774-91-4

Basic information

• Product Name: Pyrrolidine, 2-methyl-1-(phenylmethyl)-
• CAS NO: 774-91-4
• Molecular Formula: C12H17N
• Molecular Weight: 175.274
• Mol File: 774-91-4.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: Pyrrolidine, 2-methyl-1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolidine, 2-methyl-1-(phenylmethyl)-(774-91-4)
• EPA Substance Registry System: Pyrrolidine, 2-methyl-1-(phenylmethyl)-(774-91-4)

Safety Data

• Hazardous Substances Data: 774-91-4(Hazardous Substances Data)

Usage

General Description

2-methyl-1-(phenylmethyl) pyrrolidine is an organic compound with the molecular formula C13H171N. It is a colorless to pale yellow liquid with a faint amine odor. This chemical is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals due to its versatile reactivity. It can also be utilized as a chiral auxiliary in asymmetric synthesis to create enantiomerically pure compounds. Additionally, 2-methyl-1-(phenylmethyl) pyrrolidine has potential applications in the development of novel materials for electronic devices and as a solvent in some chemical processes. However, it is important to handle this chemical with care as it can be harmful if ingested, inhaled, or absorbed through the skin, and proper safety measures should be taken when working with it.

Upstream product

• 54436-58-7 N-benzylpent-4-en-1-amine 
• 174500-52-8 (R)-1-(trityloxy)pentan-4-yl acetate 
• 56718-04-8 (4R)-pentane-1,4-diol 
• 626-95-9 1,4-Pentanediol 
• 100-46-9 benzylamine 
• 174500-72-2 Methanesulfonic acid (R)-4-methanesulfonyloxy-1-methyl-butyl ester 
• 123-76-2 levulinic acid 
• 1430962-71-2 N-benzyl-N-(pent-4-en-1-yl)-1H-imidazole-1-carboxamide 
• 1430962-42-7 acetophenone N,N-(benzyl(pent-4-en-1-yl)carbamoyl) oxime 
• 56519-58-5 1-benzyl-2-methyl-1-pyrrolinium perchlorate 
• 1119-51-3 bromopentene 
• 100-44-7 benzyl chloride 
• 765-38-8 2-methyl-1-pyrrolidine 
• 74500-56-4 1,4-pentanediol monotrityl ether 

Downstream Products

• 56519-58-5 1-benzyl-2-methyl-1-pyrrolinium perchlorate 
• 765-38-8 (S)-2-methylpyrrolidine 
• 116614-85-8 ethyl (E)-2-(1-benzylpyrrolidin-2-ylidene)acetate 

Relevant articles and documents

Design, scope and mechanism of highly active and selective chiral NHC-iridium catalysts for the intramolecular hydroamination of a variety of unactivated aminoalkenes

Chiral, cationic NHC-iridium complexes are introduced as catalysts for the intramolecular hydroamination reaction of unactivated aminoalkenes. The catalysts show high activity in the construction of a range of 5- and 6-membered N-heterocycles, which are accessed in excellent optical purity, with various functional groups being tolerated with this system. A major deactivation pathway is presented and eliminated by using alternative reaction conditions. A detailed experimental and computational study on the reaction mechanism is performed providing valuable insights into the mode of action of the catalytic system and pointing to future modifications to be made for this catalytic platform.

On the Superior Activity of In(I) versus In(III) Cations Toward ortho-C-Alkylation of Anilines and Intramolecular Hydroamination of Alkenes

An efficient ortho-C-alkylation of unprotected anilines with a variety of styrenes and alkenes using a univalent cationic indium(I) catalyst is reported. Mechanistic studies revealed that the reaction likely proceeds via a tandem hydroamination/Hofmann-Martius rearrangement. The high compatibility between the cationic indium(I) complex and primary anilines led us to develop an In(I)+-catalyzed hydroamination of alkenes using unprotected primary and secondary alkenylamines. Computations support the catalytic activity of naked In(I)+ ions, with an outer sphere mechanism for the C-N bond formation and a potentially inner sphere protodemetallation.

Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines

The intermolecular hydroamination of unactivated alkenes with simple dialkyl amines remains an unsolved problem in organic synthesis. We report a catalytic protocol for efficient additions of cyclic and acyclic secondary alkyl amines to a wide range of alkyl olefins with complete anti-Markovnikov regioselectivity. In this process, carbon-nitrogen bond formation proceeds through a key aminium radical cation intermediate that is generated via electron transfer between an excited-state iridium photocatalyst and an amine substrate. These reactions are redox-neutral and completely atom-economical, exhibit broad functional group tolerance, and occur readily at room temperature under visible light irradiation. Certain tertiary amine products generated through this method are formally endergonic relative to their constituent olefin and amine starting materials and thus are not accessible via direct coupling with conventional ground-state catalysts.