28144-67-4

Basic information

• Product Name: 1-phenyl-1-aminomethylethene
• Synonyms: 1-phenyl-1-aminomethylethene;2-Phenyl-allylamine
• CAS NO: 28144-67-4
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.19
• Mol File: 28144-67-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 54-56 °C(Solv: hexane (110-54-3); ligroine (8032-32-4))
• Boiling Point: 220.9°Cat760mmHg
• Flash Point: 91.5°C
• Appearance: /
• Density: 0.963g/cm³
• Vapor Pressure: 0.11mmHg at 25°C
• Refractive Index: 1.544
• PKA: 9.73±0.29(Predicted)
• CAS DataBase Reference: 1-phenyl-1-aminomethylethene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenyl-1-aminomethylethene(28144-67-4)
• EPA Substance Registry System: 1-phenyl-1-aminomethylethene(28144-67-4)

Safety Data

• Hazardous Substances Data: 28144-67-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 678, 1987 DOI: 10.1021/jo00380a036

InChI:InChI=1/C9H11N/c1-2-9(10)8-6-4-3-5-7-8/h2-7,9H,1,10H2

Upstream product

• 115051-47-3 2-hydroxy-2-phenyl-propionaldehyde-oxime 
• 108-86-1 bromobenzene 
• 106191-56-4 1-(2-chloro-3-propenyl)-2,2,5,5-tetramethyl-2,5-disilazole 
• 119723-67-0 C₁₈H₂₃NO₃S₂Si 
• 98-86-2 acetophenone 
• 100-58-3 phenylmagnesium bromide 
• 128318-85-4 1-(1-azidoprop-2-en-2-yl)benzene 
• 98-83-9 isopropenylbenzene 
• 256950-59-1 N-[2-(phenyl)prop-2-en-1-yl]-N-tert-butoxycarbonyl amide 
• 85278-15-5 N-Methoxycarbonyl-2-phenylallylamine 
• 119723-66-9 C₁₅H₁₅NO₃S₂ 
• 148297-87-4 2,2,2-trichloro-acetimidic acid 2-phenyl-allyl ester 
• 6006-81-1 3-hydroxy-2-phenylpropene 
• 824950-51-8 tert-butyl hydroxy(2-phenylallyl)carbamate 

Downstream Products

• 109045-76-3 (2-phenylprop-1-en-3-yl)trimethylammonium iodide 
• 1428154-23-7 tert-butyl 2-phenylylallyl[(5-oxo-2,5-dihydrofuran-3-yl)methyl]carbamate 
• 1428154-28-2 4-[(2-phenylallylamino)methyl]furan-2(5H)-one 
• 1447974-69-7 5-(chloromethyl)-5-phenyloxazolidin-2-one 
• 1447974-60-8 5-(chloromethyl)-5-phenyloxazolidin-2-one 
• 56865-69-1 N-allyl-2-phenylprop-2-en-1-amine 

Relevant articles and documents

The cascade coupling/iodoaminocyclization reaction of trifluoroacetimidoyl chlorides and allylamines: metal-free access to 2-trifluoromethyl-imidazolines

A metal-free cascade coupling/iodoaminocyclization reaction for the rapid assembly of 2-trifluoromethyl-imidazolines has been disclosed. The transformation applies readily accessible trifluoroacetimidoyl chlorides, allylamines andN-iodosuccinimides as the starting substrates, achieving an efficient and straightforward pathway to construct diverse imidazoline derivatives. Excellent efficiency of the reaction is observed (higher than 90% isolated yield for half of the examples), and the obtained imidazoline products bearing a pendent iodomethyl group could be easily transformed into other synthetically valuable compounds.

Nucleophilic Alkoxylations of Unactivated Alkyl Olefins and α-Methyl Styrene by Photoredox Catalysis

N,N-diisobutylaminophenyl-phenothiazine is a strongly reducing catalyst that allows – for the first time – the photoredox catalytic addition of alcohols to alkyl olefins as non-activated substrates to products with Markovnikov orientation. The irradiation at 365 nm does not require any additional reagent. Using α-methyl styrene as activated substrate we additionally show that this photoredox catalytic method tolerates other functional groups, including allyl, alkynyl, cyanide, and even acid-labile Boc groups within the substrate scope.

Catalytic Geminal Difluorination of Styrenes for the Construction of Fluorine-rich Bioisosteres

A geminal difluorination of alkenes based on I(I)/I(III) catalysis is disclosed, which is compatible with a range of electronically and substitutionally diverse styrenes (27 examples, up to 89% yield). Employing inexpensive p-TolI as the organocatalyst, turnover is enabled by Selectfluor-mediated oxidation to generate the ArIF2 species in situ. Extension to include α-substituted styrenes bearing fluorine-containing groups is disclosed and provides an expansive platform for the generation of fluorine-rich architectures.