15258-46-5

Basic information

• Product Name: 4-methyl-N-(prop-2-en-1-yl)aniline
• Synonyms: p-Toluidine, N-allyl-
• CAS NO: 15258-46-5
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.2169
• Mol File: 15258-46-5.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 235.7°C at 760 mmHg
• Flash Point: 96°C
• Density: 0.96g/cm³
• Vapor Pressure: 0.0493mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: 4-methyl-N-(prop-2-en-1-yl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-N-(prop-2-en-1-yl)aniline(15258-46-5)
• EPA Substance Registry System: 4-methyl-N-(prop-2-en-1-yl)aniline(15258-46-5)

Safety Data

• Hazardous Substances Data: 15258-46-5(Hazardous Substances Data)

Upstream product

• 7575-57-7 allyl benzenesulfonate 
• 106-49-0 p-toluidine 
• 107-18-6 allyl alcohol 
• 2101-86-2 p-methylazidobenzene 
• 106-95-6 allyl bromide 
• 22774-64-7 N-propargyl-4-methylaniline 
• 3481-07-0 N-allyl-N-methyl-4-methylaniline 
• 1384753-11-0 C₁₀H₁₅NO 
• 62-23-7 4-nitro-benzoic acid 
• 1172142-53-8 N-allyl-N-(4-methylphenyl)-2-nitrobenzenesulfonamide 
• 14618-59-8 N-(tert-butoxycarbonyl)-4-methylaniline 
• 556-56-9 allyl iodid 
• 6728-21-8 allyl mesylate 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 73396-95-9 2-bromo-4-methyl-N-allylaniline 
• 913169-20-7 N-allyl-N-benzyl-4-methylaniline 
• 90874-56-9 (±)-2,5-dimethylindoline 
• 1172142-65-2 methyl 2-[N-allyl-N-(4-methylphenyl)sulfamoyl]acetate 
• 1202021-50-8 C₁₇H₂₂BrN 
• 1202021-55-3 C₂₁H₂₂BrN 
• 1620758-86-2 N-allyl-N-(4-methylphenyl)ethenesulfonamide 
• 1620758-97-5 2-(4-methylphenyl)-2,3-dihydroisothiazole 1,1-dioxide 
• 199929-31-2 3-hydroxy-N-(4-methylphenyl)propanamide 
• 66236-12-2 N-(2-allyl-4-methylphenyl)methanesulfonamide 
• 340011-47-4 N-allyl N-(4-methylphenyl)acrylamide 
• 167558-64-7 1-(4-methyl-phenyl)-3-methyl-1H-indole 

Relevant articles and documents

Pentacoordinated Carboxylate π-Allyl Nickel Complexes as Key Intermediates for the Ni-Catalyzed Direct Amination of Allylic Alcohols

Direct amination of allylic alcohols with primary and secondary amines catalyzed by a system made of [Ni(1,5-cyclooctadiene)2] and 1,1′-bis(diphenylphosphino)ferrocene was effectively enhanced by adding nBu4NOAc and molecular sieves, affording the corresponding allyl amines in high yield with high monoallylation selectivity for primary amines and high regioselectivity for monosubstituted allylic alcohols. Such remarkable additive effects of nBu4NOAc were elucidated by isolating and characterizing some nickel complexes, manifesting the key role of a charge neutral pentacoordinated η3-allyl acetate complex in the present system, in contrast to usual cationic tetracoordinated complexes earlier reported in allylic substitution reactions.

Synthesis of functionalized indoles via palladium-catalyzed cyclization of N-(2-allylphenyl) benzamide: A method for synthesis of indomethacin precursor

We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin.

Synthesis of Benzofuran and Indole Derivatives Catalyzed by Palladium on Carbon

Benzofurans and indoles are key moieties in many natural products and pharmaceuticals. Herein, we describe a cheap and easy-to-execute strategy for the synthesis of benzofurans and indoles, employing Pd/C as the promoter. A variety of substituted allyl-anilines and allyl-phenols were converted into the desired products in good to excellent yields. Recycling of Pd/C was possible up to five cycles, keeping similar levels of reactivity.