trans-beta-Nitrostyrene

Base Information

• Chemical Name: trans-beta-Nitrostyrene
• CAS No.: 102-96-5
• Molecular Formula: C8H7 N O2
• Molecular Weight: 149.149
• 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: 102-96-5.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
• Vapor Pressure: 0.0255mmHg at 25°C
• Melting Point: 55-58 °C(lit.)
• Refractive Index: 1.5320 (estimate)
• Boiling Point: 250-260 °C(lit.)
• Flash Point: 117.5°C
• PSA: 45.82000
• Density: 1.177g/cm³
• LogP: 2.45720
• Storage Temp.: 2-8°C
• 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:

(2-Nitrovinyl)benzene 95+% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

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-]

Technology Process of trans-beta-Nitrostyrene

There total 88 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: 97.5%

nitromethane (75-52-5) + benzaldehyde dimethyl acetal (1125-88-8) → (2-nitroethenyl)benzene (102-96-5) + benzaldehyde (100-52-7)

Guidance literature:

With benzenesulfonic acid and amine group containing periodic mesoporous organosilica; at 90 ℃; for 20h;

DOI:10.1002/anie.200903985

Reference yield: 80.0%

nitromethane (75-52-5) + benzaldehyde (100-52-7) → (2-nitroethenyl)benzene (102-96-5) + (1,3-dinitropropan-2-yl)benzene (117538-84-8)

Guidance literature:

With hexan-1-amine; silica gel; In toluene; at 90 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2017.12.050

Reference yield: 38.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → (2-nitroethenyl)benzene (102-96-5) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With tert.-butylnitrite; oxygen; In water; dimethyl sulfoxide; at 50 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2018.10.037

upstream raw materials:

styrene

(E)-3-phenylacrylic acid

2-nitro-1-phenylethan-1-ol

nitromethane

Downstream raw materials:

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

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

5-benzyloxy-3-(2-nitro-1-phenyl-ethyl)-indole

palmitic acid-[N'-(2-nitro-1-phenyl-ethyl)-hydrazide]

Refernces

• 1、 Nakamura, Shohei,Takagaki, Atsushi,Watanabe, Motonori,Yamada, Kanta,Yoshida, Masaaki,Ishihara, Tatsumi. "Porous Boron Nitride as a Weak Solid Base Catalyst". . p. 6033 - 6039. Retrieved 2020.
• 2、 Worrall. "-". . p. 1556,1558. Retrieved 1934.
• 3、 Ahadi,Naghdiani,Balalaie,Rominger. "Diastereoselective synthesis of polysubstituted cyclopentanols and cyclopentenes containing stereogenic centers via domino Michael/cyclization reaction". . p. 6860 - 6866. Retrieved 2015.
• 4、 Zhu, Feng-Xia,Zhao, Pu-Su,Sun, Xiao-Jun,An, Li-Tao,Deng, Yong,Wu, Jia-Min. "Direct synthesis and application of bridged diamino-functionalized periodic mesoporous organosilicas with high nitrogen contents". . p. 70 - 75. Retrieved 2017.
• 5、 Lang, Wanzhong,Su, Bo,Guo, Yajun,Chu, Lianfeng. "Preparation and synergetic catalytic effects of amino-functionalized MCM-41 catalysts". . p. 1167 - 1174. Retrieved 2012.
• 6、 Suzuki, Hitomi,Mori, Tadashi. "Side-Chain Nitration of Styrene and Para-Substituted Derivatives with a Combination of Nitrogen Dioxide and Ozone". . p. 6498 - 6502. Retrieved 1997.
• 7、 Gavrilin et al.. "-". . . Retrieved 1973.
• 8、 Ertugrul, Berrak,Kilic, Haydar,Lafzi, Farrokh,Saracoglu, Nurullah. "Access to C5-Alkylated Indolines/Indoles via Michael-Type Friedel-Crafts Alkylation Using Aryl-Nitroolefins". . p. 9018 - 9038. Retrieved 2018.
• 9、 Balachandra, Biguvu,Shanmugam, Sivakumar,Muneeswaran, Thillaichidambaram,Ramakritinan, Muthiah. "Iodine catalyzed one-pot synthesis of highly substituted N-methyl pyrroles via [3 + 2] annulation and their in vitro evaluation as antibacterial agents". . p. 64781 - 64789. Retrieved 2015.
• 10、 Yan, Qiaozhi,Liu, Man,Kong, Duanyang,Zi, Guofu,Hou, Guohua. "Highly efficient iridium-catalyzed asymmetric hydrogenation of β-acylamino nitroolefins". . p. 12870 - 12872. Retrieved 2014.