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Chemistry
Heterocyclic Building Blocks
Indoles
5-Methyl-2-phenyl-1H-indole
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
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[ CAS No. 13228-36-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 13228-36-9
Chemical Structure| 13228-36-9
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Quality Control of [ 13228-36-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 13228-36-9 ]

Product Details of [ 13228-36-9 ]

CAS No. :13228-36-9 MDL No. :MFCD00022700
Formula : C15H13N Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 207.27 Pubchem ID :-
Synonyms :

Safety of [ 13228-36-9 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H318-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13228-36-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 13228-36-9 ]

[ 13228-36-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 583-68-6 ]
  • [ 98-81-7 ]
  • [ 13228-36-9 ]
YieldReaction ConditionsOperation in experiment
85% With sodium t-butanolate In toluene at 215℃; microwave irradiation;
62% With sodium t-butanolate; DavePhos In toluene at 100℃; for 20h;
Reference： [1]Shore, Gjergji; Morin, Sylvie; Mallik, Debasis; Organ, Michael G. [Chemistry - A European Journal, 2008, vol. 14, # 4, p. 1351 - 1356]
[2]Barluenga, Jose; Fernandez, M. Alejandro; Aznar, Fernando; Valdes, Carlos [Chemistry - A European Journal, 2005, vol. 11, # 8, p. 2276 - 2283]
  • 2
  • [ 13228-36-9 ]
  • [ 71999-74-1 ]
  • [ 1610423-37-4 ]
Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 3567 - 3571
  • 3
  • [ 13228-36-9 ]
  • [ 17852-28-7 ]
YieldReaction ConditionsOperation in experiment
55% With oxygen; caesium carbonate In dimethyl sulfoxide at 140℃; for 8h; 2. Typical procedure for the synthesis of 2a General procedure: A solution of 2-phenylindole (1a, 97 mg, 0.5 mmol) and Cs2CO3 (326 mg, 1.0 mmol) in DMSO (1.5 mL) was heated to 140 °C for 8 h under O2 balloon atmosphere. After the usual aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 10:1), 2-aminobenzophenone (2a) was obtained as a yellow solid, 59 mg (60 %). Other compounds were prepared similarly, and the spectroscopic data of compounds 2a-l, 4 and 5 are as follows.
Reference： [1]Yu, Jin; Moon, Hye Ran; Min, Beom Kyu; Kim, Jae Nyoung [Bulletin of the Korean Chemical Society, 2016, vol. 37, # 6, p. 893 - 897]
  • 4
  • [ 591-50-4 ]
  • [ 614-96-0 ]
  • [ 13228-36-9 ]
YieldReaction ConditionsOperation in experiment
89% With norborn-2-ene; bis(acetonitrile)palladium(II) chloride; potassium carbonate In N,N-dimethyl acetamide; water monomer at 70℃; regioselective reaction; 2. General procedure for 2-arylation of free (N-H) indoles General procedure: A high pressure tube equipped with a magnetic stirring bar was charged with indole substrate (0.2mmol, 1 equiv.), norbornene (0.4mmol, 2 equiv.), the base (0.4mmol, 2 equiv. K2CO3 or 2 equiv. KHCO3, as indicated),, and PdCl2(MeCN)2 (0.02mmol, 10 mol %). A solution of water (0.5 M) in DMA (1mL) was added via syringe, and then the aryl iodide (0.4mmol, 2 equiv.) was added via syringe. The reaction mixture was then placed in a preheated oil bath at 70 °C (or 90 °C, as indicated). Vigorous stirring was applied. The reaction was monitored by TLC. Upon completion, the reaction mixture was cooled to room temperature, diluted with EtOAc, and filtered. The filtrate was extracted with H2O (3 times) and brine, the organic phase was concentrated in vacuum to remove the solvent. The residue was directly submitted to flash column chromatography to afford the 2-arylindole product. The spectral data of the products were in accordance with those reported in the literature1.
63% With (9-hydroxydiamant-4-yl)phosphine; palladium diacetate; Potassium bicarbonate In water monomer at 100℃; for 30h; regioselective reaction;
With norborn-2-ene; water monomer; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 70℃;
With norborn-2-ene; bis(acetonitrile)palladium(II) chloride; potassium carbonate In N,N-dimethyl acetamide; water monomer at 70℃;

Reference： [1]Gao, Yadong; Zhu, Wangying; Yin, Long; Dong, Bo; Fu, Jingjing; Ye, Zhiwen; Xue, Fengtian; Jiang, Chao [Tetrahedron Letters, 2017, vol. 58, # 23, p. 2213 - 2216]
[2]Moncea, Oana; Poinsot, Didier; Fokin, Andrey A.; Schreiner, Peter R.; Hierso, Jean-Cyrille [ChemCatChem, 2018, vol. 10, # 13, p. 2915 - 2922]
[3]Chen, Yu-Jue; Chen, Yuan; Ding, Xuan; Guan, Zhi; He, Yan-Hong; Lu, Fo-Yun [Chemical Communications, 2020, vol. 56, # 4, p. 623 - 626]
[4]Zhao, Yong-Long; An, Jian-Xiong; Yang, Fen-Fen; Guan, Xiang; Fu, Xiao-Zhong; Li, Zong-Qin; Wang, Da-Peng; Zhou, Meng; Yang, Yuan-Yong; He, Bin [Advanced Synthesis and Catalysis, 2022, vol. 364, # 7, p. 1277 - 1285]
  • 5
  • [ 13228-36-9 ]
  • [ 1538-08-5 ]
  • 3,3'-(2,2,2-trifluoroethyl-1-yl)bis(5-methyl-2-phenyl-1H-indole) [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With copper(I) sulfide; di-tert-butyl peroxide; potassium tert-butylate; magnesium triflate; In 1,2-dichloro-ethane; at 120℃; for 12h;Inert atmosphere; Sealed tube; Under a nitrogen atmosphere, add 0.2 mmol of 2-phenyl-5-methylindole to a 25mL reaction tube with a polytetrafluoroethylene magnetic stirrer.0.24 mmol of trifluoroacetylhydrazine, 0.7 mmol of potassium tert-butoxide, 0.3 mmol of di-tert-butyl peroxide (DTBP), 0.05 mmol Cu2S, 0.2mmol of magnesium trifluoromethanesulfonate was finally added with 1-2mL of solvent 1,2-dichloroethane, and the reaction was stirred in a closed system at 120 C for 12 hours and then cooled to room temperature.The reaction mixture was diluted with ethyl acetate, washed with saturated NaHCO3 solution and saturated brine, and the organic phase was dried over anhydrous MgSO4, filtered and the solvent was removed by rotary evaporation, using n-pentane and ethyl acetate as eluents, 3,3'-(2,2,2-trifluoroethyl)bis (5-methyl-2-phenyl-1H-indole) was isolated by silica gel column chromatography (isolated yield 83%)
Reference： [1]Patent: CN110272370,2019,A .Location in patent: Paragraph 0039; 0040; 0057; 0058; 0063; 0064

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