65476-99-5

Basic information

• Product Name: Benzenebutanamine, -bta--methyl-
• Synonyms: Benzenebutanamine, -bta--methyl-
• CAS NO: 65476-99-5
• Molecular Formula: C₁₁H₁₇N
• Molecular Weight: 163.25938
• Mol File: 65476-99-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzenebutanamine, -bta--methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenebutanamine, -bta--methyl-(65476-99-5)
• EPA Substance Registry System: Benzenebutanamine, -bta--methyl-(65476-99-5)

Safety Data

• Hazardous Substances Data: 65476-99-5(Hazardous Substances Data)

Upstream product

• 117341-61-4 6-Methoxy-5-methyl-3-phenyl-6H-1,2-oxazine 
• 768-56-9 4-Phenylbut-1-ene 
• 61012-64-4 1-tert-butyl-N,1,1-trimethylsilanamine 
• 103-63-9 1-phenyl-2-bromoethane 
• 73475-33-9 2-methyl-4-phenylbutanenitrile 
• 117341-58-9 5,6-Dihydro-6-methoxy-5-methylene-3-phenyl-4H-1,2-oxazine 
• 109925-94-2 5-Methyl-3-phenyl-6-trimethylsilanyloxy-5,6-dihydro-4H-[1,2]oxazine 

Relevant articles and documents

Fast Titanium-Catalyzed Hydroaminomethylation of Alkenes and the Formal Conversion of Methylamine

The scientific interest in catalytic hydroaminoalkylation reactions of alkenes has vastly increased over the past decade, but these reactions have struggled to become a viable option for general laboratory or industrial use because of reaction times of several days. The titanium-based catalytic system introduced in this work not only reduces the reaction time by several orders of magnitude, into the range of minutes, but the catalyst is also demonstrated to be easily available from common starting materials, at a cost of approximately 1 € per millimole of catalyst. We were also able to formally perform C?H activation of methylamine and achieve coupling to a broad variety of alkenes, through silyl protection of the amine and simple deprotection by water.

An Iodine-Catalyzed Hofmann-L?ffler Reaction

Iodine reagents have been identified as economically and ecologically benign alternatives to transition metals, although their application as molecular catalysts in challenging C-H oxidation reactions has remained elusive. An attractive iodine oxidation catalysis is now shown to promote the convenient conversion of carbon-hydrogen bonds into carbon-nitrogen bonds with unprecedented complete selectivity. The reaction proceeds by two interlocked catalytic cycles comprising a radical chain reaction, which is initiated by visible light as energy source. This unorthodox synthetic strategy for the direct oxidative amination of alkyl groups has no biosynthetic precedence and provides an efficient and straightforward access to a general class of saturated nitrogenated heterocycles.

Model Studies of the Reduction of 3-Phenyl-6H-1,2-oxazines, Chemo- and Stereoselectivity: Synthesis of Amino Alcohols, Amino Acids, and Related Compounds

While palladium-catalyzed hydrogenation of 3-phenyl-6H-1,2-oxazine 1 produces primary amine 5 in a nitrogen-transposition reaction, the reductions of the related 1,2-oxazines 2, 10, and the 1,2-oxazin-6-one 3 afford the expected amino alcohols 4, 11, and the γ-amino acid 6, respectively, with low diastereoselectivities.In the presence of acetic acid 3 is reductively converted into γ-keto carboxylic acid 9 and 1 into the γ-lactam derivative 12 probably by a ring contraction to a nitrone intermediate.Raney nickel as the catalyst is able to transform 1,2-oxazine 7 bearing an exo-methylene unit into 3,4-dihydro-2H-pyrrole 13.The reaction of 6H-1,2-oxazine 1 with aluminium amalgam produces pyrrole 14 in moderate yield.Treatment of 1 with sodium in 2-propanol brings about its transformation into pyrrolidine derivative 15 together with pyrrole 14 and amino alcohol 4 as minor products.The chemoselectivity and stereoselectivity of these reductions are discussed including mechanistic proposals for the multistep processes involved. Key Words: 1,2-Oxazines / Hydrogenation, catalytic / Amino alcohols / γ-Amino acids / Pyrroles / γ-Lactams