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1-(4-Aminophenyl)pyrrolidin-2-one, also known as 4-AP-2-P, is a chemical compound belonging to the class of pyrrolidinones. It serves as an intermediate molecule in the synthesis of certain pharmaceutical drugs and is recognized for its potential therapeutic properties in medicinal chemistry research, particularly for psychiatric and neurological disorders.

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  • 13691-22-0 Structure
  • Basic information

    1. Product Name: 1-(4-Aminophenyl)pyrrolidin-2-one
    2. Synonyms: 1-(4-Aminophenyl)-2-pyrrolidone;1-(4-aminophenyl)-2-pyrrolidinone(SALTDATA: FREE);1-(4-Aminophenyl)-2-pyrilidinone
    3. CAS NO:13691-22-0
    4. Molecular Formula: C10H12N2O
    5. Molecular Weight: 176.22
    6. EINECS: 275-416-0
    7. Product Categories: N/A
    8. Mol File: 13691-22-0.mol
  • Chemical Properties

    1. Melting Point: 122-123℃
    2. Boiling Point: 462.2 °C at 760 mmHg
    3. Flash Point: 233.3 °C
    4. Appearance: /
    5. Density: 1.234
    6. Vapor Pressure: 1.01E-08mmHg at 25°C
    7. Refractive Index: 1.63
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 5.05±0.10(Predicted)
    11. CAS DataBase Reference: 1-(4-Aminophenyl)pyrrolidin-2-one(CAS DataBase Reference)
    12. NIST Chemistry Reference: 1-(4-Aminophenyl)pyrrolidin-2-one(13691-22-0)
    13. EPA Substance Registry System: 1-(4-Aminophenyl)pyrrolidin-2-one(13691-22-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 13691-22-0(Hazardous Substances Data)

13691-22-0 Usage

Uses

Used in Pharmaceutical Industry:
1-(4-Aminophenyl)pyrrolidin-2-one is used as an intermediate in the synthesis of pharmaceutical drugs for its potential therapeutic properties.
Used in Medicinal Chemistry Research:
1-(4-Aminophenyl)pyrrolidin-2-one is used as a research compound for exploring its potential in treating psychiatric and neurological disorders due to its neuroprotective and analgesic properties.
Used in Drug Development:
1-(4-Aminophenyl)pyrrolidin-2-one is used as a promising candidate for the development of novel drugs and therapies, pending further studies to fully understand its effects and potential applications in various medical fields.

Check Digit Verification of cas no

The CAS Registry Mumber 13691-22-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,6,9 and 1 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 13691-22:
(7*1)+(6*3)+(5*6)+(4*9)+(3*1)+(2*2)+(1*2)=100
100 % 10 = 0
So 13691-22-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H12N2O/c11-8-3-5-9(6-4-8)12-7-1-2-10(12)13/h3-6H,1-2,7,11H2

13691-22-0 Well-known Company Product Price

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  • Aldrich

  • (CBR00182)  1-(4-Aminophenyl)-2-pyrrolidinone  AldrichCPR

  • 13691-22-0

  • CBR00182-1G

  • 2,901.60CNY

  • Detail

13691-22-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(4-Aminophenyl)pyrrolidin-2-one

1.2 Other means of identification

Product number -
Other names 1-(4-Aminophenyl)-2-pyrrolidinone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13691-22-0 SDS

13691-22-0Relevant articles and documents

Characterization of crystal water molecules in a high-affinity inhibitor and hematopoietic prostaglandin D synthase complex by interaction energy studies

Takaya, Daisuke,Inaka, Koji,Omura, Akifumi,Takenuki, Kenji,Kawanishi, Masashi,Yabuki, Yukako,Nakagawa, Yukari,Tsuganezawa, Keiko,Ogawa, Naoko,Watanabe, Chiduru,Honma, Teruki,Aritake, Kosuke,Urade, Yoshihiro,Shirouzu, Mikako,Tanaka, Akiko

, p. 4726 - 4734 (2018)

Hematopoietic prostaglandin D synthase (H-PGDS) is one of the two enzymes that catalyze prostaglandin D2 synthesis and a potential therapeutic target of allergic and inflammatory responses. To reveal key molecular interactions between a high-affinity ligand and H-PGDS, we designed and synthesized a potent new inhibitor (KD: 0.14 nM), determined the crystal structure in complex with human H-PGDS, and quantitatively analyzed the ligand–protein interactions by the fragment molecular orbital calculation method. In the cavity, 10 water molecules were identified, and the interaction energy calculation indicated their stable binding to the surface amino acids in the cavity. Among them, 6 water molecules locating from the deep inner cavity to the peripheral part of the cavity contributed directly to the ligand binding by forming hydrogen bonding interactions. Arg12, Gly13, Gln36, Asp96, Trp104, Lys112 and an essential co-factor glutathione also had strong interactions with the ligand. A strong repulsive interaction between Leu199 and the ligand was canceled out by forming a hydrogen bonding network with the adjacent conserved water molecule. Our quantitative studies including crystal water molecules explained that compounds with an elongated backbone structure to fit from the deep inner cavity to the peripheral part of the cavity would have strong affinity to human H-PGDS.

UREA DERIVATIVE MODULATORS OF TRYPTOPHAN CATABOLISM

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Page/Page column 120-121, (2019/12/25)

There are described compounds of formula (I): (I) and their use as a medicament in the treatment of diseases associated with the abnormal or elevated catabolism of tryptophan, such as, cancer, immunosuppression, viral infection, depression, a neurodegener

Copper-Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amides

De, Subhadip,Yin, Junli,Ma, Dawei

supporting information, p. 4864 - 4867 (2017/09/23)

Cu2O/N,N′-bis(thiophen-2-ylmethyl)oxalamide is established to be an effective catalyst system for Goldberg amidation with inferior reactive (hetero)aryl chlorides, which have not been efficiently documented by Cu-catalysis to date. The reaction is well liberalized toward a variety of functionalized (hetero)aryl chlorides and a wide range of aromatic and aliphatic primary amides in good to excellent yields. Furthermore, the arylation of lactams and oxazolidinones is achieved. The present catalytic system also accomplished an intramolecular cross-coupling product.

Phenyl Esters Are Potent Inhibitors of Caseinolytic Protease P and Reveal a Stereogenic Switch for Deoligomerization

Hackl, Mathias W.,Lakemeyer, Markus,Dahmen, Maria,Glaser, Manuel,Pahl, Axel,Lorenz-Baath, Katrin,Menzel, Thomas,Sievers, Sonja,B?ttcher, Thomas,Antes, Iris,Waldmann, Herbert,Sieber, Stephan A.

supporting information, p. 8475 - 8483 (2015/07/15)

Caseinolytic protease P (ClpP) represents a central bacterial degradation machinery that is involved in cell homeostasis and pathogenicity. The functional role of ClpP has been studied by genetic knockouts and through the use of beta-lactones, which remain the only specific inhibitors of ClpP discovered to date. Beta-lactones have served as chemical tools to manipulate ClpP in several organisms; however, their potency, selectivity and stability is limited. Despite detailed structural insights into the composition and conformational flexibility of the ClpP active site, no rational efforts to design specific non-beta-lactone inhibitors have been reported to date. In this work, an unbiased screen of more than 137000 compounds was used to identify five phenyl ester compounds as highly potent ClpP inhibitors that were selective for bacterial, but not human ClpP. The potency of phenyl esters largely exceeded that of beta-lactones in ClpP peptidase and protease inhibition assays and displayed unique target selectivity in living S. aureus cells. Analytical studies revealed that while phenyl esters are cleaved like native peptide substrates, they remain covalently trapped as acyl-enzyme intermediates in the active site. The synthesis of 36 derivatives and subsequent structure-activity relationship (SAR) studies provided insights into conserved structural elements that are important for inhibition potency and acylation reactivity. Moreover, the stereochemistry of a methyl-substituent at the alpha position to the ester, resembling amino acid side chains in peptide substrates, impacted ClpP complex stability, causing either dissociation into heptamers or retention of the tetradecameric state. Mechanistic insights into this intriguing stereo switch and the phenyl ester binding mode were obtained by molecular docking experiments.

Heterogeneous CuII-catalysed solvent-controlled selective N-arylation of cyclic amides and amines with bromo-iodoarenes

Kundu, Debasish,Bhadra, Sukalyan,Mukherjee, Nirmalya,Sreedhar, Bojja,Ranu, Brindaban C.

, p. 15759 - 15768 (2013/11/19)

A selective N-arylation of cyclic amides and amines in DMF and water, respectively, catalysed by CuII/Al2O3 has been achieved. This protocol has been employed for the synthesis of a library of arenes bearing a cyclic amide and an amine moiety at two ends, including a few scaffolds of therapeutic importance. The mechanism has been established based on detailed electron paramagnetic resonance (EPR) spectroscopy, X-ray photoelectron spectroscopy (XPS), UV diffuse reflectance spectroscopy (DRS) and inductively coupled plasma-mass spectrometry (ICP-MS) studies of the catalyst at different stages of the reaction. The CuII/Al2O 3 catalyst was recovered and recycled for subsequent reactions. One over the other: A selective N-arylation of cyclic amides and amines in DMF and water, respectively, catalyzed by CuII/Al2O3 has been achieved (see scheme). This protocol has been employed for the synthesis of a library of arenes bearing cyclic amide and amine moieties at two ends including a few scaffolds of therapeutic importance. The mechanism has been established based on detailed spectroscopic studies (FG=functional group). Copyright

Highly selective reduction of nitroarenes by iron(0) nanoparticles in water

Dey, Raju,Mukherjee, Nirmalya,Ahammed, Sabir,Ranu, Brindaban C.

supporting information; experimental part, p. 7982 - 7984 (2012/09/08)

Highly selective reduction of nitroarenes has been achieved using iron metal nanoparticles in water at room temperature. A wide spectrum of reducible functionalities remained inert under the reaction conditions. During the reaction a change in shape of Fe nanoparticles was observed.

Hydrogenation of azides over copper nanoparticle surface using ammonium formate in water

Ahammed, Sabir,Saha, Amit,Ranu, Brindaban C.

experimental part, p. 7235 - 7239 (2011/10/18)

Aryl azides undergo clean reduction by copper nanoparticles and ammonium formate in water. The surface hydrogen on copper nanoparticles is considered to be the active reducing species. A variety of functionalized aryl azides and aryl sulfonyl azides are reduced by this procedure to the corresponding amines with excellent chemoselectivity in high yields.

CYSTEINE PROTEASE INHIBITORS

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Page/Page column 56-57, (2009/12/05)

To provide a compound having an excellent cysteine protease inhibitory effect, and to provide a drug for treatment or prevention of the disease selected from the group consisting of osteoporosis, osteoarthritis, chronic rheumatoid arthritis, Paget's disea

Copper-catalyzed C-N coupling of amides and nitrogen-containing heterocycles in the presence of cesium fluoride

Phillips, Dean P.,Zhu, Xue-Feng,Lau, Thomas L.,He, Xiaohui,Yang, Kunyong,Liu, Hong

supporting information; experimental part, p. 7293 - 7296 (2010/03/03)

The copper-catalyzed C-N coupling of amides to aryl halides usually requires the use of strong alkali metal bases, such as K2CO3, K3PO4, and Cs2CO3, at high temperature. We discovered that

PYRAZINE DICARBOXAMIDES AND THE USE THEREOF

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Page/Page column 23, (2010/11/08)

The invention relates to novel pyrazine dicarboxamides, methods for the use thereof, their use for treating and/or preventing diseases as well as to their use for producing medicaments for treating and/or preventing diseases, particularly thromboembolic disorders.

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