127852-23-7

Basic information

• Product Name: (R)-α-(o-chlorophenyl)ethylamine
• CAS NO: 127852-23-7
• Molecular Weight: 155.627
• Mol File: 127852-23-7.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: (R)-α-(o-chlorophenyl)ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-α-(o-chlorophenyl)ethylamine(127852-23-7)
• EPA Substance Registry System: (R)-α-(o-chlorophenyl)ethylamine(127852-23-7)

Safety Data

• Hazardous Substances Data: 127852-23-7(Hazardous Substances Data)

Upstream product

• 13524-04-4 2'-chloro-sec-phenethyl alcohol 
• 1239016-36-4 (R)-2-(2-chlorophenyl)propanoic acid 
• 2856-63-5 2-Chlorophenylacetonitrile 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 87227-77-8 bishydrochloride salt of cis-1,4-diamino-but-2-ene 
• 1149756-73-9 2-methylpropane-2-sulfinic acid [1-(2-chlorophenyl)ethylidene]amide 
• 39959-67-6 1-(2-Chloro-phenyl)-ethylamine 
• 83834-86-0 N-[1-(2-chloro-phenyl)-ethyl]-formamide 

Downstream Products

• 68285-26-7 (S)-α-(o-chlorophenyl)ethylamine 
• 39959-67-6 (R)-α-(o-chlorophenyl)ethylamine 
• 1637437-40-1 C₂₁H₁₉ClN₄O 
• 127733-51-1 2-{[(E)-(R)-1-(2-Chloro-phenyl)-ethylimino]-methyl}-phenol 
• 1131737-05-7 1-(2,6-dichlorophenyl)ethan-1-amine 

Relevant articles and documents

N-Alkylation of Aqueous Ammonia with Alcohols Leading to Primary Amines Catalyzed by Water-Soluble N-Heterocyclic Carbene Complexes of Iridium

A new catalytic system for the N-monoalkylation of aqueous ammonia with a variety of alcohols was developed. Water-soluble dicationic complexes of iridium bearing N-heterocyclic carbene and diammine ligands exhibited high catalytic activity for this type of reaction on the basis of hydrogen-transfer processes without generating harmful or wasteful byproducts. Various primary amines were efficiently synthesized by using safe, inexpensive, and easily handled aqueous ammonia as a nitrogen source. For example, the reaction of 1-(4-methylphenyl)ethanol with aqueous ammonia in the presence of a water-soluble N-heterocyclic carbene complex of iridium at 150 °C for 40 h gave 1-(4-methylphenyl)ethylamine in 83 % yield.

One-Pot C-H Arylation/Lactamization Cascade Reaction of Free Benzylamines

An efficient method has been developed for the synthesis of seven-membered biaryl lactams involving Pd-catalyzed, native amine-directed, ortho-arylation of benzylamines followed by in situ lactamization. This cascade sequence is enabled by the use of 2-iodobenzoates, which facilitates C-H arylation from the free amine under conditions that typically require an improved directing group approach. This reaction is characterized by a broad substrate scope with good functional group tolerance. The need for an ester versus carboxylic acid-functionalized coupling partner is also explored, as is the potential for synthesizing eight-membered biaryl lactams. Various applications are also investigated, including access to the aza-brassinolide core.

Carbon Dioxide-Mediated C(sp2)-H Arylation of Primary and Secondary Benzylamines

C-C bond formation by transition metal-catalyzed C-H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of ortho-arylbenzylamines, however, effective ortho-C-C bond formation of free primary and secondary benzylamines using PdII remains an outstanding challenge. Presented herein is a new strategy for constructing ortho-arylated primary and secondary benzylamines mediated by carbon dioxide (CO2). The use of CO2 with Pd is critical to allowing this transformation to proceed under relatively mild conditions, and mechanistic studies indicate that it (CO2) is directly involved in the rate-determining step. Furthermore, the milder temperatures furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, an interesting chelate effect is shown to facilitate selective monoarylation.