17771-42-5

Basic information

• Product Name: 3-(dimethylallyl)indole
• Synonyms: 3-(dimethylallyl)indole
• CAS NO: 17771-42-5
• Molecular Formula: C₁₃H₁₅N
• Molecular Weight: 0
• Mol File: 17771-42-5.mol

Chemical Properties

• Boiling Point: 310.6°Cat760mmHg
• Flash Point: 130.5°C
• Appearance: /
• Density: 1.028g/cm³
• Vapor Pressure: 0.00109mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: 3-(dimethylallyl)indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(dimethylallyl)indole(17771-42-5)
• EPA Substance Registry System: 3-(dimethylallyl)indole(17771-42-5)

Safety Data

• Hazardous Substances Data: 17771-42-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H15N/c1-4-13(2,3)11-9-14-12-8-6-5-7-10(11)12/h4-9,14H,1H2,2-3H3

Upstream product

• 120-72-9 indole 
• 870-63-3 prenyl bromide 
• 552-89-6 2-nitro-benzaldehyde 
• 78-79-5 isoprene 
• 153942-69-9 3-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-indole 
• 556-82-1 3-methyl-2-buten-1-ol 
• 102210-80-0 1-(benzenesulfonyl)-3-(β,β-dimethylacrylyl)indole 
• 99655-68-2 3-bromo-1-phenylsulfonyl indole 
• 16886-08-1 1-allylindole 
• 1484-27-1 3-bromoindole 
• 40899-73-8 N-tert-butyldimethylsilylindole 
• 88927-34-8 methyl (3-methylbut-2-en-1-yl) carbonate 
• 102210-79-7 3-(3-methylbut-2-en-1-yl)-1-(phenylsulfonyl)-1H-indole 
• 50615-00-4 β-(β,β-dimethylacrylyl)indole 

Downstream Products

• 102210-79-7 3-(3-methylbut-2-en-1-yl)-1-(phenylsulfonyl)-1H-indole 

Relevant articles and documents

Unprecedented total synthesis of bruceolline D, E, and H

Single pot strategy of wittig olefination-Claisen rearrangement has been employed to obtain 3-prenylated indoles. The resulting indoles on the consecutive sequence of epoxidation, cyclization and further oxidation afforded short, protecting group free tot

Catalytic Prenylation and Reverse Prenylation of Indoles with Isoprene: Regioselectivity Manipulation through Choice of Metal Hydride

The basic industrial feedstock isoprene was employed as a building block to install prenyl and reverse-prenyl groups onto indoles. The regioselectivity can be manipulated by the choice of metal hydride. Reverse-prenylated indoles were attained with high selectivity when using Rh?H. By switching to a Pd?H catalyst, selectivity toward prenylated indoles was achieved. This regiodivergent method also features high atom economy without stoichiometric byproduct formation.

Isoprene: A Promising Coupling Partner in C-H Functionalizations

Five-carbon dimethylallyl units, such as prenyl and reverse-prenyl, are widely distributed in natural indole alkaloids and terpenoids. In conventional methodologies, these valuable motifs are often derived from substrates bearing leaving groups, but these

Method for introducing isopentenyl to C3 site of indole

The invention relates to a method for introducing isopentenyl into the C3 site of indole. Specifically, indole and isoprene are used as raw materials, and isopentenyl can be introduced into the C3 site of indole with high selectivity under the promotion of a palladium catalyst/phosphine ligand. The method has the following advantages: isoprene is a green bulk chemical, is simple and easily available, and is low in price; simple indole can participate in the reaction, and NH does not need to be protected; and leaving groups are not needed, and the atom economy is high.

An efficient molybdenum(VI)-catalyzed direct substitution of allylic alcohols with nitrogen, oxygen, and carbon nucleophiles

Direct nucleophilic substitution of allylic alcohols with various nitrogen, oxygen, and carbon nucleophiles catalyzed by MoO2(acac)2 was realized. The corresponding products were obtained in moderate-to-excellent yields. Studies of t

Allylation of N-Heterocycles with allylic alcohols employing self-assembling palladium phosphane catalysts

The first palladium catalyst system that allows the direct allylation of indoles with allylic alcohols as substrates with water being the only byproduct is presented. The application of self-assembing ligands based on complementary hydrogen bonding was the key to success.

Electrophilic allylations and benzylations of indoles in neutral aqueous or alcoholic solutions

(Chemical Equation Presented) Indoles are allylated and benzylated in moderate to quantitative yield when stirred with allyl and benzyl halides in 80% aqueous acetone in the presence of NH4HCO3 at room temperature.

Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane

Under palladium catalysis, Et3B nicely promotes allyl alcohols to undergo C3-selective allylation of indoles and tryptophan; the yields range 75-95%. Copyright

New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic substitution: Controlling the regioselectivity

(Chemical Equation Presented) A systematic study addressed toward the optimization of the Pd-catalyzed alkylation of indoles by allylic carbonates is presented. The protocol uses a catalytic amount of [PdCl(π-allyl)] 2/phosphine as a promoting

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.