129540-21-2

Basic information

• Product Name: 2-(2-Chlorophenyl)pyrrolidine
• Synonyms: 2-(2-CHLOROPHENYL)PYRROLIDINE;pyrrolidine, 2-(2-chlorophenyl)-;1-benzylazetidin-3-yl Methanesulfonate
• CAS NO: 129540-21-2
• Molecular Formula: C₁₀H₁₂ClN
• Molecular Weight: 181.66
• Mol File: 129540-21-2.mol

Chemical Properties

• Boiling Point: 254.1 °C at 760 mmHg
• Flash Point: 107.5 °C
• Appearance: white to beige crystals or crystalline powder
• Density: 1.129 g/cm³
• Vapor Pressure: 0.0176mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: 2-8°C(protect from light)
• PKA: 9.45±0.10(Predicted)
• CAS DataBase Reference: 2-(2-Chlorophenyl)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Chlorophenyl)pyrrolidine(129540-21-2)
• EPA Substance Registry System: 2-(2-Chlorophenyl)pyrrolidine(129540-21-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 129540-21-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(2-Chlorophenyl)pyrrolidine is utilized as an intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for the creation of a wide range of molecules with different functional groups, making it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(2-Chlorophenyl)pyrrolidine is employed as a key component in the development of new drugs. Its structural features enable the design of molecules with specific biological activities, potentially leading to the discovery of novel therapeutic agents. 2-(2-Chlorophenyl)pyrrolidine's ability to interact with various biological targets makes it a promising candidate for the treatment of a range of diseases and disorders.
Used in Psychopharmacology:
2-(2-Chlorophenyl)pyrrolidine may exhibit pharmacological activities that make it a potential candidate for use as a psychoactive drug. Its interaction with the central nervous system could lead to the modulation of neurotransmitter levels, potentially resulting in the treatment of mental health conditions such as anxiety, depression, or other mood disorders. However, further research is required to fully understand its mechanism of action and therapeutic potential.
Safety Considerations:
Due to the potential hazards associated with the use of 2-(2-Chlorophenyl)pyrrolidine, it is crucial to handle this chemical with caution and adhere to proper safety protocols. This includes the use of appropriate personal protective equipment, working in well-ventilated areas, and following established guidelines for the safe handling and disposal of chemicals. By taking these precautions, the risks associated with the use of 2-(2-Chlorophenyl)pyrrolidine can be minimized, allowing for its safe and effective application in various industries.

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

Upstream product

• 129540-25-6 2-(2-chlorophenyl)-1-pyrroline 
• 88-12-0 1-ethenyl-2-pyrrolidinone 
• 7335-25-3 ethyl 2-chlorobenzoate 

Downstream Products

• 129540-28-9 1-[2-(2-Chloro-phenyl)-pyrrolidin-1-yl]-2-hydroxy-2-(4-methylsulfanyl-phenyl)-ethanone 
• 129540-02-9 trans-10-chloro-1,2,3,5,6,10b-hexahydro-6-<4-(methylthio)phenyl>pyrrolo<2,1-a>isoquinoline 
• 129540-02-9 cis-10-chloro-1,2,3,5,6,10b-hexahydro-6-<4-(methylthio)phenyl>pyrrolo<2,1-a>isoquinoline 
• 823190-03-0 2-(2-chloro-phenyl)-pyrrolidine-1-carboxylic acid-tert-butyl ester 
• 1210859-14-5 2-(2-chloro-phenyl)-1-nitroso-pyrrolidine 

Relevant articles and documents

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. 3. A focus on serotonin

A collection of hexahydropyrroloisoquinoline derivatives (1-22), which represent a class of compounds that inhibit the neuronal uptake of dopamine (DA), norepinephrine (NE), and serotonin (5-HT), was investigated in vivo for serotonin-potentiating propert

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.