3-Vinylaniline

Base Information

• Chemical Name: 3-Vinylaniline
• CAS No.: 15411-43-5
• Molecular Formula: C8H9N
• Molecular Weight: 119.166
• Hs Code.: 2921420090
• European Community (EC) Number: 626-660-5
• DSSTox Substance ID: DTXSID40401335
• Nikkaji Number: J693.746B
• Wikidata: Q82204417
• Mol file: 15411-43-5.mol

Synonyms:3-Vinylaniline;15411-43-5;3-ethenylaniline;3-Aminostyrene;MFCD00017105;Benzenamine, 3-ethenyl-;m-AMINOSTYRENE;3-vinyl-aniline;3-Amino styrene;meta amino vinyl benzene;SCHEMBL250060;DTXSID40401335;AMY31946;AKOS006340200;CS-W011211;AS-56530;SY014136;m-Vinylaniline (contains KOH as inhibitor);FT-0692280;3-Vinylaniline, contains KOH as inhibitor, 97%;A883752

Chemical Property of 3-Vinylaniline

Chemical Property:

• Refractive Index: n20/D 1.611(lit.)
• Boiling Point: 240.4 °C at 760 mmHg
• PKA: 4.39±0.10(Predicted)
• Flash Point: 109.7 °C
• PSA: 26.02000
• Density: 1.012 g/cm³
• LogP: 2.49300
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 119.073499291
• Heavy Atom Count: 9
• Complexity: 98.7

Purity/Quality:

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

m-Vinylaniline(containsKOHasinhibitor) ^*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

Useful:

• Canonical SMILES: C=CC1=CC(=CC=C1)N
• Uses: The formation of m-Vinylaniline from the reduction of m-Nitrostyrene containing an easily reducible vinyl-group using hydrazine hydrate as the reducing agent.

Technology Process of 3-Vinylaniline

There total 34 articles about 3-Vinylaniline 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: 90.0%

3-acetylenephenylamine (54060-30-9) → 3-vinylaniline (15411-43-5)

Guidance literature:

3-acetylenephenylamine; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In 1,4-dioxane; at 20 ℃; for 0.25h; Inert atmosphere;

With formic acid; In 1,4-dioxane; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ja2069246

Reference yield: 84.0%

1-nitro-3-vinyl-benzene (586-39-0,51209-60-0) → 3-vinylaniline (15411-43-5) + m-ethylaniline (587-02-0)

Guidance literature:

With ammonia borane; gold on titanium oxide; In ethanol; at 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1002/adsc.201200983

Reference yield: 82.0%

1-nitro-3-vinyl-benzene (586-39-0,51209-60-0) → 3-vinylaniline (15411-43-5) + N,N'-bis-(3-vinylphenyl)hydrazine (329763-36-2)

Guidance literature:

With samarium; 1,1’-di-n-octyl-4,4’-bipyridinium dibromide; In methanol; at 20 ℃; for 2h;

DOI:10.1021/jo005666q

upstream raw materials:

1-nitro-3-vinyl-benzene

3-(1-hydroxyethyl)aniline

hydrogenchloride

zinc

Downstream raw materials:

N-(3-vinylphenyl)acetamide

m-ethylaniline

8-[2-(3-aminophenyl)ethyl]-2-chloro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

(S)-N-[(tert-butyloxy)carbonyl]-[3-N,N'-bis(tert-butyloxy)carbonyl(guanyl)aminophenyl]glycine

Refernces

• 1、 Carrillo, Adela I.,Stamplecoskie, Kevin G.,Marin, M. Luisa,Scaiano, Juan C.. "'From the mole to the molecule': Ruthenium catalyzed nitroarene reduction studied with 'bench', high-throughput and single molecule fluorescence techniques". . p. 1989 - 1996. Retrieved 2014.
• 2、 Tan, Yuan,Liu, Xiao Yan,Li, Lin,Kang, Leilei,Wang, Aiqin,Zhang, Tao. "Effects of divalent metal ions of hydrotalcites on catalytic behavior of supported gold nanocatalysts for chemoselective hydrogenation of 3-nitrostyrene". . p. 174 - 182. Retrieved 2018.
• 3、 Wei, Haisheng,Wei, Xing,Yang, Xiaofeng,Yin, Guangzhao,Wang, Aiqin,Liu, Xiaoyan,Huang, Yanqiang,Zhang, Tao. "Supported Au-Ni nano-alloy catalysts for the chemoselective hydrogenation of nitroarenes". . p. 160 - 167. Retrieved 2015.
• 4、 Nuzhdin,Reshetnikov,Bukhtiyarova,Moroz,Gerasimov, E. Yu.,Pyrjaev,Bukhtiyarov. "Study of Catalyst Deactivation in Liquid-Phase Hydrogenation of 3-Nitrostyrene Over Au/Al2O3 Catalyst in Flow Reactor". . p. 572 - 580. Retrieved 2017.
• 5、 Lu, Ting,Lin, Jian,Liu, Xin,Wang, Xiaodong,Zhang, Tao. "Structure Evolution and Hydrogenation Performance of IrFe Bimetallic Nanomaterials". . p. 2771 - 2779. Retrieved 2016.
• 6、 Boronat, Merce,Concepcion, Patricia,Corma, Avelino,Gonzalez, Silvia,Illas, Francesc,Serna, Pedro. "A molecular mechanism for the chemoselective hydrogenation of substituted nitroaromatics with nanoparticles of gold on TiO2 catalysts: A cooperative effect between gold and the support". . p. 16230 - 16237. Retrieved 2007.
• 7、 Wu, Qifan,Zhang, Bin,Zhang, Chao,Meng, Xiangchun,Su, Xinluona,Jiang, Shan,Shi, Ruhui,Li, Yan,Lin, Weiwei,Arai, Masahiko,Cheng, Haiyang,Zhao, Fengyu. "Significance of surface oxygen-containing groups and heteroatom P species in switching the selectivity of Pt/C catalyst in hydrogenation of 3-nitrostyrene". . p. 297 - 307. Retrieved 2018.
• 8、 Chen, Jian,Yao, Yi,Zhao, Jiao,Zhao, Yaopeng,Zheng, Yuanyuan,Li, Mingrun,Yang, Qihua. "A highly active non-precious metal catalyst based on Fe-N-C@CNTs for nitroarene reduction". . p. 96203 - 96209. Retrieved 2016.
• 9、 Mikami, Yusuke,Noujima, Akifumi,Mitsudome, Takato,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi. "Highly chemoselective reduction of nitroaromatic compounds using a hydrotalcite-supported silver-nanoparticle catalyst under a CO atmosphere". . p. 223 - 225. Retrieved 2010.
• 10、 Xu, Kunling,Zhang, Yuan,Chen, Xiaorong,Huang, Lei,Zhang, Rui,Huang, Jun. "Convenient and selective hydrogenation of nitro aromatics with a platinum nanocatalyst under ambient pressure". . p. 1260 - 1264. Retrieved 2011.