1-benzyl-5-bromo-1H-indole

Base Information

• Chemical Name: 1-benzyl-5-bromo-1H-indole
• CAS No.: 10075-51-1
• Molecular Formula: C15H12BrN
• Molecular Weight: 286.171
• NSC Number: 143237
• DSSTox Substance ID: DTXSID10301419
• Nikkaji Number: J931.353B
• Wikidata: Q82045334
• Mol file: 10075-51-1.mol

Synonyms:1-benzyl-5-bromo-1H-indole;1-Benzyl-5-bromoindole;10075-51-1;Indole, 1-benzyl-5-bromo-;N-Benzyl-5-bromoindole;NSC 143237;NSC143237;N-benzyl-5-bromoindole;SCHEMBL3861264;DTXSID10301419;MFCD04337704;AKOS015994508;NSC-143237;SS-3732;1-Benzyl-5-bromo-1H-indole, AldrichCPR;B6090;CS-0034510;FT-0707675;CBZ-1-AMINO-1-CYCLODECANECARBOXYLICACID;AR-527/42400121

Chemical Property of 1-benzyl-5-bromo-1H-indole

Chemical Property:

• Vapor Pressure: 4.79E-07mmHg at 25°C
• Melting Point: 93-95 °C
• Refractive Index: 1.631
• Boiling Point: 425.3 °C at 760 mmHg
• Flash Point: 211 °C
• PSA: 4.93000
• Density: 1.35 g/cm³
• LogP: 4.45210
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 285.01531
• Heavy Atom Count: 17
• Complexity: 249

Purity/Quality:

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

1-Benzyl-5-bromoindole ^*data from reagent suppliers

Safty Information:

• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN2C=CC3=C2C=CC(=C3)Br

Technology Process of 1-benzyl-5-bromo-1H-indole

There total 15 articles about 1-benzyl-5-bromo-1H-indole 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: 99.0%

5-bromo-1H-indole (10075-50-0) + benzyl bromide (100-39-0) → 1-benzyl-5-bromo-1H-indole (10075-51-1)

Guidance literature:

5-bromo-1H-indole; With sodium hydride; In dimethyl sulfoxide; mineral oil; at 20 ℃; Inert atmosphere; Schlenk technique;

benzyl bromide; In dimethyl sulfoxide; mineral oil; at 20 ℃; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.jmedchem.6b00478

Reference yield: 97.0%

5-bromo-1-benzylindoline (18359-64-3) → 1-benzyl-5-bromo-1H-indole (10075-51-1)

Guidance literature:

With tris(pentafluorophenyl)borate; In toluene; at 120 ℃; for 15h; under 75.0075 Torr; Inert atmosphere; Schlenk technique; Glovebox;

DOI:10.1002/anie.201606426

Reference yield: 90.0%

5-bromo-1H-indole (10075-50-0) + benzyl chloride (100-44-7) → 1-benzyl-5-bromo-1H-indole (10075-51-1)

Guidance literature:

With potassium hydroxide; In N,N-dimethyl-formamide; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.12.078

upstream raw materials:

5-bromo-1H-indole

benzyl alcohol

DBC

benzyl bromide

Downstream raw materials:

N-benzylindole

1-benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indole

1-[4-(1-benzyl-1H-indol-5-yl)phenyl]-1-ethanone

1-benzyl-5-[3-(trifluoromethoxy)phenyl]-1H-indole

Refernces

• 1、 Wang, Yi,Yuan,Xing, Chun-Hui,Lu, Long. "Trifluoromethanesulfonic acid-catalyzed solvent-free bisindolylation of trifluoromethyl ketones". . p. 1045 - 1048. Retrieved 2014.
• 2、 Nguyen, Hung M.,Golantsov, Nikita E.,Golubenkova, Alexandra S.,Rybakov, Victor B.,Voskressensky, Leonid G.. "Three-component reactions of 3-arylidene-3h-indolium salts, isocyanides and amines". . . Retrieved 2021.
• 3、 Kahar, Nilesh,Jadhav, Pankaj,Reddy, R. V. Ramana,Dawande, Sudam. "A rhodium(ii) catalysed domino synthesis of azepino fused diindoles from isatin tethered: N -sulfonyl-1,2,3-triazoles and indoles". . p. 1207 - 1210. Retrieved 2020.
• 4、 McGough, John S.,Cid, Jessica,Ingleson, Michael J.. "Catalytic Electrophilic C?H Borylation Using NHC?Boranes and Iodine Forms C2-, not C3-, Borylated Indoles". . p. 8180 - 8184. Retrieved 2017.
• 5、 Evans, David A.,Fandrick, Keith R.,Song, Hyun-Ji. "Enantioselective Friedel-Crafts alkylations of α,β-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes". . p. 8942 - 8943. Retrieved 2005.
• 6、 Shieh, Wen-Chung,Lozanov, Mario,Loo, Mauricio,Repi?, Oljan,Blacklock, Thomas J.. "DABCO- and DBU-accelerated green chemistry for N-, O-, and S-benzylation with dibenzyl carbonate". . p. 4563 - 4565. Retrieved 2003.
• 7、 Borghs, Jannik C.,Zubar, Viktoriia,Zubar, Viktoriia,Azofra, Luis Miguel,Sklyaruk, Jan,Rueping, Magnus,Rueping, Magnus. "Manganese-Catalyzed Regioselective Dehydrogenative C-versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation". . p. 4222 - 4227. Retrieved 2020/06/04.