298690-74-1

Basic information

• Product Name: 3-(2-CHLORO-PHENYL)-PYRROLIDINE
• Synonyms: 2-(3-CHLOROPHENYL)PYRROLIDINE;AKOS BB-8867;CHEMBRDG-BB 4006410;Pyrrolidine, 2-(3-chlorophenyl)-
• CAS NO: 298690-74-1
• Molecular Formula: C₁₀H₁₂ClN
• Molecular Weight: 181.66
• Mol File: 298690-74-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 260.1 °C at 760 mmHg
• Flash Point: 111.1 °C
• Appearance: /
• Density: 1.129 g/cm³
• Vapor Pressure: 0.00763mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: 2-8°C(protect from light)
• PKA: 9.58±0.10(Predicted)
• CAS DataBase Reference: 3-(2-CHLORO-PHENYL)-PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-CHLORO-PHENYL)-PYRROLIDINE(298690-74-1)
• EPA Substance Registry System: 3-(2-CHLORO-PHENYL)-PYRROLIDINE(298690-74-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 298690-74-1(Hazardous Substances Data)

Usage

General Description

3-(2-chloro-phenyl)-pyrrolidine is a chemical compound with the molecular formula C10H12ClN. It is a pyrrolidine derivative with a chlorine atom attached to the 2-position of the phenyl ring. 3-(2-CHLORO-PHENYL)-PYRROLIDINE is used in organic synthesis and pharmaceutical research. It has been investigated for its potential pharmacological properties, including its ability to act as a ligand for various receptors or enzymes in the body. The compound's structure and properties make it a valuable tool for studying the structure-activity relationships of different chemicals and their potential biological effects.

InChI:InChI=1/C10H12ClN/c11-9-4-1-3-8(7-9)10-5-2-6-12-10/h1,3-4,7,10,12H,2,5-6H2

Upstream product

• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 1128-76-3 3-chloro-benzoic acid ethyl ester 
• 535-80-8 3-chlorobenzoate 
• 374588-99-5 5-(3-chlorophenyl)-3,4-dihydro-2H-pyrrole 

Downstream Products

• 1218950-22-1 C₂₀H₂₃ClN₂O₃S 

Relevant articles and documents

Design, synthesis and biological evaluation of N-hydroxy-aminobenzyloxyarylamide analogues as novel selective κ opioid receptor antagonists

Aminobenzyloxyarylamide derivatives 1a-i and 2a-t were designed and synthesized as novel selective κ opioid receptor (KOR) antagonists. The benzoyl amide moiety of LY2456302 was changed into N-hydroxybenzamide and benzisoxazole-3(2H)-one to investigate whether it could increase the binding affinity or selectivity for KOR. All target compounds were evaluated in radioligand binding assays for opioid receptor binding affinity. These efforts led to the identification of compound 1c (κ Ki = 179.9 nM), which exhibited high affinity for KOR. Moreover, the selectivity of KOR over MOR and DOR increased nearly 2-fold and 7-fold, respectively, compared with (±)LY2456302.

Stereocomplementary Synthesis of Pharmaceutically Relevant Chiral 2-Aryl-Substituted Pyrrolidines Using Imine Reductases

Exploring a collection of naturally occurring imine reductases (IREDs) identified two stereocomplementary IREDs with reducing activity toward sterically hindered 2-aryl-substituted pyrrolines. Using (R)-selective ScIR and (S)-selective SvIR, various chiral 2-aryl-substituted pyrrolidines with excellent enantioselectivity (>99% ee) were stereocomplementarily synthesized in good yield (60-80%), demonstrating the feasibility of IREDs for generating pharmaceutically relevant chiral 2-aryl-substituted pyrrolidine intermediates.

Pyrroloisoquinoline antidepressants. 2. In-depth exploration of structure-activity relationships

A series of pyrrolo[2,1-a]isoquinolines, and related compounds, were examined for antidepressant-like activity, by virtue of their antagonism of tetrabenazine-induced ptosis and sedation, and inhibition of biogenic amine uptake. Thus, we have identified some of the most potent antagonists of TBZ-induced ptosis and some of the most potent inhibitors of the uptake of dopamine, norepinephrine, and serotonin (in rat brain synaptosomes) ever reported. Compounds of particular note, in this regard, are 52b, 29b, 22b, and 48b, respectively. Biological activity was chiefly manifested by the trans isomeric class. Also, through resolution of four compounds, 7b, 24b, 37b, and 48b, biological activity was found to be associated with the (+) enantiomer subgroup (salts measured at 589 nm in MeOH), corresponding to the 6S,10bR absolute configuration for 7b, 37b, and 48b, and the 6R,10bR configuration for 24b. An X-ray determination on (+)-24b·HBr established its absolute configuration; configurations for the other compounds were verified by enantiospecific synthesis starting with (+)-(R)-2-phenylpyrrolidine. Regarding the pendant phenyl ring, diverse substitution patterns were investigated. Those substitutions that were particularly unfavorable were 3',4',5'-trimethoxy (20b), 2',3',4',5',6'-pentafluoro (34b), 2'-trifluoromethyl (38b), 3',5'-bis(trifluoromethyl) (42b), 4'-n-butyl (44b), 2'-cyano (47b), 4'-methylsulfonyl (50b), and 2'-carboxy (58b). Exceedingly potent compounds, in one way or another, were 10b-12b, 22b, 23b, 25b, 28b, 29b, 33b, 45b, 48b, 51b-53b. The pattern of aromatic substitution had a strong impact on selectivity in the uptake tests (NE vs. DA vs. 5-HT). Activity was significantly diminished by methyl substitution of 7b at the 5 (65, 66), 6 (61b), or 10b (60b) position, by changing the phenyl group of 7b to cyclohexyl (67b), benzyl (68b), or H (72), by moving the phenyl group of 7b to the 5 (69) or 10b (70) position, by expansion of ring B to an azepine (78b), and by modification of ring C to an azetidine (77b), piperidine (75b), or azepine (74b). The interaction of selected analogues with various CNS receptors is reported. Little affinity was shown for the muscarinic cholinergic receptor, suggesting a lack of anticholinergic side effects. Interestingly, 24b and 33b displayed a high affinity for the serotonin-2 receptor, analogous to mianserin and clomipramine. After the body of data was reviewed, derivatives 24b and 48b were chosen for advanced development.