1-benzyl-1H-indole-3-carbaldehyde

Base Information

• Chemical Name: 1-benzyl-1H-indole-3-carbaldehyde
• CAS No.: 10511-51-0
• Molecular Formula: C16H13 N O
• Molecular Weight: 235.285
• Hs Code.: 2933990090
• European Community (EC) Number: 622-896-8
• NSC Number: 95434
• DSSTox Substance ID: DTXSID20294242
• Nikkaji Number: J709.087K
• Wikidata: Q82033432
• ChEMBL ID: CHEMBL1775116
• Mol file: 10511-51-0.mol

Synonyms:1-benzyl-1H-indole-3-carbaldehyde;10511-51-0;1-benzylindole-3-carbaldehyde;1-Benzylindole-3-carboxaldehyde;1-Benzyl-1H-indole-3-carboxaldehyde;MFCD00022894;1-Benzyl-3-indolylaldehyde;NSC95434;1H-Indole-3-carboxaldehyde,1-(phenylmethyl)-;1-benzylindol-3-carboxaldehyde;SCHEMBL1418988;CHEMBL1775116;1-benzyl-3-indole carboxaldehyde;DTXSID20294242;OXCITQLDOUGVRZ-UHFFFAOYSA-N;BBL009185;NSC-95434;STK409632;1-phenylmethyl-indole-3-carboxaldehyde;AKOS000100223;AM10038;PS-7661;BB 0217312;CS-0116564;FT-0607386;EN300-00958;1h-indole-3-carboxaldehyde, 1-(phenylmethyl)-;D85426;W-204544;Z56785554;F0266-0929

Chemical Property of 1-benzyl-1H-indole-3-carbaldehyde

Chemical Property:

• Vapor Pressure: 6.19E-08mmHg at 25°C
• Melting Point: 107℃
• Boiling Point: 439.8°Cat760mmHg
• Flash Point: 219.8°C
• PSA: 22.00000
• Density: 1.1g/cm³
• LogP: 3.50210
• Storage Temp.: −20°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 235.099714038
• Heavy Atom Count: 18
• Complexity: 285

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Benzylindole-3-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,C,Xi
• Hazard Codes: Xn,C,Xi
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN2C=C(C3=CC=CC=C32)C=O
• Uses: reactant in preparation of inhibitor of the C-terminal domain of RNA polymerase II 1 reactant in Nazarov type electrocyclization 2 reactant in preparation inhibitors of Bcl-2 family of proteins 3 reactant for Mannich type coupling with aldehydes and secondary amines. reactant in preparation of inhibitor of the C-terminal domain of RNA polymerase IIreactant in Nazarov type electrocyclizationreactant in preparation inhibitors of Bcl-2 family of proteinsreactant for Mannich type coupling with aldehydes and secondary amines

Technology Process of 1-benzyl-1H-indole-3-carbaldehyde

There total 39 articles about 1-benzyl-1H-indole-3-carbaldehyde 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: 100.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) → 1-Benzylindole-3-carboxaldehyde (10511-51-0)

Guidance literature:

Indole-3-carboxaldehyde; With sodium hydride; In acetonitrile;

benzyl halide; In acetonitrile;

DOI:10.1016/j.ejmech.2010.08.004

Reference yield: 99.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + benzyl bromide (100-39-0) → 1-Benzylindole-3-carboxaldehyde (10511-51-0)

Guidance literature:

Indole-3-carboxaldehyde; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.ejmech.2014.04.005

Reference yield: 95.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + benzyl chloride (100-44-7) → 1-Benzylindole-3-carboxaldehyde (10511-51-0)

Guidance literature:

Indole-3-carboxaldehyde; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

benzyl chloride; at 0 - 20 ℃;

DOI:10.1055/s-0041-1737275

upstream raw materials:

Indole-3-carboxaldehyde

benzyl bromide

benzyl chloride

1-benzyl-2-bromo-1H-indole-3-carboxyaldehyde

Downstream raw materials:

1-(1-Benzyl-1H-indol-3-yl)-1-(5-methoxypyridin-2-yl)-methanol

Methyl (+/-)-α-(1-phenylmethyl-3-indolylmethyl)amino-(3-trifluoromethylphenyl) acetate

Methyl (R)-α-(1-phenylmethyl-3-indolylmethyl)aminophenylacetate

Methyl (S)-α-(1-phenylmethyl-3-indolylmethyl)aminophenylacetate

Refernces

• 1、 Wang, Qing-Dong,Yang, Jin-Ming,Fang, Dong,Ren, Jiangmeng,Zeng, Bu-Bing. "Iodine-catalyzed C3-formylation of indoles using hexamethylenetetramine and air". . p. 2877 - 2880. Retrieved 2017.
• 2、 Milen, Matyas,Gruen, Alajos,Balint, Erika,Dancso, Andras,Keglevich, Gyoergy. "Solid-liquid phase alkylation of n-heterocycles: Microwave-assisted synthesis as an environmentally friendly alternative". . p. 2291 - 2301. Retrieved 2010.
• 3、 Elsayed, Mohamed S. A.,Zeller, Matthias,Cushman, Mark. "Synthesis of indolo[4,3-bc]phenanthridine-6,11(2H,12H)-diones using the schiff base–homophthalic anhydride cyclization reaction". . p. 1902 - 1908. Retrieved 2016.
• 4、 Pannipara, Mehboobali,Asiri, Abdullah M.,Alamry, Khalid A.,Arshad, Muhammad N.,El-Daly, Samy A.. "Synthesis, spectral behaviour and photophysics of donor-acceptor kind of chalcones: Excited state intramolecular charge transfer and fluorescence quenching studies". . p. 1893 - 1902. Retrieved 2015.
• 5、 Benmohammed, Abdelmadjid,Djafri, Ayada,Kadiri, Mokhtaria,Khoumeri, Omar,Louail, Ahmed Amine,Rekiba, Nawel,Sehanine, Yassine,Terme, Thierry,Vanelle, Patrice. "Synthesis and antimicrobial activities of new thiosemicarbazones and thiazolidinones in indole series". . p. 977 - 986. Retrieved 2021.
• 6、 Chereddy, Narendra Reddy,Korrapati, Purna Sai,Thennarasu, Sathiah,Mandal, Asit Baran. "Tuning copper(ii) ion selectivity: The role of basicity, size of the chelating ring and orientation of coordinating atoms". . p. 12873 - 12877. Retrieved 2013.
• 7、 Chadha, Navriti,Silakari, Om. "Identification of low micromolar dual inhibitors for aldose reductase (ALR2) and poly (ADP-ribose) polymerase (PARP-1) using structure based design approach". . p. 2324 - 2330. Retrieved 2017.
• 8、 Deng, Wenting,Wang, Lanying,Wang, Yunxia,Zhao, Junlong,Jia, Hongliang. "New hexamethine indothia-cyanines: Synthesis and photophysical properties as well as both antitumor activity and imaging". . . Retrieved 2021.
• 9、 Balakrishnan, Nithya,Haribabu, Jebiti,Eshaghi Malekshah, Rahime,Swaminathan, Srividya,Balachandran, Chandrasekar,Bhuvanesh, Nattamai,Aoki, Shin,Karvembu, Ramasamy. "Effect of N-benzyl group in indole scaffold of thiosemicarbazones on the biological activity of their Pd(II) complexes: DFT, biomolecular interactions, in silico docking, ADME and cytotoxicity studies". . . Retrieved 2022/01/26.
• 10、 Arcadi, Antonio,Calcaterra, Andrea,Chiarini, Marco,Fabrizi, Giancarlo,Fochetti, Andrea,Goggiamani, Antonella,Iazzetti, Antonia,Marrone, Federico,Marsicano, Vincenzo,Serraiocco, Andrea. "Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids". supporting information. p. 741 - 753. Retrieved 2021/11/26.