1189152-82-6

Basic information

• Product Name: (S)-2-(4-BROMOPHENYL)PYRROLIDINE
• Synonyms: (S)-2-(4-BROMOPHENYL)PYRROLIDINE;(2S)-2-(4-broMophenyl)pyrrolidine;(2S)-2-(4-BROMOPHENYL)PYRROLIDINE HCl;Pyrrolidine, 2-(4-bromophenyl)-, (2S)-;(S)-2-(4-bromophenyl)pyrrolidine hydrochloride
• CAS NO: 1189152-82-6
• Molecular Formula: C₁₀H₁₂BrN
• Molecular Weight: 226.11
• Mol File: 1189152-82-6.mol

Chemical Properties

• Boiling Point: 287℃
• Flash Point: 128℃
• Appearance: /
• Density: 1.369
• Storage Temp.: 2-8°C(protect from light)
• PKA: 9.58±0.10(Predicted)
• CAS DataBase Reference: (S)-2-(4-BROMOPHENYL)PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(4-BROMOPHENYL)PYRROLIDINE(1189152-82-6)
• EPA Substance Registry System: (S)-2-(4-BROMOPHENYL)PYRROLIDINE(1189152-82-6)

Safety Data

• Hazardous Substances Data: 1189152-82-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-(4-BROMOPHENYL)PYRROLIDINE is used as a building block for the synthesis of pharmaceutical compounds due to its unique structure and properties. The 4-bromophenyl group can be utilized to create derivatives with specific biological activities, making it a valuable component in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical industry, (S)-2-(4-BROMOPHENYL)PYRROLIDINE is used as a precursor for the synthesis of agrochemicals with potential pesticidal or herbicidal properties. (S)-2-(4-BROMOPHENYL)PYRROLIDINE's unique structure allows for the development of new agrochemicals with improved efficacy and selectivity.
Used in Materials Science:
(S)-2-(4-BROMOPHENYL)PYRROLIDINE is used as a component in the development of new materials with specific properties in materials science. (S)-2-(4-BROMOPHENYL)PYRROLIDINE's unique structure and the 4-bromophenyl group can contribute to the creation of materials with tailored characteristics, such as improved stability, conductivity, or other desired properties.
Overall, (S)-2-(4-BROMOPHENYL)PYRROLIDINE is a versatile chemical compound with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science, due to its unique structure, properties, and stereochemistry.

Upstream product

• 1207729-67-6 (S)-1-((S)-2-methyl-propane-2-sulfinyl)-2-(4-bromophenyl)-pyrrolidine 

Relevant articles and documents

PROCESS FOR SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND PIPERADINES

The present invention provides a highly efficient, versatile one-step process for asymmetric synthesis of either diastereomer of 2-substituted pyrrolidines from a single starting material with excellent yields and high diastereoselectivety. Also provided is a method for the asymmetric synthesis of both diastereomers of 2-substituted piperidines with good yields and excellent diastereoselectivety. Diasteroselectivity is controlled effectively by choice of reducing agent.

A facile asymmetric synthesis of either enantiomer of 2-substituted pyrrolidines

Chemical Reaction Reprentation A new and general method for asymmetric synthesis of either enantiomer of 2-substituted pyrrolidines from a single starting material is described. Reductive cyclization of (Ss)-γ-chloro-N- tertbutanesulfinyl ketimines with LiBHEt3 in THF at -78 to 23 °C afforded (Ss,R)-N-tert-buta.nemnnyl-2-substituted pyrrolidines in excellent yields (88-98%) and with high diastereoselectivity (99:1). The diastereoselectivity is controlled effectively by the choice of reducing agent. Thus, the corresponding epimers of (3 to DIBAL-H/LiHMDS. Deprotection of N-fe/ f-butanesulfinyl-2-substituted pyrrolidines using 4 N HCl in dioxane and MeOH gave the corresponding enantiomers of 2-substituted pyrrolidines in quantative yield. This method was found to be effective for a variety of substrates including aromatic, heteroaromatic, and aliphatic substituents. Extension of this methodology to the formation of 2-substituted piperidines is also illustrated. Reductive cyclization of (5s)-3 in THF at -78 to 23 °C or DIBAL-H/LiHMDS in toluene at -78 to 0 °C afforded the (Ss,R?)-N-tert-butanesulfinyl-2-substituted piperidines in excellent yield (98%) and with high diastereoselectivity (99:1) or (Ss,S)-.N-tert-butanesulfmyl- 2substituted piperidines in good yield (98%) and with high diastereoselectivity (1:99), respectively.

Asymmetric synthesis of 2-substituted pyrrolidines by addition of Grignard reagents to γ-chlorinated N-tert-butanesulfinyl imine

A highly diastereoselective addition of various Grignard reagents to chiral γ-chlorinated N-tert-butanesulfinyl imine resulting in the formation of 2-substituted pyrrolidines is reported. This method is general and also efficient for the preparation of both enantiomers of 2-aryl, 2-alkyl and 2-vinyl substituted pyrrolidines in high yields.