186296-21-9

Basic information

• Product Name: (R)-(+)-p-chloro-N-acetyl-1-methylbenzylamine
• Synonyms: (R)-(+)-p-chloro-N-acetyl-1-methylbenzylamine;(R)-N-[1-(4-Chlorophenyl)ethyl]acetamide
• CAS NO: 186296-21-9
• Molecular Formula: C10H12ClNO
• Molecular Weight: 197.66
• Mol File: 186296-21-9.mol
• Article Data: 72

Chemical Properties

• Appearance: /
• Density: 1.136
• CAS DataBase Reference: (R)-(+)-p-chloro-N-acetyl-1-methylbenzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-p-chloro-N-acetyl-1-methylbenzylamine(186296-21-9)
• EPA Substance Registry System: (R)-(+)-p-chloro-N-acetyl-1-methylbenzylamine(186296-21-9)

Safety Data

• Hazardous Substances Data: 186296-21-9(Hazardous Substances Data)

Usage

General Description

(R)-(+)-p-chloro-N-acetyl-1-methylbenzylamine, also known as PCAMB, is a chemical compound with a molecular formula of C10H12ClNO. It is a chiral amine with a chlorine atom and an acetyl group attached to a methylbenzylamine molecule. (R)-(+)-p-chloro-N-acetyl-1-methylbenzylamine is often used as a reagent in chemical synthesis, particularly in the production of chiral pharmaceuticals and agrochemicals. PCAMB is also used as a building block in organic chemistry, where its chirality can influence the stereochemical outcome of reactions. Its unique structure and properties make it a valuable tool in synthetic chemistry for creating complex and diverse molecules.

Upstream product

• 208118-80-3 1-(4-chlorophenyl)ethenylacetamide 
• 937371-83-0 (E)-1-(4-chlorophenyl)ethanone O-benzyl oxime 
• 108-24-7 acetic anhydride 
• 1956-39-4 (E)-1-(4-chlorophenyl)ethanone oxime 
• 29540-84-9 4-chlorophenyl trifluoromethanesulfonate 
• 106-48-9 4-chloro-phenol 
• 1956-39-4 4-chloroacetophenone oxime 
• 99-91-2 para-chloroacetophenone 
• 27298-99-3 (R)-1-(4-chlorophenyl)ethylamine 
• 75-36-5 acetyl chloride 
• 35588-60-4 p-chloro-(R,S)-1-phenylethylamine 
• 1420472-32-7 (E)-1-(4-chlorophenyl)ethanone O-acetyl oxime 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 71426-50-1 Syn-α-Brom-p-chlor-acetophenon oxim 

Relevant articles and documents

Monophosphite ligands derived from carbohydrates and H8-BINOL: Highly enantioselective Rh-catalyzed asymmetric hydrogenations

A series of monophosphite ligands derived from carbohydrates and H 8-BINOL have been synthesized. Excellent enantioselectivities (over 99% ee) were obtained when these ligands were applied in the Rh-catalyzed asymmetric hydrogenation of dimethy

Asymmetric enamide hydrogenation using planar-chiral cyrhetrenes

The catalytic asymmetric hydrogenation of α-arylenamides using catalysts prepared in situ from [Rh(cod)2]BF4 and cyrhetrenyldiphosphines was effective with a range of enamides. The corresponding acetamides were obtained with up to 93

Biocatalytic, Intermolecular C?H Bond Functionalization for the Synthesis of Enantioenriched Amides

Directed evolution of heme proteins has opened access to new-to-nature enzymatic activity that can be harnessed to tackle synthetic challenges. Among these, reactions resulting from active site iron-nitrenoid intermediates present a powerful strategy to forge C?N bonds with high site- and stereoselectivity. Here we report a biocatalytic, intermolecular benzylic C?H amidation reaction operating at mild and scalable conditions. With hydroxamate esters as nitrene precursors, feedstock aromatic compounds can be converted to chiral amides with excellent enantioselectivity (up to >99 % ee) and high yields (up to 87 %). Kinetic and computational analysis of the enzymatic reaction reveals rate-determining nitrenoid formation followed by stepwise hydrogen atom transfer-mediated C?H functionalization.

New chiral ferrocene/indole-based diphosphine ligands for Rh-catalyzed asymmetric hydrogenation of functionalized olefins

Convenient synthesis of a new family of chiral ferrocene/indole-based diphosphine ligands, (Rc,Rp)-IndoFerroPhos (L), from (Sc,Rp)-PPFA and 2-(diphenylphosphino)indole has been described. These new ligands exhibited high efficiency in the Rh-catalyzed asymmetric hydrogenation of functionalized olefins including α-dehydroamino acid esters, α-enamides and dimethyl itaconate, in which up to >99% yield and 98% ee were achieved.

Asymmetric Synthesis of Chiral Primary Amines by Ruthenium-Catalyzed Direct Reductive Amination of Alkyl Aryl Ketones with Ammonium Salts and Molecular H2

A ruthenium/C3-TunePhos catalytic system has been identified for highly efficient direct reductive amination of simple ketones. The strategy makes use of ammonium acetate as the amine source and H2 as the reductant and is a user-friendly and operatively simple access to industrially relevant primary amines. Excellent enantiocontrol (>90% ee for most cases) was achieved with a wide range of alkyl aryl ketones. The practicability of this methodology has been highlighted by scalable synthesis of key intermediates of three drug molecules. Moreover, an improved synthetic route to the optimal diphosphine ligand C3-TunePhos is also presented.