2-Vinylaniline

Base Information

• Chemical Name: 2-Vinylaniline
• CAS No.: 3867-18-3
• Molecular Formula: C8H9N
• Molecular Weight: 119.166
• Hs Code.: 2921420090
• DSSTox Substance ID: DTXSID40438449
• Nikkaji Number: J28.426B
• Wikidata: Q82254201
• Mol file: 3867-18-3.mol

Synonyms:2-vinylaniline;3867-18-3;2-ethenylaniline;2-aminostyrene;2-Vinylbenzenamine;MFCD11878483;o-aminostyrene;2-vinyl-aniline;(2-vinyl-phenyl)-amine;SCHEMBL30273;DTXSID40438449;KURPPWHPIYBYBS-UHFFFAOYSA-N;BCP24389;AKOS006340622;CS-W006235;DS-3464;SB75473;SY110137;EN300-332078;A873797;J-510360

Chemical Property of 2-Vinylaniline

Chemical Property:

• Refractive Index: 1.6124
• Boiling Point: 219.505 °C at 760 mmHg
• PKA: 3.86±0.10(Predicted)
• Flash Point: 93.84 °C
• PSA: 26.02000
• Density: 1.013 g/cm³
• LogP: 2.49300
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2
• 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:

97% ^*data from raw suppliers

2-Vinylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1=CC=CC=C1N
• General Description: 2-AMINOSTYRENE (also known as 2-vinylaniline) is a key intermediate in the synthesis of 2-chloroquinolines, where it reacts with diphosgene in acetonitrile to form phenyl isocyanate, followed by cyclization and chlorination. 2-AMINOSTYRENE plays a crucial role in facilitating a safer and more efficient route to 2-chloroquinolines by avoiding hazardous reagents like phosphorus oxychloride. Its reactivity in nitrile solvents underscores its utility in heterocyclic synthesis.

Technology Process of 2-Vinylaniline

There total 46 articles about 2-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: 97.0%

2-nitrostyrene (579-71-5) → 2-vinylaniline (3867-18-3)

Guidance literature:

With hydrazine hydrate; In ethanol; at 20 ℃; for 4h; chemoselective reaction;

DOI:10.1021/acscatal.5b00830

Reference yield: 88.0%

2-aminophenethyl alcohol (5339-85-5) → 2-vinylaniline (3867-18-3)

Guidance literature:

With potassium hydroxide;

DOI:10.1002/cjoc.201800258

Reference yield: 87.0%

2-chlorostyrene (2039-87-4,107830-52-4,26125-41-7) → 2-vinylaniline (3867-18-3)

Guidance literature:

With C₃₉H₄₅FeNNiP₂; ammonia; sodium t-butanolate; In 1,4-dioxane; at 100 ℃; for 3h; Reagent/catalyst; Solvent; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201500404

upstream raw materials:

2-nitrostyrene

2-aminophenethyl alcohol

Isopropylbenzene

2-ethylthio-N-allylaniline

Downstream raw materials:

N,N'-bis-(2-vinyl-phenyl)-adipamide

chloro-acetic acid-(2-vinyl-anilide)

N-(2-vinylphenyl)acetamide

N-p-toluenesulfonyl-2-vinylaniline

Refernces

Novel synthesis of 2-chloroquinolines from 2-vinylanilines in nitrile solvent

10.1021/jo016196i

The study presents a novel method for synthesizing 2-chloroquinolines from 2-vinylanilines using diphosgene in acetonitrile as the solvent. The researchers detail a three-step reaction mechanism involving the generation of phenylisocyanate, quinoline ring formation, and chlorination at the C2 position of the quinoline. The purpose of the chemicals used in the study was to facilitate these steps, with diphosgene reacting with 2-vinylanilines to produce phenyl isocyanate, which then reacts with the acetonitrile to form the quinoline ring. The final step involves the chlorination of the C2 position. This new method eliminates the need for the hazardous use of excess phosphorus oxychloride, which was previously required in the synthesis of 2-chloroquinolines from 2(1H)-quinolinones. The study also discusses the role of acetonitrile as a reactive solvent in the process and provides evidence that the third step, chlorination, is likely the rate-determining step in the reaction.