2-Phenylindole

Base Information

• Chemical Name: 2-Phenylindole
• CAS No.: 948-65-2
• Deprecated CAS: 2222571-82-4
• Molecular Formula: C14H11N
• Molecular Weight: 193.248
• Hs Code.: 29309090
• European Community (EC) Number: 213-436-3
• NSC Number: 15776
• UNII: MQD44HV3P1
• DSSTox Substance ID: DTXSID8061343
• Nikkaji Number: J36.864D
• Wikipedia: 2-Phenylindole
• Wikidata: Q27194433
• ChEMBL ID: CHEMBL75756
• Mol file: 948-65-2.mol

Synonyms:alpha-phenylindole;alpha-phenylindole potassium salt

Chemical Property of 2-Phenylindole

Chemical Property:

• Appearance/Colour: off-white to beige or slightly green powder
• Vapor Pressure: 7.18E-07mmHg at 25°C
• Melting Point: 188-190 °C(lit.)
• Refractive Index: 1.5850 (estimate)
• Boiling Point: 419.9 °C at 760 mmHg
• PKA: 16.80±0.30(Predicted)
• Flash Point: 176.6 °C
• PSA: 15.79000
• Density: 1.156 g/cm³
• LogP: 3.83490
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: almost transparency in Methanol
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 193.089149355
• Heavy Atom Count: 15
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

2-Phenyl-1H-indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Indoles
• Canonical SMILES: C1=CC=C(C=C1)C2=CC3=CC=CC=C3N2
• Uses: Reactant for preparation of: ? ;Oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition1? ;Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators2? ;Organic light emitting diodes (OLEDs)3? ;Anti inflammatory agents4? ;Potential cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitors5? ;Agents for cancer and malaria therapy6? ;Antifungal and antibacterial agents7? ;Fluorescent probes8Reactant in:? ;Difluorohydroxylation reactions?? ;Mannich-type reactions? Phenylindole is a stabilizer in PVC-plastic products (α-phenylindole). Reactant for preparation of: Oxopyrrolidine analogs via iodine-catalyzed Markovnikov additionTryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsOrganic light emitting diodes (OLEDs)Anti inflammatory agentsPotential cyclooxygenase-1 (COX-1)/cyclooxygenase-2 (COX-2) inhibitorsAgents for cancer and malaria therapyAntifungal and antibacterial agentsFluorescent probesReactant in:Difluorohydroxylation reactions?Mannich-type reactions?

Technology Process of 2-Phenylindole

There total 597 articles about 2-Phenylindole 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: 83.0%

bromobenzene (108-86-1,52753-63-6) + N-(2-bromophenyl)-2,2,2-trifluoroacetamide (2727-71-1) + phenylacetylene (536-74-3) → 2-phenyl-indole (948-65-2) + 2,3-diphenyl-1H-indole (3469-20-3)

Guidance literature:

N-(2-bromophenyl)-2,2,2-trifluoroacetamide; phenylacetylene; With bis(benzonitrile)palladium(II) dichloride; caesium carbonate; XPhos; In N,N-dimethyl-formamide; at 80 ℃; for 1.2h; Inert atmosphere; Sealed tube;

bromobenzene; In N,N-dimethyl-formamide; at 80 ℃; for 2h; Reagent/catalyst; Time; regiospecific reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jo302679f

Reference yield: 74.0%

2-(benzotriazol-1-yl)acetophenone (127876-36-2) → 2-phenyl-indole (948-65-2) + aniline (62-53-3)

Guidance literature:

In acetonitrile; at 260.8 - 312.1 ℃; Kinetics;

DOI:10.1002/poc.717

Reference yield: 69.0%

N-benzyl-2-benzylaniline (851670-79-6) → acridine (260-94-6) + 2-phenyl-indole (948-65-2) + 2,3-diphenyl-1H-indole (3469-20-3)

Guidance literature:

at 450 ℃; for 0.666667h;

DOI:10.1002/jhet.5570450331

upstream raw materials:

3-phenyl-1H-indole

(E)-3-Ureido-but-2-enoic acid ethyl ester

2-phenyl-2,3-dihydro-1H-indole

phenyl(1-phenylethylidene)amine

Downstream raw materials:

2-phenylindole-3-acetic acid

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

(2-phenyl-indol-3-yl)-glyoxylic acid dimethylamide

(2-phenyl-indol-3-yl)-glyoxylic acid piperidide

Refernces

• 1、 Zakharova, Olga,Nevinsky, Georgy,Politanskaya, Larisa,Baev, Dmitry,Ovchinnikova, Ludmila,Tretyakov, Evgeny. "Evaluation of antioxidant activity and cytotoxicity of polyfluorinated diarylacetylenes and indoles toward human cancer cells". . . Retrieved 2019.
• 2、 Zou, Yun-Xiang,Liu, Xiao-Yan,Zhang, Jing,Yang, Hong-Li,Yang, Xin-Yue,Liu, Xiao-Ling,Chu, Yi-Wen,Chen, Long. "Synthesis of C2-Phosphorylated Indoles via Metal-Free 1,2-Phosphorylation of 3-Indolylmethanols with P(O)-H Species". . p. 5311 - 5316. Retrieved 2019.
• 3、 Ventura-Espinosa, David,Sabater, Sara,Mata, Jose A.. "Enhancement of gold catalytic activity and stability by immobilization on the surface of graphene". . p. 498 - 504. Retrieved 2017.
• 4、 Savva, Ioanna,Kalogirou, Andreas S.,Achilleos, Mariliz,Vasile, Eugenia,Koutentis, Panayiotis A.,Krasia-Christoforou, Theodora. "Evaluation of PVP/Au nanocomposite fibers as heterogeneous catalysts in indole synthesis". . . Retrieved 2016.
• 5、 Arai, Noriyoshi,Ohkuma, Takeshi. "Stereoselective Construction of Methylenecyclobutane-Fused Indolines through Photosensitized [2+2] Cycloaddition of Allene-Tethered Indole Derivatives". . p. 1506 - 1510. Retrieved 2019.
• 6、 Nikbakht, Ali,Balalaie, Saeed,Baghestani, Fatemeh,Rominger, Frank. "Efficient Synthesis of Indole Derivatives Containing the Tetrazole Moeity Utilizing an Ugi-Azide Post-Transformation Strategy". . p. 1892 - 1896. Retrieved 2018.
• 7、 Nguyen, Nguyen H.,Oh, Soo Min,Park, Cheol-Min,Shin, Seunghoon. "Ortho -selective C-H arylation of phenols with N -carboxyindoles under Br?nsted acid- or Cu(i)-catalysis". . p. 1169 - 1176. Retrieved 2022/02/02.
• 8、 Asensio, Gregorio,Cárcel, María,Olmos, Andrea,Ramírez De Arellano, Carmen,Sarmiento, Jeymy T.,Varea, Teresa. "Straightforward Synthesis of α-Chloromethylketimines Catalyzed by Gold(I). A Clean Way to Building Blocks". supporting information. p. 3114 - 3122. Retrieved 2022/03/14.