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1-(2-Nitrophenyl)piperidine is an organic compound with the molecular formula C11H12N2O2. It is a derivative of piperidine, featuring a nitrophenyl group attached to the first carbon of the piperidine ring. 1-(2-NITROPHENYL)PIPERIDINE is known for its potential applications in the pharmaceutical industry due to its unique chemical structure and properties.

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  • 15822-77-2 Structure
  • Basic information

    1. Product Name: 1-(2-NITROPHENYL)PIPERIDINE
    2. Synonyms: 2-PIPERIDINONITROBENZENE;1-(2-NITROPHENYL)PIPERIDINE;BUTTPARK 96\57-88;1-Piperidino-2-nitrobenzene
    3. CAS NO:15822-77-2
    4. Molecular Formula: C11H14N2O2
    5. Molecular Weight: 206.24
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 15822-77-2.mol
  • Chemical Properties

    1. Melting Point: 77-79
    2. Boiling Point: 337.7 °C at 760 mmHg
    3. Flash Point: 158 °C
    4. Appearance: /
    5. Density: 1.188 g/cm3
    6. Vapor Pressure: 0.000103mmHg at 25°C
    7. Refractive Index: 1.578
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: 1-(2-NITROPHENYL)PIPERIDINE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 1-(2-NITROPHENYL)PIPERIDINE(15822-77-2)
    12. EPA Substance Registry System: 1-(2-NITROPHENYL)PIPERIDINE(15822-77-2)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 20/21/22-36/37/38
    3. Safety Statements: 26-36/37/39-37
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 15822-77-2(Hazardous Substances Data)

15822-77-2 Usage

Uses

1. Used in Pharmaceutical Industry:
1-(2-Nitrophenyl)piperidine is used as a key intermediate in the synthesis of various pharmaceutical compounds, specifically for the development of analgesic drugs. Its unique structure allows for the creation of potent and effective pain-relieving medications.
a) As a precursor for Butylbenzyl Methylsulfonyl Aminophenyl Propanamide TRPV1 Antagonists:
1-(2-Nitrophenyl)piperidine is utilized in the preparation of butylbenzyl methylsulfonyl aminophenyl propanamide TRPV1 antagonists. These antagonists are potential analgesics, targeting the transient receptor potential vanilloid 1 (TRPV1) receptor, which plays a crucial role in pain sensation. By blocking this receptor, these antagonists can effectively alleviate pain.
b) In the Synthesis of (Methylsulfonylamino)benzenes as Vanilloid Antagonists:
1-(2-Nitrophenyl)piperidine is also used to synthesize (methylsulfonylamino)benzenes, which are vanilloid antagonists. These compounds exhibit excellent analgesic activity by targeting the vanilloid receptor, another key player in the pain response. The development of such antagonists can lead to the creation of novel and effective pain-relieving drugs.

Check Digit Verification of cas no

The CAS Registry Mumber 15822-77-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,8,2 and 2 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 15822-77:
(7*1)+(6*5)+(5*8)+(4*2)+(3*2)+(2*7)+(1*7)=112
112 % 10 = 2
So 15822-77-2 is a valid CAS Registry Number.
InChI:InChI=1/C11H14N2O2/c14-13(15)11-7-3-2-6-10(11)12-8-4-1-5-9-12/h2-3,6-7H,1,4-5,8-9H2

15822-77-2 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (B25116)  1-(2-Nitrophenyl)piperidine, 98%   

  • 15822-77-2

  • 5g

  • 630.0CNY

  • Detail
  • Alfa Aesar

  • (B25116)  1-(2-Nitrophenyl)piperidine, 98%   

  • 15822-77-2

  • 25g

  • 2315.0CNY

  • Detail
  • Alfa Aesar

  • (B25116)  1-(2-Nitrophenyl)piperidine, 98%   

  • 15822-77-2

  • 100g

  • 7178.0CNY

  • Detail

15822-77-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(2-NITROPHENYL)PIPERIDINE

1.2 Other means of identification

Product number -
Other names 1-(2-Nitrophenyl)piperidine

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:15822-77-2 SDS

15822-77-2Relevant articles and documents

Synthesis, antifungal activity and QSAR of some novel carboxylic acid amides

Du, Shijie,Lu, Huizhe,Yang, Dongyan,Li, Hong,Gu, Xilin,Wan, Chuan,Jia, Changqing,Wang, Mian,Li, Xiuyun,Qin, Zhaohai

, p. 4071 - 4087 (2015)

A series of novel aromatic carboxylic acid amides were synthesized and tested for their activities against six phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to good activity. Among them N-(2-(1H-indazol-1-yl)phenyl)-2-(trifluoromethyl)benzamide (3c) exhibited the highest antifungal activity against Pythium aphanidermatum (EC50 = 16.75 μg/mL) and Rhizoctonia solani (EC50 = 19.19 μg/mL), compared to the reference compound boscalid with EC50 values of 10.68 and 14.47 μg/mL, respectively. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were employed to develop a three-dimensional quantitative structure-activity relationship model for the activity of the compounds. In the molecular docking, a fluorine atom and the carbonyl oxygen atom of 3c formed hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.

“TPG-lite”: A new, simplified “designer” surfactant for general use in synthesis under micellar catalysis conditions in recyclable water

Thakore, Ruchita R.,Takale, Balaram S.,Hu, Yuting,Ramer, Selene,Kostal, Jakub,Gallou, Fabrice,Lipshutz, Bruce H.

, (2021/04/22)

Using the oxidized, carboxylic acid-containing form of MPEG-750, esterification with racemic vitamin E affords a new surfactant (TPG-lite) that functions as an enabling, nanoreactor-forming amphiphile for use in many types of important reactions in synthesis. The presence of a single ester bond is suggestive of simplified treatment as a component of (eventual) reaction waste water, after recycling. Many types of reactions, including aminations, Suzuki-Miyaura, SNAr, and several others are compared directly with TPGS-750-M, leading to the conclusion that TPG-lite can function as an equivalent nanomicelle-forming surfactant in water. Prima facie evidence amassed via DLS and cryo-TEM analyses support these experimental observations. In silico evaluations of the aquatic toxicity and carcinogenicity of TPG-lite indicate that it is safe to use.

Optimisation of 2-(N-phenyl carboxamide) triazolopyrimidine antimalarials with moderate to slow acting erythrocytic stage activity

Bailey, Brodie L.,Nguyen, William,Ngo, Anna,Goodman, Christopher D.,Gancheva, Maria R.,Favuzza, Paola,Sanz, Laura M.,Gamo, Francisco-Javier,Lowes, Kym N.,McFadden, Geoffrey I.,Wilson, Danny W.,Laleu, Beno?t,Brand, Stephen,Jackson, Paul F.,Cowman, Alan F.,Sleebs, Brad E.

, (2021/08/30)

Malaria is a devastating parasitic disease caused by parasites from the genus Plasmodium. Therapeutic resistance has been reported against all clinically available antimalarials, threatening our ability to control the disease and therefore there is an ongoing need for the development of novel antimalarials. Towards this goal, we identified the 2-(N-phenyl carboxamide) triazolopyrimidine class from a high throughput screen of the Janssen Jumpstarter library against the asexual stages of the P. falciparum parasite. Here we describe the structure activity relationship of the identified class and the optimisation of asexual stage activity while maintaining selectivity against the human HepG2 cell line. The most potent analogues from this study were shown to exhibit equipotent activity against P. falciparum multidrug resistant strains and P. knowlesi asexual parasites. Asexual stage phenotyping studies determined the triazolopyrimidine class arrests parasites at the trophozoite stage, but it is likely these parasites are still metabolically active until the second asexual cycle, and thus have a moderate to slow onset of action. Non-NADPH dependent degradation of the central carboxamide and low aqueous solubility was observed in in vitro ADME profiling. A significant challenge remains to correct these liabilities for further advancement of the 2-(N-phenyl carboxamide) triazolopyrimidine scaffold as a potential moderate to slow acting partner in a curative or prophylactic antimalarial treatment.

Electrochemical Synthesis of Benzo[ d]imidazole via Intramolecular C(sp3)-H Amination

Li, An,Li, Caohui,Li, Lijun,Liu, Yu,Tang, Kewen,Yang, Tao,Yang, Zan,Zhou, Congshan

, (2022/01/03)

An electrochemical dehydrogenative amination for the synthesis of benzimidazoles was developed. This electrosynthesis method could address the limitations of the C(sp3)-H intramolecular amination synthesis reaction and provide novel access to obtain 1,2-disubstituted benzimidazoles without transition metals and oxidants. Under undivided electrolytic conditions, various benzimidazole derivatives could be synthesized, exhibiting functional group tolerance.

Discovery of Selective Inhibitors of Endoplasmic Reticulum Aminopeptidase 1

Maben, Zachary,Arya, Richa,Rane, Digamber,An, W. Frank,Metkar, Shailesh,Hickey, Marc,Bender, Samantha,Ali, Akbar,Nguyen, Tina T.,Evnouchidou, Irini,Schilling, Roger,Stratikos, Efstratios,Golden, Jennifer,Stern, Lawrence J.

, p. 103 - 121 (2020/02/20)

ERAP1 is an endoplasmic reticulum-resident zinc aminopeptidase that plays an important role in the immune system by trimming peptides for loading onto major histocompatibility complex proteins. Here, we report discovery of the first inhibitors selective for ERAP1 over its paralogues ERAP2 and IRAP. Compound 1 (N-(N-(2-(1H-indol-3-yl)ethyl)carbamimidoyl)-2,5-difluorobenzenesulfonamide) and compound 2 (1-(1-(4-acetylpiperazine-1-carbonyl)cyclohexyl)-3-(p-tolyl)urea) are competitive inhibitors of ERAP1 aminopeptidase activity. Compound 3 (4-methoxy-3-(N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)sulfamoyl)benzoic acid) allosterically activates ERAP1's hydrolysis of fluorogenic and chromogenic amino acid substrates but competitively inhibits its activity toward a nonamer peptide representative of physiological substrates. Compounds 2 and 3 inhibit antigen presentation in a cellular assay. Compound 3 displays higher potency for an ERAP1 variant associated with increased risk of autoimmune disease. These inhibitors provide mechanistic insights into the determinants of specificity for ERAP1, ERAP2, and IRAP and offer a new therapeutic approach of specifically inhibiting ERAP1 activity in vivo.

Half-sandwich (η5-Cp?)Rh(iii) complexes of pyrazolated organo-sulfur/selenium/tellurium ligands: Efficient catalysts for base/solvent free C-N coupling of chloroarenes under aerobic conditions

Joshi, Raj Kumar,Sharma, Charu,Sharma, Kamal Nayan,Srivastava, Avinash Kumar

supporting information, p. 3599 - 3606 (2020/06/10)

Three new pyrazolated chalcogenoether ligated Rh(iii) half-sandwich complexes (1-3) were synthesised by the thermal reaction of chalcogenoether (S, Se and Te) substituted 1H-pyrazole ligands (L1-L3) and [(η5-C5Me5)RhCl]2 in methanol. The complexes were fully characterised by various spectroscopic techniques, and the molecular structures of complexes 1 and2 were also established through single crystal X-ray crystallographic analysis, which indicates a pseudo-octahedral half-sandwich piano-stool geometry around the rhodium metal. All three complexes were found to be thermally stable and insensitive towards air and moisture. One mol% of Rh(iii) complexes (1-3) along with 10 mol% of Cu(OAc)2 were explored for the Buchwald-Hartwig type C-N coupling reactions of amine and aryl chloride. Good to excellent yields (89-92%) of the coupling products were obtained with seleno- and thio-ether functionalised pyrazolated Rh(iii) complexes (1 and 2), while an average yield (39%) was obtained with the telluro-ether functionalised complex (3). In contrast to the previously reported C-N coupling reactions the present reaction works under solvent- and base-free conditions, and the coupling reaction is accomplished in just 6 h with a high yield of the coupling product. The present methodology was also found to be efficient for a wide variety of functionalised aryl halides, and aliphatic or aromatic amines (1° and 2°). Moreover, the reaction also enables the C-N coupling of electron-withdrawing substrates and base-sensitive functionalities.

Cp*Co(iii) and Cu(OAc)2bimetallic catalysis for Buchwald-type C-N cross coupling of aryl chlorides and amines under base, inert gas & solvent-free conditions

Srivastava, Avinash K.,Sharma, Charu,Joshi, Raj K.

supporting information, p. 8248 - 8253 (2020/12/29)

A strategy involving bimetallic catalysis with a combination of Cp?Co(CO)I2 and Cu(OAc)2 was used for performing Buchwald-type C-N coupling reactions of aryl chlorides with amines. The reactions proceeded at 100 °C to produce excellent yields of many of the desired C-N coupled products, in 4 h, under aerobic reaction conditions. The reactions were shown to run under base-free and solvent-free conditions, enabling this strategy to work efficiently for electron-withdrawing and base-sensitive functionalities. The presented methodology was found to be equally efficient for electron-donating functionalities as well as for primary (1°) and secondary (2°) aromatic and aliphatic amines. Moreover, the products were easily separated through the extractions of the organic aqueous layer, with this process chromatographic separations is not required.

Copper(ii)-catalyzed c-n coupling of aryl halides and n-nucleophiles promoted by quebrachitol or diethylene glycol

Chen, Guoliang,Chen, Yuanguang,Du, Fangyu,Fu, Yang,Wu, Ying,Zhou, Qifan

supporting information, p. 2161 - 2168 (2019/11/25)

Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-Arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C-N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.

Decarboxylative ipso Amination of Activated Benzoic Acids

Pichette Drapeau, Martin,Bahri, Janet,Lichte, Dominik,Goo?en, Lukas J.

supporting information, p. 892 - 896 (2019/01/04)

In the presence of a bimetallic Pd/Cu system with 1,10-phenanthroline as the ligand and either air or N-methylmorpholine N-oxide as the oxidant, electron-deficient benzoic acids undergo oxidative decarboxylative coupling with unprotected amines. This operationally simple aniline synthesis is widely applicable with respect to the amine and gives good yields, even on multigram scale. The orthogonality of this reaction to other Pd-catalyzed cross-couplings allows the concise synthesis of multisubstituted arenes by sequential C?C, C?Cl, and C?N functionalizations. Mechanistic investigations suggest the intermediacy of a hypervalent Pd species.

A Structure–Activity Study of Nickel NNN Pincer Complexes for Alkyl-Alkyl Kumada and Suzuki–Miyaura Coupling Reactions

Di Franco, Thomas,Stojanovic, Marko,Keller, Sébastien Carlos,Scopelliti, Rosario,Hu, Xile

, p. 830 - 847 (2016/11/11)

A new series of Ni NNN pincer complexes were synthesized and characterized. The main difference among these complexes is the substituents on the side arm amino group(s). No major structural difference was found except for the C–N–C angle of the various substituents and the ‘pseudo bite angle’ of the complexes. Four new complexes were efficient for the alkyl-alkyl Kumada reaction of primary alkyl halides, and among them, one complex was also efficient with secondary alkyl halides. The influence of the substituents on the catalytic performance of the Ni complexes in alkyl-alkyl Kumada and Suzuki–Miyaura cross-coupling reactions was systematically investigated. No correlation was found between the catalytic activity and the key structural parameters (C–N–C angle and ‘pseudo bite angle’), redox properties or Lewis acidity of the complexes.

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