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

• 1333-74-0 hydrogen 
• 208118-80-3 1-(4-chlorophenyl)ethenylacetamide 
• 1167414-87-0 C₈H₁₀ClN*ClH 
• 108-24-7 acetic anhydride 
• 108-05-4 vinyl acetate 
• 35588-60-4 p-chloro-(R,S)-1-phenylethylamine 
• 141-78-6 ethyl acetate 
• 108-22-5 Isopropenyl acetate 
• 1121583-62-7 isopropyl 2-propoxyacetate 
• 4187-56-8 (S)-1-(p-chlorophenyl)ethylamine 
• 1420472-32-7 (E)-1-(4-chlorophenyl)ethanone O-acetyl oxime 
• 1956-39-4 (E)-1-(4-chlorophenyl)ethanone oxime 
• 937371-83-0 (E)-1-(4-chlorophenyl)ethanone O-benzyl oxime 
• 75-36-5 acetyl chloride 

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.

Diaza-Crown Ether-Bridged Chiral Diphosphoramidite Ligands: Synthesis and Applications in Asymmetric Catalysis

A small library of diaza-crown ether-bridged chiral diphosphoramidite ligands was prepared. In the rhodium-catalyzed asymmetric hydrogenation and hydroformylation reactions, these ligands exhibited distinct properties in catalytic activity and/or enantioselectivity. Hydrogenated products with opposite absolute configurations could be obtained in high yields with excellent ee values by utilizing (S,S)-L1 and (S,S)-L3, respectively. Meanwhile, the addition of alkali metal cations caused variations in catalytic outcomes, showing the supramolecular tunability of these Rh/diphosphoramidite catalytic systems.

The enzymatic resolution of 1-(4-chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide

The kinetic resolution of (R,S)-1-(4-chlorophenyl)ethylamine was accomplished using a commercial lipase from Candida antarctica (Novozym 435). The performance of this lipase was investigated for the enantioselective amidation of (R,S)-1-(4-chlorophenyl)ethylamine, leaving the target product (S)-1-(4-chlorophenyl)ethylamine in its unreacted form. The effects of various types of solvents and an acyl donor, the molar ratio of the substrate to the acyl donor, and the reaction temperature were studied. The optimum reaction conditions were found to result in amidation with methyl 2-tetrahydrofuroate at 40°C in methyl tert-butyl ether, with a substrate/acyl donor molar ratio of 1:2.4. The conversion rate of (R,S)-1-(4-chlorophenyl)ethylamine was 52%, with an enantiomeric excess of 99% towards the unreacted substrate in a reaction time of 22?hours. Finally, using optically pure (S)-1-(4-chlorophenyl)ethylamine as the raw material, the chemical synthesis of (S)-N-(1-(4-chlorphenyl)ethyl)-2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)acetamide, a novel triazolopyrimidine herbicide, was achieved, and the total yield and purity were 83.5% and 95.3%, respectively.