trans-beta-Nitrostyrene

Base Information

• Chemical Name: trans-beta-Nitrostyrene
• CAS No.: 5153-67-3
• Molecular Formula: C8H7NO2
• Molecular Weight: 149.149
• Hs Code.: 29042090
• European Community (EC) Number: 203-066-0,629-597-1
• NSC Number: 9809
• UNII: 5287E3OUAV
• DSSTox Substance ID: DTXSID6033247
• Nikkaji Number: J61.359B,J9.722E
• Wikipedia: Beta-Nitrostyrene
• Wikidata: Q54551957
• ChEMBL ID: CHEMBL230156
• Mol file: 5153-67-3.mol

Synonyms:1-nitro-2-phenylethylene;2-nitro-1-phenylethylene;beta-nitrostyrene;beta-nitrostyrene, (E)-isomer;nitrostyrol

Chemical Property of trans-beta-Nitrostyrene

Chemical Property:

• Appearance/Colour: yellow crystals.
• Melting Point: 55-58 °C
• Refractive Index: 1.5320 (estimate)
• Boiling Point: 255.8 °C at 760 mmHg
• Flash Point: 117.5 °C
• PSA: 45.82000
• Density: 1.177 g/cm³
• LogP: 2.45720
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol
• Water Solubility.: Insoluble in water.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 149.047678466
• Heavy Atom Count: 11
• Complexity: 154

Purity/Quality:

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

trans-β-Nitrostyrene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC=C(C=C1)C=C[N+](=O)[O-]
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/[N+](=O)[O-]
• Uses: trans-β-Nitrostyrene, and its derivatives such as 3,4-methylenedioxy-β-nitrostyrene (MNS) and 4-O-benzoyl-3-methoxy-β-nitrostyrene (BMNS), has shown to exhibit potent anti-platelet activities and cytotoxicity.

Technology Process of trans-beta-Nitrostyrene

There total 70 articles about trans-beta-Nitrostyrene 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: 99.0%

nitromethane (75-52-5) + benzaldehyde (100-52-7) → nitrostyrene (5153-67-3)

Guidance literature:

With sulfonic acid amine MCM-41 mesoporous silica nanoparticles; at 90 ℃; for 20h; Temperature;

DOI:10.1002/chem.201200499

Reference yield: 96.0%

2-nitro-1-phenylethan-1-ol (141377-54-0,145920-96-3,149495-00-1,15990-45-1) → nitrostyrene (5153-67-3)

Guidance literature:

2-nitro-1-phenylethan-1-ol; 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: 95.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → nitrostyrene (5153-67-3)

Guidance literature:

With silver(I) nitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In 1,2-dichloro-ethane; at 70 ℃; for 12h; Reagent/catalyst; Solvent; Concentration; stereoselective reaction; Kinetics; Molecular sieve; Inert atmosphere;

DOI:10.1021/ja311942e

upstream raw materials:

styrene

ethylbenzene

(1,2-dibromo-2-nitroethyl)benzene

nitromethane

Downstream raw materials:

2-methyl-3-(2-nitro-1-phenylethyl)-1H-indole

3,5-Diphenyl-4-nitroisoxazoline

1,2-dimethyl-3-(2-nitro-1-phenyl-ethyl)-indole

(2-nitro-1-phenyl-ethyl)-p-tolyl sulfone

Refernces

• 1、 Mei,Tao,Long,Ming,Liang,Rong. "Synthesis and catalytic activity of novel Ni-N complexes1". . p. 567 - 572. Retrieved 2012.
• 2、 Shiju, N. Raveendran,Alberts, Albert H.,Khalid, Syed,Brown, David R.,Rothenberg, Gadi. "Mesoporous silica with site-isolated amine and phosphotungstic acid groups: A solid catalyst with tunable antagonistic functions for one-pot tandem reactions". . p. 9615 - 9619. Retrieved 2011.
• 3、 Min, Sun-Joon,Park, Sangwoon,Yoon, Seungri. "Metal-free Synthesis of β-Nitrostyrenes via DDQ-Catalyzed Nitration". . p. 525 - 528. Retrieved 2021/02/22.
• 4、 Wu, Jianbing,Yin, Wei,Huang, Zhangjian,Zhang, Yinqiu,Jia, Jian,Cheng, Huimin,Kang, Fenghua,Huang, Kai,Sun, Tao,Tian, Jide,Xu, Xiaojun,Zhang, Yihua. "Design, Synthesis, and Biological Evaluation of Organic Nitrite (NO 2-) Donors as Potential Anticerebral Ischemia Agents". . p. 10919 - 10933. Retrieved 2021/08/16.