16886-09-2

Basic information

• Product Name: 3-(2-PROPENYL)INDOLE
• Synonyms: 3-(2-PROPENYL)INDOLE;3-ALLYL-1H-INDOLE;3-Allylindole;3-(prop-2-en-1-yl)-1h-indole;3-prop-2-enyl-1H-indole
• CAS NO: 16886-09-2
• Molecular Formula: C₁₁H₁₁N
• Molecular Weight: 157.21174
• Mol File: 16886-09-2.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 297.9°Cat760mmHg
• Flash Point: 127.6°C
• Appearance: /
• Density: 1.074g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: 3-(2-PROPENYL)INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-PROPENYL)INDOLE(16886-09-2)
• EPA Substance Registry System: 3-(2-PROPENYL)INDOLE(16886-09-2)

Safety Data

• Hazardous Substances Data: 16886-09-2(Hazardous Substances Data)

Usage

General Description

3-(2-Propenyl)indole, also known as β-Carbolines, is a chemical compound that belongs to the category of indole alkaloids. It is a naturally occurring compound found in various plants, such as the Peganum harmala (Syrian Rue) and the Ayahuasca vine. It is known for its psychoactive and hallucinogenic properties and has been used in traditional medicine and shamanic rituals for its mind-altering effects. β-Carbolines have been studied for their potential therapeutic applications in treating various neurological disorders, including depression and anxiety. Additionally, they have been investigated for their potential anti-cancer and anti-inflammatory properties. However, it is important to note that the use of β-Carbolines should be approached with caution due to their potent psychoactive effects.

InChI:InChI=1/C11H11N/c1-2-5-9-8-12-11-7-4-3-6-10(9)11/h2-4,6-8,12H,1,5H2

Upstream product

• 120-72-9 indole 
• 591-87-7 Allyl acetate 
• 107-18-6 allyl alcohol 
• 106-95-6 allyl bromide 
• 1746-13-0 allyl phenyl ether 
• 63212-36-2 o-(3-butenyl)phenyl isocyanide 
• 23542-51-0 5-nitropent-1-ene 
• 100-63-0 phenylhydrazine 
• 1307800-88-9 (-)-(S)-3-benzyl-4-[(1H-indol-3-yl)methyl]-1,3-thiazolidine-2-thione 
• 271-26-1 3H-indole 
• 133-32-4 4-indol-3-yl-butyric acid 
• 13884-15-6 (Indol-1-yl)magnesium iodide 
• 107-05-1 3-chloroprop-1-ene 
• 18344-49-5 1-indolyllithium 

Downstream Products

• 6547-98-4 3-indol-3-yl-propane-1,2-diol 
• 1134199-11-3 N-(2-nitrobenzenesulfonyl)-2-(1H-3-indolylmethyl)aziridine 
• 133-32-4 4-indol-3-yl-butyric acid 

Relevant articles and documents

1,4-pentadienyl-3-sulfonamides: frameworks for disfavored radical cascade cyclizations.

[reaction: see text]. 1,4-pentadienyl-3-sulfonamides afford products including those resulting from disfavored 5-endo-trig reactions when subjected to radical cyclization conditions. Products resulting from pathways featuring 4-exo-trig cyclizations are also detected, even when the 4-exo-trig reaction leads to a highly strained bicyclo[3.2.0] ring system.

Sodium Perborate: A Facile Catalyst for Allylation of Active Centers

An efficient and ecofriendly allylation of O-H, N-H, and C-H groups has been achieved successfully with the reaction of allyl bromide by using sodium perborate as a new catalyst in aqueous media. The advantage of this method is operationally simple, short reaction time, good yield, and simple workup conditions over the previously reported conventional methods such as amination, oxyalkylation reactions of allyl bromide, and Friedel-Crafts allylation chemistry.

Zinc-mediated Barbier reactions of pyrrole and indoles: A new method for the alkylation of pyrrole and indoles

Pyrrole and indoles react smoothly with alkyl halides such as allyl bromide, prenyl bromide, crotyl bromide and propargyl bromide in the presence of zinc metal in THF to afford the corresponding 3- and 2-alkyl pyrrole and 3-alkyl indole derivatives in good yields with high regioselectivity.

Synthesis of allyl cyanamides and N-cyanoindoles via the palladium-catalyzed three-component coupling reaction

The palladium-catalyzed three-component coupling reaction (TCCR) of aryl isocyanides, allyl methyl carbonate, and trimethylsilyl azide was conducted in the presence of Pd2(dba)3·CHCl3 (2.5 mol %) and dppe (1,2-bis(diphenyl

A Combined Tamaru Allylation/Olefin Cross-Metathesis Approach for the Total Syntheses of (±)-Paniculidine B, (±)-Paniculidine C, and 2-Methylcarbazole

A concise approach to the total syntheses of racemic paniculidines B and C is described. The route features a combined Tamaru allylation/olefin cross-metathesis sequence for the regiocontrolled synthesis of prenylindole intermediates. In addition, we report a transformation of the prenylated indole into 2-methylcarbazole catalyzed by sulfonic acid-functionalized silica gel.

Diastereoselective Allylation of Aldehydes by Dual Photoredox and Chromium Catalysis

Herein, we report the redox-neutral allylation of aldehydes with readily available electron-rich allyl (hetero-) arenes, β-alkyl styrenes and allyl-diarylamines. This process was enabled by the combination of photoredox and chromium catalysis, which allowed a range of homoallylic alcohols to be prepared with high levels of selectivity for the anti diastereomer. Mechanistic investigations support the formation of an allyl chromium intermediate from allylic C(sp3)-H bonds and thus significantly extends the scope of the venerable Nozaki-Hiyama-Kishi reaction.

Total Synthesis of Isodihydrokoumine, (19 Z)-Taberpsychine, and (4 R)-Isodihydroukoumine N4-Oxide

We report the total synthesis of the natural products isodihydrokoumine and (19Z)-taberpsychine in 11 steps each and (4R)-isodihydrokoumine N4-oxide in 12 steps from commercially available starting materials. The key reactions include an intramolecular [3 + 2] nitrone cycloaddition and Lewis acid mediated cyclizations of a common intermediate to provide the core structures of either taberpsychine or isodihydrokoumine.