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193984 Aldrich

1-Methylindole

≥97%

Synonym: NSC 212534

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
assay   ≥97%
refractive index   n20/D 1.606(lit.)
bp   133 °C/26 mmHg(lit.)
density   1.051 g/mL at 20 °C(lit.)

Description

Packaging

5, 25 g in glass bottle

Application

1-Methylindole was used in the determination of association constant for the electron-donor-acceptor complexes of 1-methylindole with 1-(2,4,6-trinitrophenyl) propan-2-one1.

Reactant for preparation of:
• Pharmaceutically active 2-oxo-1-pyrrolidine analogues
• Non-receptor tyrosine kinase (Src kinase) inhibitors
• PET agents for imaging of protein kinase C (PKC)
• Ynediones as highly reactive Michael systems
• Anticancer agents
• Polycyclic derivatives of indoles
• PET agents for imaging of glycogen synthase kinase-3 (GSK-3)
• Anti-prion disease agents
• Bisindole derivatives with antihyperlipidemic activity
• PET cancer imaging agents

General description

1-Methylindole undergoes Au(III)/TPPMS-catalyzed benzylation reaction with benzhydryl and benzylic alcohols2.

Price and Availability


Palau’Chlor

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Safety & Documentation

Safety Information

RIDADR 
UN 3334
WGK Germany 
3
Flash Point(F) 
235.4 °F
Flash Point(C) 
113 °C

Protocols & Articles

Peer-Reviewed Papers

References

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1. Association constants for the electron-donor-acceptor complexes of indole and 1-methylindole with 1-(2, 4, 6-trinitrophenyl) propan-2-one from nuclear magnetic resonance shift measurements. An anomalous scatchard plot. Chudek JA, et al. J. Chem. Soc., Faraday 84(4), 1145-52, (1988)

2. Au(III)/TPPMS-catalyzed benzylation of indoles with benzylic alcohols in water. Hikawa H, Suzuki H, and Azumaya I J. Org. Chem. 78(23), 12128-35, (2013)

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Room temperature palladium-catalyzed 2-arylation of indoles. Deprez NR, Kalyani D, Krause A, et al. J. Am. Chem. Soc. 128(15), 4972-3, (2006)

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Direct palladium-catalyzed C-2 and C-3 arylation of indoles: a mechanistic rationale for regioselectivity. Lane BS, Brown MA, and Sames D J. Am. Chem. Soc. 127(22), 8050-7, (2005)

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Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids. Banwell MG, Ma X, Taylor RM, et al. Org. Lett. 8(21), 4959-61, (2006)

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Photodissociation dynamics of N-methylindole, N-methylpyrrole, and anisole. Tseng CM, Lee YT, and Ni CK J. Phys. Chem. A 113(16), 3881-5, (2009)

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Chernyak, N.; et al. ARKIVOC, 76, (2011)

Direct alkylation of indoles and amines by tert-enamides: facile access to pharmaceutically active 2-oxo-1-pyrrolidine analogues. Jiang, R.; et al. Org. Biomol. Chem. 9, 5659, (2011)

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Three-component synthesis of ynediones by a glyoxylation/Stephens-Castro coupling sequence. Merkul, E.; et al. Angew. Chem. Int. Ed. Engl. 50, 2966, (2011)

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[11C]enzastaurin, the first design and radiosynthesis of a new potential PET agent for imaging of protein kinase C. Wang, M.; et al. Bioorg. Med. Chem. Lett. 21, 1649, (2011)

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Synthesis of novel indolyl-1,2,4-triazoles as potent and selective anticancer agents. Kumar, D.; et al. Chem. Biol. Drug Des. 77, 182, (2011)

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Structure-activity relationship refinement and further assessment of indole-3-glyoxylamides as a lead series against prion disease. Thompson, M. J.; et al. ChemMedChem 6, 115, (2011)

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The first synthesis of [(11)C]SB-216763, a new potential PET agent for imaging of glycogen synthase kinase-3 (GSK-3). Wang, M.; et al. Bioorg. Med. Chem. Lett. 21, 245, (2011)

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The first design and synthesis of [11C]MKC-1 ([11C]Ro 31-7453), a new potential PET cancer imaging agent. Wang, M.; et al. Nucl. Med. Biol. 37, 763, (2010)

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Synthesis and antihyperlipidemic activity of novel coumarin bisindole derivatives. Sashidhara, K. V.; et al. Bioorg. Med. Chem. Lett. 20, 6504, (2010)

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3-substitued indoles: one-pot synthesis and evaluation of anticancer and Src kinase inhibitory activities. Rao, V. K.; et al. Bioorg. Med. Chem. Lett. 21, 3511, (2011)

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Spectroscopic characterization studies of 1-methyl indole with benzene derivatives. Bakkialakshmi S, Shanthi B, and Shanthi M Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 77(1), 179-83, (2010)

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Degradation of substituted indoles by an indole-degrading methanogenic consortium. Gu JD and Berry DF Appl. Environ. Microbiol. 57(9), 2622-7, (1991)

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Beil. 20,V,7,12

FT-IR 1 (2), 653:B / FT-IR 2 (3), 3570:B / FT-NMR 1 (3), 121:B / IR-Spectra (3), 1242:B / NMR-Reference 2 (2), 519:B / RegBook 1 (2), 2401:B / Sigma FT-IR 1 (2), 737:A / Structure Index 1, 381:B:1 / Vapor Phase 3, 1497:B

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