9-Allyl-9H-carbazole

Base Information

• Chemical Name: 9-Allyl-9H-carbazole
• CAS No.: 3998-04-7
• Molecular Formula: C15H13N
• Molecular Weight: 207.275
• European Community (EC) Number: 660-534-0
• DSSTox Substance ID: DTXSID40389048
• Nikkaji Number: J570.224K
• Wikidata: Q82184425
• ChEMBL ID: CHEMBL4531380
• Mol file: 3998-04-7.mol

Synonyms:9-Allyl-9H-carbazole;3998-04-7;9-Allylcarbazole;9-prop-2-enylcarbazole;N-allylcarbazole;9-allyl carbazole;9-(prop-2-en-1-yl)-9H-carbazole;SCHEMBL146503;CHEMBL4531380;DTXSID40389048;GHBQLFWTMLRYKN-UHFFFAOYSA-N;HMS1671O15;MFCD00093414;STK726944;AKOS000629510;DS-10918;CS-0162716;C75021;A912189;SR-01000395854;SR-01000395854-1;BRD-K06217091-001-01-7

Chemical Property of 9-Allyl-9H-carbazole

Chemical Property:

• Melting Point: 56 °C
• Boiling Point: 359.9±25.0 °C(Predicted)
• PSA: 4.93000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 3.98050
• Storage Temp.: 2-8°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 207.104799419
• Heavy Atom Count: 16
• Complexity: 238

Purity/Quality:

98.5% ^*data from raw suppliers

9-Allyl-9H-carbazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCN1C2=CC=CC=C2C3=CC=CC=C31
• General Description: 9-ALLYLCARBAZOLE (also known as 9-allyl-carbazole, 9-(2-propenyl)carbazole, or N-allyl carbazole) is a nitrogen-containing olefin that reacts with cationic (R-diimine)Pd-Me species to form a reactive three-membered chelate complex, enabling its potential use in catalytic copolymerization with ethylene to produce branched polyethylene with carbazole functionalities. This contrasts with other nitrogen-containing olefins, such as allyl dimethyl amine, which forms an inert five-membered chelate complex.

Technology Process of 9-Allyl-9H-carbazole

There total 2 articles about 9-Allyl-9H-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: 55.0%

9H-carbazole (86-74-8,105184-46-1,97960-57-1) + 1,3-dibromo-propane (109-64-8) → 9-allyl-9H-carbazole (3998-04-7) + 9-(3-bromopropyl)-9H-carbazole (84359-61-5)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In water; benzene;

DOI:10.1016/S0040-4020(02)00331-9

Reference yield:

ethylene dibromide (106-93-4) + 9-(3-bromopropyl)-9H-carbazole (84359-61-5) → 9-allyl-9H-carbazole (3998-04-7)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; water;

DOI:10.1016/S0040-4020(02)00331-9

Reference yield: 93.0%

9-allyl-9H-carbazole (3998-04-7) + triphenylphosphonium tetrafluoroborate → (x)BF4*C33H29NP(1+)

Guidance literature:

With triphenylphosphine; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere; UV-irradiation;

DOI:10.1021/ol202790n

upstream raw materials:

9H-carbazole

1,3-dibromo-propane

ethylene dibromide

9-(3-bromopropyl)-9H-carbazole

Downstream raw materials:

9H-carbazole

9-(oxiran-2-ylmethyl)-9H-carbazole

[(2,6-(i-Pr)2C₆H₃N=C(Me)C(Me)=N-2,6-(i-Pr)2C₆H₃)Pd(Me₂CHCHN(C₆H₄)2)][B(3,5-(CF₃)2C₆H₃)4]

Refernces

Reactions of cationic palladium α-diimine complexes with nitrogen-containing olefins: Branched polyethylene with carbazole functionalities

10.1021/om701059t

The research study on the reactivity of cationic (R-diimine)Pd-Me species with nitrogen-containing olefins, aiming to evaluate their potential for catalytic copolymerization with ethylene. The study focused on three nitrogen-containing olefins: allyl dimethyl amine, N-pentenylcarbazole, and N-allyl carbazole. The research concluded that while allyl dimethyl amine formed an inert five-membered chelate complex, N-pentenylcarbazole and N-allyl carbazole formed reactive three-membered chelate complexes after a chainwalking process.