9-ethyl-3-[(Z)-2-nitroethenyl]carbazole

Base Information

• Chemical Name: 9-ethyl-3-[(Z)-2-nitroethenyl]carbazole
• CAS No.: 57412-02-9
• Molecular Formula: C₁₆H₁₄N₂O₂
• Molecular Weight: 266.299
• NSC Number: 177958
• Mol file: 57412-02-9.mol

Synonyms:NSC177958;NSC-177958;57412-02-9

Chemical Property of 9-ethyl-3-[(Z)-2-nitroethenyl]carbazole

Chemical Property:

• Vapor Pressure: 7.33E-07mmHg at 25°C
• Boiling Point: 407.8°Cat760mmHg
• Flash Point: 200.4°C
• Density: 1.21g/cm³
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 266.105527694
• Heavy Atom Count: 20
• Complexity: 390

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C2=C(C=C(C=C2)C=C[N+](=O)[O-])C3=CC=CC=C31
• Isomeric SMILES: CCN1C2=C(C=C(C=C2)/C=C\[N+](=O)[O-])C3=CC=CC=C31

Technology Process of 9-ethyl-3-[(Z)-2-nitroethenyl]carbazole

There total 3 articles about 9-ethyl-3-[(Z)-2-nitroethenyl]carbazole 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%

nitromethane (75-52-5) + N-ethyl-3-carbazolealdehyde (7570-45-8) → 9-Ethyl-3-((E)-2-nitro-vinyl)-9H-carbazole (57412-02-9)

Guidance literature:

With ammonium acetate; acetic acid; for 3h; Reflux;

DOI:10.1039/c5ra25204k

Reference yield:

9H-carbazole (86-74-8,105184-46-1,97960-57-1) → 9-Ethyl-3-((E)-2-nitro-vinyl)-9H-carbazole (57412-02-9)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / N,N-dimethyl-formamide / 18 h / 20 °C

2: titanium tetrachloride / dichloromethane / 4 h / -78 °C

3: ammonium acetate; acetic acid / 2 h / 80 °C

With ammonium acetate; titanium tetrachloride; sodium hydride; acetic acid; In dichloromethane; N,N-dimethyl-formamide; 2: |Rieche Formylation / 3: |Henry Nitro Aldol Condensation;

DOI:10.1071/CH16169

Reference yield:

N-ethylcarbazole (86-28-2) → 9-Ethyl-3-((E)-2-nitro-vinyl)-9H-carbazole (57412-02-9)

Guidance literature:

Multi-step reaction with 2 steps

1: titanium tetrachloride / dichloromethane / 4 h / -78 °C

2: ammonium acetate; acetic acid / 2 h / 80 °C

With ammonium acetate; titanium tetrachloride; acetic acid; In dichloromethane; 1: |Rieche Formylation / 2: |Henry Nitro Aldol Condensation;

DOI:10.1071/CH16169

upstream raw materials:

nitromethane

N-ethyl-3-carbazolealdehyde

9H-carbazole

N-ethylcarbazole

Refernces

• 1、 Avula, Vijay Kumar Reddy,Vallela, Swetha,Anireddy, Jaya Shree,Chamarthi, Naga Raju. "p-TsOH-mediated, Versatile, and Efficient Approach for the Synthesis of Triazolyl-Carbazoles from Nitrovinylcarbazoles and Azide via 1, 3-Dipolar Cycloaddition". . p. 1361 - 1368. Retrieved 2017/03/27.
• 2、 Berghot, Moged Ahmed,Badawy, Doria Saleh,Moawad, Evelin Boshra. "FACILE SYNTHESIS OF NOVEL CARBAZOLES THROUGH HETEROCYCLIZATION REACTIONS AND THEIR ANTIMICROBIAL ACTIVITY". . p. 377 - 386. Retrieved 2007/10/03.