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N-Benzyl-4-nitroaniline is a chemical compound characterized by the presence of both amine and nitro functional groups attached to different positions within its molecular structure. It is known for its distinct yellow color and is a substance that can be synthesized in a laboratory setting with relative ease. The chemical formula for this compound is C13H12N2O2. Its reactivity, particularly due to the nitro group, makes it a versatile compound for various applications.

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  • 14309-92-3 Structure
  • Basic information

    1. Product Name: N-benzyl-4-nitroaniline
    2. Synonyms: N-(4-Nitrophenyl)benzenemethanamine;N-(4-Nitrophenyl)benzylamine;Benzenemethanamine, N-(4-nitrophenyl)-;Einecs 238-249-4;p-Nitro-N-benzylaniline;N-Benzyl-N-(4-nitrophenyl)amine
    3. CAS NO:14309-92-3
    4. Molecular Formula: C13H12N2O2
    5. Molecular Weight: 228.25
    6. EINECS: 238-249-4
    7. Product Categories: N/A
    8. Mol File: 14309-92-3.mol
  • Chemical Properties

    1. Melting Point: 147 °C
    2. Boiling Point: 392 °C at 760 mmHg
    3. Flash Point: 190.9 °C
    4. Appearance: /
    5. Density: 1.258 g/cm3
    6. Vapor Pressure: 2.36E-06mmHg at 25°C
    7. Refractive Index: 1.658
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 0.31±0.20(Predicted)
    11. CAS DataBase Reference: N-benzyl-4-nitroaniline(CAS DataBase Reference)
    12. NIST Chemistry Reference: N-benzyl-4-nitroaniline(14309-92-3)
    13. EPA Substance Registry System: N-benzyl-4-nitroaniline(14309-92-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 14309-92-3(Hazardous Substances Data)

14309-92-3 Usage

Uses

Used in Dye Production:
N-Benzyl-4-nitroaniline is used as a chemical intermediate for the production of various dyes. Its reactivity, especially under reduction conditions, allows for the creation of a wide range of colorants used in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, N-benzyl-4-nitroaniline is utilized as a building block for the synthesis of certain drugs. Its chemical properties make it a valuable component in the development of new medicinal compounds.
Used in Rubber Chemicals:
N-Benzyl-4-nitroaniline is also employed in the rubber industry as a component in the formulation of rubber chemicals. Its properties contribute to the enhancement of rubber products' performance and durability.
Safety Precautions:
Due to its potential to cause harm or irritation, N-benzyl-4-nitroaniline should be handled with care. It is important to avoid eye and skin contact and to prevent inhalation to ensure the safety of those working with this compound.

Check Digit Verification of cas no

The CAS Registry Mumber 14309-92-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,3,0 and 9 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 14309-92:
(7*1)+(6*4)+(5*3)+(4*0)+(3*9)+(2*9)+(1*2)=93
93 % 10 = 3
So 14309-92-3 is a valid CAS Registry Number.
InChI:InChI=1/C13H12N2O2/c16-15(17)13-8-6-12(7-9-13)14-10-11-4-2-1-3-5-11/h1-9,14H,10H2

14309-92-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name N-benzyl-4-nitroaniline

1.2 Other means of identification

Product number -
Other names EINECS 238-249-4

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:14309-92-3 SDS

14309-92-3Relevant articles and documents

Nucleophilic Aromatic Substitution Reactions in Water Enabled by Micellar Catalysis

Isley, Nicholas A.,Linstadt, Roscoe T. H.,Kelly, Sean M.,Gallou, Fabrice,Lipshutz, Bruce H.

, p. 4734 - 4737 (2015)

Given the huge dependence on dipolar, aprotic solvents such as DMF, DMSO, DMAc, and NMP in nucleophilic aromatic substitution reactions (SNAr), a simple and environmentally friendly alternative is reported. Use of a "benign-by-design" nonionic surfactant, TPGS-750-M, in water enables nitrogen, oxygen, and sulfur nucleophiles to participate in SNAr reactions. Aromatic and heteroaromatic substrates readily participate in this micellar catalysis, which takes place at or near ambient temperatures.

Heterostructured Hybrid rGO@α-MnO2/rGO@δ-MnO2 Nanoflower: An Efficient Catalyst for Aerobic Solvent-Free N-Alkylation Reactions and Energy Storage Material

Chaudhuri, Haribandhu,Karak, Niranjan

, p. 1617 - 1629 (2020)

A new reduced graphene oxide (rGO) based bi-phasic crystal of MnO2, namely α-MnO2 nanorods and δ-MnO2 nanoflakes containing heterostructured hybrid nanoflower rGO@α-MnO2/rGO@δ-MnO2 has been fabricated through a facile hydrothermal method followed by annealing treatment. The successful synthesis of the hybrid material was studied by XRD, Raman, BET, FESEM with EDX, FTIR and TEM analyses. An efficient N-alkylation reaction of substituted aromatic amines with aromatic alcohols was carried out under solvent-free aerobic conditions in the presence of catalytic amount of rGO@α-MnO2/rGO@δ-MnO2. The catalyst shows excellent activity in terms of high yields (up to 98 %), short reaction time (10 h) along with a simple work-up process. The spent material can be regenerated several times without causing any serious decrease in catalytic activity. Moreover, cyclic voltammetry (CV), galvanostatic charge-discharge (GCD), and cyclic stability techniques were executed to evaluate the performances of rGO@α-MnO2, rGO@δ-MnO2, and rGO@α-MnO2/rGO@δ-MnO2 as energy storage materials. Among all those materials, rGO@α-MnO2/rGO@δ-MnO2 exhibited a proficient specific capacitance, CS (267 F/g at 1 A/g) along with excellent cycling ability (~83 % retention up to 10000 cycles). The superb electrochemical performance of rGO@α-MnO2/rGO@δ-MnO2 might be ascribed to the combination of bi-phasic α-MnO2 and δ-MnO2 with rGO sheets, resulting in a flower-like structure.

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

Fan, Qing-Hua,Liu, Xintong,Luo, Zhenli,Pan, Yixiao,Xu, Lijin,Yang, Ji,Yao, Zhen,Zhang, Xin

supporting information, p. 5205 - 5211 (2021/07/29)

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

Trimethyl Borate-Catalyzed, Solvent-Free Reductive Amination

Ramachandran, P. Veeraraghavan,Choudhary, Shivani,Singh, Aman

, p. 4274 - 4280 (2021/03/09)

Solvent-free reductive amination of aldehydes and ketones with aliphatic and aromatic amines in high-to-excellent yields has been achieved with sub-stoichiometric trimethyl borate as promoter and ammonia borane as reductant.

Nucleophilic aromatic substitution reactions under aqueous, mild conditions using polymeric additive HPMC

Ansari, Tharique N.,Borlinghaus, Niginia,Braje, Leon H.,Braje, Wilfried M.,Handa, Sachin,Ogulu, Deborah,Wittmann, Valentin

supporting information, p. 3955 - 3962 (2021/06/17)

The use of the inexpensive, benign, and sustainable polymer, hydroxypropyl methylcellulose (HPMC), in water enables nucleophilic aromatic subsitution (SNAr) reactions between various nucleophiles and electrophiles. The mild reaction conditions facilitate a broad functional group tolerance that can be utilized for subsequent derivatization for the synthesis of pharmaceutically relevant building blocks. The use of only equimolar amounts of all reagents and water as reaction solvent reveals the greenness and sustainability of the methodology presented herein.

Rate and Yield Enhancements in Nucleophilic Aromatic Substitution Reactions via Mechanochemistry

Andersen, Joel M.,Starbuck, Hunter F.

, p. 13983 - 13989 (2021/04/02)

A variety of nucleophilic aromatic substitution reactions were carried out mechanochemically to great advantage. On average, reactions rates were nine-times faster. The corresponding kinetic studies presented provide the clearest head-to-head kinetic comparisons between mechanochemical and conventional systems at identical temperatures. Attempts are provided at classifying the kinetics of one example. Removal of polar, protic solvents from these reactions presents environmental benefits to a reaction class whose kinetics are heavily dependent on such solvents.

Nickel?Copper bimetallic mesoporous nanoparticles: As an efficient heterogeneous catalyst for N-alkylation of amines with alcohols

Nasresfahani, Zahra,Kassaee, Mohamad Z.

, (2020/10/30)

A bimetallic catalyst (Ni/Cu-MCM-41) is prepared via co-condensation method. The latter is characterized by Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), diffuse reflectance spectroscopy (DRS), and nitrogen adsorption–desorption analysis. Catalytic performance of Ni/Cu-MCM-41 is probed in N-alkylation of amines with alcohols through a hydrogen autotransfer process. Noteworthy, this catalytic system appears very efficient for synthesis of a range of secondary and tertiary amines in good to excellent isolated yields. Moreover, the catalyst is successfully recovered and reused four times without notable decrease in its activity.

Iron-Catalyzed Oxidative Amination of Benzylic C(sp3)–H Bonds with Anilines

Song, Yan-Ling,Li, Bei,Xie, Zhen-Biao,Wang, Dan,Sun, Hong-Mei

, p. 17975 - 17985 (2021/12/13)

Iron-catalyzed oxidative amination of benzylic C(sp3)–H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) is realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of the iron metal center. Using DTBP as oxidant, [HItBu][FeBr4] showed the highest catalytic activity for anilines bearing EWGs, while [HIPym][FeBr4] was more efficient for EDG-substituted anilines. This work provides alternative access to benzylamines with the advantages of both a wide substrate scope and iron catalysis.

Catalyst- And solvent-free efficient access to: N -alkylated amines via reductive amination using HBpin

Bauri, Somnath,Pandey, Vipin K.,Rit, Arnab

, p. 3853 - 3857 (2020/07/27)

A sustainable approach which works under catalyst- and solvent-free conditions for the synthesis of structurally diverse secondary amines has been uncovered. This one-pot protocol works efficiently at room temperature and is compatible with a wide range of sterically and electronically diverse aldehydes and primary amines. Notably, this simple process offers scalability, excellent functional group tolerance, chemoselectivity, and is also effective at the synthesis of biologically relevant molecules. This journal is

Cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ

Xiong, Ruimei,Hussain, Muhammad Ijaz,Liu, Qing,Xia, Wen,Xiong, Yan

supporting information, (2019/12/11)

A cross dehydrogenative coupling strategy for allylation of benzylanilines promoted by DDQ is reported, which uses nonmetallic quinone DDQ as an oxidant in the allylation of N-benzylanilines under mild conditions. C–C bond with high selectivity and activity was constructed in this reaction and homoallylic amines were obtained with yields of up to 99%.

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