutyl telluride; triethylamine; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1080/00304949609355916

upstream raw materials:

piperidine

1-methyl-4-nitrobenzene

benzaldehyde

(E)-1,2-diphenyl-ethene

Downstream raw materials:

4-nitrostilbene

4-aminodibenzyl

p-amino-trans-stilbene

N-nitroso-N-trans-stilben-4-yl-hydroxylamine

Refernces

• 1、 Yorke, Jake,Wan, Li,Xia, Aibing,Zheng, Wenjun. "Catalytic applications of 1,2,4-diazaphospholide-based ruthenium complexes in the Heck reaction". . p. 8843 - 8845. Retrieved 2007.
• 2、 Todres, Z. V.,Kuryaeva, T. T.,Ryzhova, G. L.,Kursanov, D. N.. "cis-trans ISOMERIZATION OF NITROSTILBENES IN THE PRESENCE OF AROMATIC AMINES". . p. 1145 - 1148. Retrieved 1980.
• 3、 Beller, Matthias,Krauter, Juergen Gregor Elmar,Zapf, Alexander. "Carbohydrate-Substituted Triarylphosphanes - A New Class of Ligands for Two-Phase Catalysis". . p. 772 - 774. Retrieved 1997.
• 4、 Todres et al.. "". . . Retrieved 1974.
• 5、 Ludolph, Bj?rn,Klein, Markus,Erdinger, Lothar,Boche, Gernot. "The effects of 4′-alkyl substituents on the mutagenic activity of 4-amino- and 4-nitrostilbenes in Salmonella typhimurium". . p. 195 - 209. Retrieved 2001.
• 6、 Mehnert, Christian P.,Weaver, David W.,Ying, Jackie Y.. "Heterogeneous heck catalysis with palladium-grafted molecular sieves". . p. 12289 - 12296. Retrieved 1998.
• 7、 Min, Qingwang,Miao, Penghua,Chu, Deyu,Liu, Jinghan,Qi, Meijuan,Kazemnejadi, Milad. "Introduction of a Recyclable Basic Ionic Solvent with Bis-(NHC) Ligand Property and The Possibility of Immobilization on Magnetite for Ligand- and Base-Free Pd-Catalyzed Heck, Suzuki and Sonogashira Cross-Coupling Reactions in Water". . p. 3030 - 3047. Retrieved 2021/02/16.
• 8、 Rahimi, Leila,Mansoori, Yagoub,Nuri, Ayat,Koohi-Zargar, Behzad,Esquivel, Dolores. "A new Pd(II)-supported catalyst on magnetic SBA-15 for C-C bond formation via the Heck and Hiyama cross-coupling reactions". . . Retrieved 2020/12/01.