32704-23-7

Basic information

• Product Name: Benzenamine, 4-(2-propenyl)-
• Synonyms: p-Allylanilin;4-allyl-phenylamine;4-allyl-aniline;4-Allyl-anilin
• CAS NO: 32704-23-7
• Molecular Formula: C9H11N
• Molecular Weight: 133.193
• Mol File: 32704-23-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 98-102 °C(Press: 15 Torr)
• Density: 0.978±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzenamine, 4-(2-propenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 4-(2-propenyl)-(32704-23-7)
• EPA Substance Registry System: Benzenamine, 4-(2-propenyl)-(32704-23-7)

Safety Data

• Hazardous Substances Data: 32704-23-7(Hazardous Substances Data)

Upstream product

• 53483-17-3 1-allyl-4-nitro-benzene 
• 7439-89-6 iron 
• 24850-33-7 allyltributylstanane 
• 106-47-8 4-chloro-aniline 
• 300-57-2 allylbenzene 
• 540-37-4 p-aminoiodobenzene 
• 762-72-1 allyl-trimethyl-silane 
• 106-40-1 4-bromo-aniline 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 1610026-13-5 (E)-4-(3-azidoprop-1-enyl)aniline 
• 1610026-33-9 (E)-4-(3-(4-phenyl-1H-1,2,3-triazol-1-yl)prop-1-enyl)aniline 
• 501-92-8 4-(prop-2-enyl)phenol 

Relevant articles and documents

Flow Metal-Free Ar-C Bond Formation via Photogenerated Phenyl Cations

A convenient photochemical flow protocol for the formation of aryl-carbon bonds via photogenerated phenyl cations has been developed. A wide range of phenylated products, including biaryls, allylarenes, 2-arylacetals and benzyl γ-lactones, was smoothly synthesized in satisfactory yields under metal-free conditions. The adoption of a flow reactor often allowed us to adopt higher concentrations of substrates and shorter irradiation times compared to those usually employed in batch systems.

Homolytic vs Heterolytic Paths in the Photochemistry of Haloanilines

The photochemistry of 4-haloanilines and 4-halo-N,N-dimethylanilines has been studied in apolar, polar aprotic, and protic solvents. Photophysical and flash photolysis experiments show that the reaction proceeds in any case from the triplet state. It is rather unreactive in apolar media, the highest value being Π = 0.05 for the iodoanilines in cyclohexane. Changing the solvent has little effect for iodoanilines and for the poorly reacting bromo analogue, while it leads to a variation of over 2 orders of magnitude in the quantum yield for the chloro and fluoro derivatives. The triplets have been characterized at the UB3LYP/6-31G(d) level of theory, evidencing a deformation and an elongation (except for C-F) of the C-X bond. Homolytic fragmentation is in every case endothermic, but calculations in acetonitrile solution show that heterolytic cleavage of C-Cl and C-Br is exothermic. Experimentally, the occurrence of heterolytic fragmentation has been monitored through selective trapping of the resulting phenyl cation by allyltrimethylsilane. Heterolytic dechlorination occurs efficiently in polar media (e.g., Π = 0.77 in MeCN), while debromination remains ineffective due to the short lifetime of the triplet. Heterolytic defluorination is efficient only in protic solvents (Π = 0.48 in MeOH), in accord with calculations showing that in the presence of an ancillary molecule of water fragmentation is exothermic due to the formation of the strong H-F bond. The energy profile for both homo- and heterolytic dissociation paths has been mapped along the reaction coordinates in the gas phase and in acetonitrile. The conditions determining the efficiency and mode of dehalogenation have been defined. This is significant for devising synthetic methods via photogenerated phenyl cations and for rationalizing the photodegradation of halogenated aromatic pollutants and the phototoxic effect of some fluorinated drugs.

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